ǰλãҳ >> Դ/ >>

лӦ(2)-The Merck Index 12th


ORGANIC NAME REACTIONs

o Mo
/

ڥ L .
cJ 2L)

orgaic Name Reacons
e Organ Name Reactons(oNR)secuon intended to serve the professonal cheIIu
and student by descobing organic chen ca1reactions which have come to be recogmzed and refeed to by narne wi in ڥ@ (1983), the che ustry co ununity since d s sccuon1ast appeared in Merc,kJ d,7b many new naIne reac ons have suJaced in the che uca1 terature.A se1ect group has been choscn for ad-

tolis secuon.Each reacuon descopuon is designed to be infomadve and representauve of the mprehensive.The dcsc pdons are composed ofthe fo11owin (1)naIne6)associated wi e reacuon, )thc m nal and/or prImary condbutor(s)con~
diס on

peJ nent li ramre;howeve it is not rneant to bc c
nected wiɽ e dscovery and/or deve1opment of



e reacuon,o)a concise desc

pdon of

e iansfoIIIIa-

ng uon,emphasizing such reacjon paraIneters as sta matcna1s,reagents,products,inteI 1edatcs,rnechons,tzl)a reacdon scheme,6)key references,and6)Cross an m,appI aton,and/or reacton conɽ s refcrcnces to oɽ er ONR based on cOIImona1i es,Inc1uded in the back of secuon is an indcx w ch
also1ists supp1ementary teI
.s.

Abbre"a o s

Ac
BBN
BINAP

acety1
borabicyclo[3.3.1]nonane
2,2 bhaphthyl
buty1
-bis(ɽ pheny1phosphino)-1,11-

E
ee

electoph e
enanJomenc excess

Et
EWG

ethyl
electron withdrawing group

BOC Bu
cat

r-buty1oxycarbonyl catalyuc cyc1opentadienide dibenzy deneacetone
c1icyc1ohexylcarbo Iii dc

HA protic acid HMPT hexaIneɽ y1phosphooc Ѫde

Cp
dba

LDA thium LHVIDs thium Mc methyl
NuH
Ph Pr
salen Tf
Ts

dhisopropyIaImde hexaIne y1do azide

DCC DEAD DME
dppf

nuc1eop 1e
pheny1 propyl
` 1 Lethylenebi salicylideneiѪnc) "i uorome anesu1fony1
r,-to1uenesu1fonyl

diethy1azadicarboxy1ate

dimeɽ ylether pheny dch1oro[1,1Lu ɽ
phosphino)feocene] 1,3-bis(dipheny1phosphino)propane

dppp

organic Name Reactions
217

Kr0hnke Pyridi e synthesis L zccher,RK hnke,B r94,690,698(1961); ,A g C ,E 1,626(1962). ` nium mcthyl ketone salts to unsaturated kctoncs,gencrating the1, dcar1, Miɽ acl addton,g`,oftX py ɽ , bonyl compounds which undergo ammoniu 1acctate-promoted ring closure,to yield substitutcd pyhdines:

ߵ@
Br^

0


R3 R2

NH^0AC,HoAC or MeOH



R2

430(1977);G.R.Ncwkomc J,,Jo
synthcsis.
218

C m5 850(1986);R Lhot k,A.KurOurst,CbJJ,Cz cJ9 C Co9,9P,, 57, 1937(1992) Cr Chichibabin Pyridine synthesis;Guareschi-Thorpc Condensation;Hantzsh(E)ihydro)PyHdine

Early rc cw:RK

hnke, s 1976, 24.synthet appl atons JN.Chatte Ca Ϧ rJ9 l,r9,dj Jc 15B,

Kucherc,v Reac on M.Kuchcrov,z,

`14,1540(1881), Hydration of acctylenic hydrocarbons vith d ute sulfuric acid in the prcscncc of mercuhc sulfatc Or b
H l c l H

ron tri

uo-

"dc as catalyst: һ C C-

+H20

HgsO4~

һһ
C " o

_

Ϧ R fA D,Petrov,Jw Kh9 21,250(1952);MM0cque l,A ,C j rf ڢ sl8,157(1963);M.M. Khan,A.E.Ma1ell, o ogٵ o sCԻ ϫsjs Dy fIfe J Cor,9J,J x s voI.2(Academic Press,New YOrk,1974)p1974; Bs.Kmpin,AA,Petrov,JC C .I/ssR33,3799(1963);W1L Buddc,R E Dessy, r rrers1%3, d 651;JA .C soc Bs,3964(1963);K G Golodova,s I Yakimovich, .o , 2015(1972)ExtCnsion .C r/ssR32,1740(1962) to allenes:A.V Fcdorova,A A.Pc o JC
219

Kuhn nterstein Reaction û R Kuhn,A.Wnterstein, J`C jm Ac 11,87(1928)
Conversion of l,2-glyco1s into

ole ns by reaction with diphosphotetraiodide (P2I4) or other halogenatcd Իs

rcagcnts This reaction is uscfu1in thc prcparation of polyenes:

R Rһ R~R
0H Kuhn ɯJ,,B r71,1510(1938);84,566(1961);88,309(1955);InhofCn
`

0H

J,^P9

684,24(1965).

220

Ladenburg Rearrangement
A,Ladenburg,B `16,410(1883);A Thennal rcarrangcmcnt of an alkyl-or bcnzylpyridinium hahde to an alkyl-or benzylpy
.247,1(1888)
dinc:

R

X

- l R

0

R+



+ Hx

J.H Brewstcr,E,L,E cl,@rg R Ϧc 7,135(1953);L.E.Tcnenbau in Klingsberg,Ed.lIntcrscicncc,Ncw York,1961)p163,
221

JJ 9ad

Jrs D rr v .q,Pt.2,E,

LebedeV Prt,cess s V Lebedcv,Z .oɳ s c Khڥ.3,698(1933).
Fomation of butadiene from ethanol by catalytic pyrolysis,The catalysts uscd arc n1ixturcs of s icates and alun11nun1and zlnc ox1dcs

oNR s3

organic Name Reactions

> 2CH3CH20H -

H2C=CHCH==CH2 +H2+2H20


222

l : մ
m
41,528(1927) ѪbCnzddehyde and a hd cn nc h presence d ͡
c

Lehmstedt TanasesCu ReacJon K Lchmstcdt,B r65,834(1932);I,Tanasescu,B soc,Chڥ ,,,.Frc

l ׼ : ҷ óȡ Ӣ Fu
i

11ys

+ xƲ (
(

))

I.Tanasescu,Z Frenkel,jD 1960,693 Mcchanism
223 Letts Nitr

s bcrg,Frcnkcl,R

`Ro

j C j,,a 10,1035(1965)

E A Lctts,B r5,669(1872)
Formation of ni

e synthesis

by heating aromatic carboxy es

c acids with Inctal thiocyanates: һ )RcN+c02+KHs

RCoOH+KsCN

G.Kr ss,B r17,1766(1884);E, Reid,A .C . 43,162(1910);G.D.van Epps,E E Reid, A C ɨ jscJ9 C I es, rD c d soc 38,2120(1916);D,T MoWry,CJ, m.R `o

(Berlin,1959)p362.

`42,264(1948);EK

224

Leuckart(Leukart)Reaction;Leuckart Wallach Reaction;Eschweile R Leuckart,B r18,2341(1885) R ` һ
/ R

Clarkc Rcaction

Reductive aIkylation of ammonium(or an1ine)salts of formic acid or foman R


+NH4 VCoH



-NHcHo R


R \ ڢ
/ R

dcs by aldchydcs or ketones:

Ⱥ и ҵ
(1933),synthetic appl
ations

E Farkas,C J sunman, 0

C 50,1110(1985);J

Comom9J .23,245(1993)

Ԩ ܺ
(1990)optɽ zed proccdure:R Cadson 47,1046(1993). r J,Ac C/9 sc
225

`
h

Casanova,P Devi,sy

c.
,



Leuckart Thiophenol Reaction r,C .[2]41,179(1890). R.LeuCkart,JPʯ

: W xaRԨ :: ư is



Ѫ pondng ܳ
co


R

oNR 54

organic Name Reac ons
po Ϧ Jz Jr c/a JcϦ
VoI III,809(1955); H,saunders, Av߶ Ϧ cD zo-Co s,? co s(London,1949)p325;D,s,Tarbell,M.A McCall, A C .soc74,48 o (1952);A.R.Fo este JL.Wardcll,Rodd C 1 rD Co I A,422(1971);A sch0bcrl,A `Af,f,JJcԻ FCԻ Wagncr,fro߶ ɳ P,-V,ɴ J9,12(1955), `o '

D s Tarbell,D ,Fukushima,o

I

226

ben Iodofonm Reac on(HaIofonm Reaction)
A.Lieben,A99 (suppl)7,218(1870). Cleavagc of rnethyl ketones with halogcns(mosdy iodine)and base to carboxyhc acids and halofom:

OC߳

+ g_

OCl3

CH3+ Oo a+

R,C,Fuson,B A Bu ,C v15,275(1934);R.N.seelye, A Tumey, C .E 36,572(1959);J, R jc March,Adl, d orgϦ CJ, js` 11Cy-Intcrscʼ ncc,New York,4th cd.,1992)p632;H.0,HOusc,Mt,d ms , C CR o s( LA.Be amh,Menlo Park,Califomh,2nd ed,1972)pp464-465. cr
227

Lobry de Bruyn van Eke stein t ansformation C C.A.Lobry de Bmyn,R ѡ ,14,150(1895);C.A Lobry dc Bmyn,W 262(1897),
c

A,van Ekcnstcin, 195,203;16,

Isomc oization of carbohydrates in alka nc mcdia,considered to cmbracc both epimeI:ization of aldoses and ketoses and aldose-ketosc intcrconvcrsion: H2 H H2 H
C I C I c I R

H-C-0H I H-C-0H I R

H


C=0 I H-C I R

oH

~ HO-C-H

C 0

H o

_
һ

?H
o һ

H2 H

H

H

C 0

H0-C-H

C=0 H-C-0H
R
|

H20H

CHO H0-C-H H-C-oH
R
I

/

R
|

\ c
Ho-C H

/

R
l

H0-C-H
|

R

Rv ws'Evans,C .R v31,50zl(1942);sattlc A'v /J.C rDo y C ,3,113(1948);Pigman,r C rD ~ y (Academic Press,New YOrk,1957)p60;speck,AdvԻ rDod`C .13,63(1958);schaffe Jo .CϦ scr9,151(1976) C .29,1473(1964);M,H,Johansson,o samuelson,C
.

228

V

Lossen Rearrangement Lossen,A ,161,347(1872);175,271,313(1874)
z Conversion of a hydLoxarI1ic acid to an isocyanatc v the intemediacy ofits C,-acy1sulfonyl,or phosphoryl dchvative In the presence of a uncs,ureas are fomcd;in thc presence of watcr,amines containing one less carbon than thc starting matcria1arc gCncratcd:

0
R' `N/

H
ּ


һN=C=

߹N 2 :'N
0
`` R/
Ѿ

H

``



H

c



RNH2

0

Early rev ws H,L,Yalc,C R v33,209(1943);L.Baucr,0.Exner,^ g E 13,376(1974). ˷ , Applic on e stmcturd analy ofpe des:J? T qapccchi r J,Jo ^C 14(19g3).Inve gatIOn of sJs1989,61 Extcnuon to`v~phosrcaction condi ons leading to the foHnation of ureas:J,Pihulcac,L Baue n phinoylhydroxylamincs:J Fawcett J J,,C . ߶ ,1992,227.R r II shio ,Conr,,o . ,6,82 825 ` (1991)( Cu ius Rea angemen Hofmann Rcact n;schmidt Reacton,
229

J s.McFadycn,T s stevens, C .soc.1936,584
Base catalyzcd themal deconnposition of acylbenzenesulfonylhydrazines to aldehydes:

cFadyen stevens Reaction ѹ

oNR s5

organic Name Reactions

o
̰

0
NHNHs 2

R H

? F a
;
23 y

:i|||{ح

|{

{

|1 Fi :



:F

e

; i; :

ny1compounds :

having a hydrogcn h theܳ pos io to an cnd

fra

ment and an olenn


:


l||l|;i|

oH

R c߳

CH2

r

:
(19sOl,CѾ

No sh

Type Clcavagc


ֺ
m

tи ѿ 1f W
һ
L~.

))==<(

Ti

om 0)r Ti(O reagent sformed ln s

TiC|3(DME)15+zn/Cu or TiC13+LiA|H4

R



l:Ʒ f

J &M а
1
cd ǿ 1 h am

ll ;:;

o ;:;

c

I:

232 l adeIung

w

synthesis

P hgh teInperaa re:

cychz n of m G heߵ Ddkan de by a stong bascݶ

CH3P N/C`R
H

360
3:0

~

Na0C2H5



R

q roӡ cF Co/mr,o ds,A Wcissbcrge Ed,,JmdoJ s, W1J.Houlhan,Ed, C R K Brownin r js ٢ J9946,4511,4515(1981), C (Wi1ey,New YOrk,197 pp38 396;V"J Houlihan

`,Jo

IailIard Reaction C 233

BrOWning Reac on)

ܡ :
Forrsc
c c.(Bn7 Jl53,707-712(1981);Moj a R o,9in Food Proc Int sympo um,Uddes,Cj Bobbio,Am^cϦ B va a,swcden,1979,C E ckson,Ed,(Pergamon Prcss,Ncw YOrk,1982).

rC ,Forsc ,14,431(1970);H.E.Nurstcn,

Ρ ߦ
RCH0HCHOHRi+HI04
RCH0HCHNH2Ri+Hlo4
RcH > -

ץ

9

+R CHo+H20+HI03 RCH0+R.CH0+NHO+Hlo3

oNR s6

organic NaIne ReaCtons
g jc @rЭ W1Bentley in E c orC

sDy P ys c JcԻ J^ odb,R2,KW1Bcntlcy,G,W1Kirby, ' Reaction. Eds( 11ey.Ncw York,2nd ed,J973)pp177-185. C egee 'CJ9
srr,c`߶

c s(WA,Be amin,Mcnlo H,0.Housc,Mo rn.9yJo 0cR

Park, California,2nd ed,1972)pp353-359;K

235.l alonic Ester syntheses
synthcses bascd on the strongly activated lnethylcnc group of Inalonic estcrs vvhich on rcacJon with sodiu
read y decarboxylate to mono-or disubstitutcd monocarboxyhc acids

1cthoxs

mef ms a resonance-stabilizcd on that can bc alkylated or acylated.ARer hydrolysis,thc frce akylmalonic ac

H5C200CCH2OC2H5





H5C2 ccHRoC2H5

RCH2 oH

c H,0 HOuse,fIfod r,,s, rJ' fC R Ϧ jo s(W1A.Be amin,Menlo Park,Califor a,2nd ed,1972)pp51 518, s 756-761.Use of crown ethers as catalysts:D.H Hunter,R A Pery,n 1977,37 q Per n Al yd synthe-

s1s,

236 l annich

Reaction L K osche,Ah P

C,Mannich,

.250,647(1912)

Rcaction of compounds having an active hydrogcn with non-enohzablc aldchydcs and ammonia or primary or secondary an1ines to give a 1inomcthylated products(Manni h bases):

CH3)2NCH2CH2COCH3+H20 (CH3)2NH+ HCHo+CH3C0CH3=
Re c 1,303(1942);H.0.House,fIrode sym c RccrЭ s(w1A BcnJamin, Early Mcw RRB"kc,o .2)pp65 l,J Mcnlo Park,Cd mi 2nd cd,197:phen Development of astereosclec ve methods PC.B Page Ի Org, substrate D,A Leigh,R Limanc, J Կ , ⻡ rreԡ m,5639(l993). C %ss,6902(1993).Psub m Applicadon to the synthcs of nyl ;h ߵ h natc H.Kraw yk,s9 Co 24,2263(19%).R wy M Tranlonj J,o L.An m, rrc ,l991-:~s,(1990 E F Kleinman,CoP@ 2,g9 9~sl(199I);H.Hoane,jD 9s~s973;L E Oveman,D,J,R ca, l7~1 6. Bet RCac Robinson-sch0pfRc jon,

,

237.~IarschaIk Reaction
C.Marschalk

^m.Frc c 3,1545(1936). rϦ l,B9JJl soc,C sodium dithionite rcduction of1-hydroxy-or a 1inoanthraquinones to thcir lcuco-fonms,followed by condensation nonesɯ eld l-alkylatcd products: with aldehydcs toɯ cld thC2-alkylatcd anthraquinones,2-Hydroxyanthraq

X=oH, =0;X=NH2,Y NH

r ;;;ft Aد::8: 20,2691(1990);N.R.Ayyangar Ի Co
`

:

44, (19ssl syntheuc mcado R z Ϧ l,J 62,1922(1984);M. Fudong er l,s, 1,C 31B,3(1992)

J

ֹ C ˷

,

J C

`,,r9

238

~Iartinet DioxindoIe synthesis d156,1625(1913). A.Guyot,J,Martinet,Cb,,9I, R Fomation of deHvativcs of dioxindole fron1estcrs of Fnesoxa c acid and aromatic an1incs or amlno quino

ncs

V
0

R

R

J Martinct,fɳ j 1,851,998(1918);A P1.C J .[9]11,85(1919);W Langenbeck r J,^P,/,499,201(1932); rϦ l, ro yC jCb` 3,239(1952) ds? 512,276(1934);W1C.sumptc C ,R `37,472(1945);R L Julian `o oNR 57

organic NaIne Reactions
239

Meerwein AryIation
l, P C 152,237(1939) H,Mccrwein Ϧ
Arylation of oleflns by treatlnent with diazoniuna salts in the presence of cup c salts:

z-C=C- |ɽ

ArN g

cuc12

~

z~c=c_
r

z=C=C,C=0,Ar,CN,H
c R v sJ C.s.Rondcstvcdt,J ,@' .R 53,1065(1980). Pscho Rcaction JcpϦ

11,189(1960);jD 24,225-259(1976);s,Oac J,,B soc ,C m

240 l eerwein

.4,22 (1925);WP nndoH1Am8 wC 39,138(1926);A,Veney,B H,Meerwon,R schmidt,A
C J Frn C 39,537,871(1925),

PbnndorF Verley Reduction

JJ,soc,

Reduction of a1dehydcs or ketones to thc corresponding alcohols with alun
naucr oxidation,-z.1^)

num alkoxides(the reverse ofthe oppe-

RѾ O



+%CYCH oH

l CHlCH J3

RѾ OH



+߳ o



cH

crЭ s(WA,Be amin,Mcnlo hrk, c A L Wilds,o0 R Ի 2,178(19 );H.0,HOuse,lro rJc R rԻ CalifomIa,2nd cd,1972)pp68,154,155;R,MOn ag J.,JoѼ o JC .50,C15-C17(1973);J,Hutton, ,198 192;R,M.Ke11ogg,Comp.Org.s, 88 91(1991), sy Co .%483(1979);L Home u B.Kaps,^ Cannizzaro Re on; schcnko Reacton,
241 lѹ eisenhei ner

Rearrangements
[1, -R

J Mcisenhcimcr,B r52,1667(1919)

Form on of0, - substituted hydroxylamines from te iary amine o des v
'
o


group m m on,or

[2,3]-sigmatrop rcarrangemcnt when Ri=?ally


ߵ
`

+

R
R'



N-oR, ;
R '

ؼ'
` R

C

`R

293(1988);R Yoneda

rϦ dr0 [1,2 RCarrangemcnts N Castagnoli,J J, rrn

Ϧ J, rrc d

26,4319(1970);J,B,Brcnlncr ,A s JC .41, rs35,3749(1994),( stCvCns Rearrangcmcnt; 2]-Wi ig Rc-

` arangemcnt, ,3 RCa angemcnts V Rautenstrauch,ffe``C f Ac 56,2492(1973);Y Yamamato .,Jo碹C .41, r߶ 303(1976);T Kuhhara rϦ J,,C ,P B߶ J 42,475(1994) slow-Evans Rearrangemen sommelet-

Hauser Rcarangemcn1 ,3]-1ttlg Rcarrangement.
Apphcation of both rea angements
242
id rϦ o
`,,

j ɳ 31.

Ienschutkin Reac on

N Menschutkin,zP vsI

C

5,589(1890);6,41(1890)

Reaction of tcѪ ary amincs with alkyl halidcs to fom quatcmary salts:

R3N+RiX



R3RtN+x

M,H.Abraham,Prog`P ys,Org,C .1 1(1974);E,M.Amett,R Reich,J^˷ 1ers,JC schug,j3 i104,850(1982), L
243

cC c C K Ingold,s` ߷ Ի d c Ϧ js 0 Js` (Comell univ Press,Ncw York,2nd cd,,1969)p435;

C .soc102,5892(1980);J.

Ierri eld so d Phase Pep de sy thesis C R,B Menofleld,JA soc.85,2149(1963),
:i
l ;

u: ܼ ȹ ; Ⱥ 1dz ڡ
:Flͣ
:

sdu~

oNR s8

orga ic Name ReacJons


ongation step:
R

R?

` r o



: cHN' `w' N


H
R

O
DCC
R

` r "




o "

N H


' һ

N H

C

1 CF3COoH
2 NEt:

` r o

N

O
"

N
(ste

' һ

s repeated)

"˭ pp Autob graphic account B,Merrlnc1d,
6247(1993)Appli tion D,D,smith J
rjv

Book C Birr,^sr crs f

Washington,D.C ,1993)pp54-118,Method for mo toong synthcs
PcP j VoI 1, lL Vn ams,D,B Weiner,Eds s `.,r,9

Pef, sy sjs,K Hafncr r J,,Eds.(spHngc Vcdag,New York,1978 102 g Co Ag grPepڥ C d ߡ JI seeman,Ed(ACs, JϦ D ڢ
:B

D Larsen r J,,J^˷ .C soc115,

J PeJ, Pror R s,44,183(1994),B ef review B,orog cϦ JJ,Ac d

(Tcchnomic,L ncaster,Pcnnsylvania,1993)pp115-121,144-

147,
244 l eyer

Reac on G Meye B r16,1439(1883)
Preparation of alky1stannonic acids by reacting alkali stannitc with an alkyl odide Whcn applied to alkali arsenites
or plunnbites thc rcaction yiclds alkylarso

ic and alkylplumbonic acids,rcspectively:

Na2sn02+ RX
Na3AsO3+RX

RsnO2Na+NaX
RAs03N +NaX

W1R Cullcn,A'vϦ .0
245 lѹ eyer

Ϧo

J.C ,

I48(196

schuster1Rearrangement;Rupe Rearrangement

-acetylenic alcohols to Aci(I atalyzcd rcarrangcmcnt of secondary and tedary pounds aldchydcs whcn the acctylenic group is terlnina1kCtones vhen it is intcma

K,H Mcye ,schustc B r55,819(1922);H

Rupe,E,Kambli,ffe

C ,Ac

9,672(1926),

unsaturatcd carbonyl com,

OH
R2CC CR1- ~R2c=cHc
I

Ri

Thc convcrson ofteѪ ary alkylacetyle c carbinols with a teminal acctylenic group predominantly ed to as the IRupe rearra gement: ratcd kctoncs and not the expected aldchydcs,is rcfe

unsat ,

OH
RCH2

0-C
R

CH

ƥ ͡ ر

R-CH=CR(C0CH3

R

rPrJ s,8,178(1963);s A Vartanyan,s.0,Babanyan,R ss CJI han,K.V Narayanan,C ,R v71,429(197D;M EdCns rԻ l, o C .42, `36,670(1967);s,swaninݶ 3403(1977); .E stevens,P Yates,C .Co˷ ߶ 1980,990.Titanium/coppcr or silver based catalysis:P
R ws

R Holmann,R Glenat,A
d rre

.

Chabardcs,
`
246

29,6253(1988).

`

Meyer synɽ esis( ctor Ieyer synthesis)
1Mcycr,o stube
FOrmation of a
B

r5,203(1872)
? iltes

phatic nitI

and nitro dc vatvcs by the reaction of ahphatic halides with metal nit

tes:

RX+MNO2 R0N0+RN02+MX

(1943);N.
E,D
247

R.B,Reynolds,H,A ns,J^ ,C .s 5 279(1929).R vJ wsJ H,B,Hass,E R Riley,C .R `32,373 c omblum,o ,R 12,10 156(1962).Appl a on to thc synth of dinitroalkancs:J,K.stille, ,
c

Vesscl,Jo C .25,478(1960);G.Leston,o .sv 368(1963). C
`,,J^

Meyers Aldehyde synthesis

A I Meyers r

38,36(1973), soc,91,763(1969); ,J@ C

oNR s9

organic Name Reactions
synthesis of aldehydes from alkylhal es and2-lithomethyltctrahydr oxa ne:

c¬ ή

J,J@n Ի
248 lѹ ichaeI

ԻCH9CHo «

c J.March,Adv dC Ϧ Jc C s (1Viley-Intcrscicncc,Ncw YOrk,4th cd ,1992)pp478-479;A,I,Mcycrs C 46,783(1981),

ReacJon(Addition,Condensation)

AM hacl,JP C ]35,349(1887), Baspromoted co uga addidon ofcarbon nuclcophiles(donors)to activated unsaturated systems(acceptors):

l 'د I

ح

1

+
F Fi



ݦ

Ƚ


unds,sulfones

donor=maIonates,cyanoacetales,aoetoaoetates,cafboxy"c esters,ketones,aldehydes,n""Ies,nitro comp ic a ids,n""les unsaturated ketones,0sters,aldehydes,amides,carbox߶ acceptor= ,
sur xides,su fone

base=Na0CH2CH ,NH(CH2CHol2,K0H, oC(CHOl3,N(CH2CHOl3,NaH,BuLi,LDA
R vj ws;E

,nitro oompounds,phosphonates,phosphoranes

A.BenJamin,Menlo Park,California,2nd ed,1972)pp595-623;M,E.Jung,C mr,@

D Bergmann

ԻJ.,o R cɯ ,10,179-555(1959);H,0.Housc,Mt,d

rn

ɯ R c jo sO JC

tension to organometa11ic nuclcoph es: 1J Lee,JDJd69-137,139-168;J,A.Kozlowski,ibid.169-198.Reviews of stereoselectivc synthesis:H.-G schmalz,jDjd199-236;D.A.Oare,C H He hcock,TOf,s oc ,20,87 70 (1991);J.d Angelo r dm rv3,459-505(1992).Cr Nagata Hydrocyanaton;Robinson ^o` Annulation. `,,Ter
249 lѹ ichae s Arbuzov

sy

4, 67(1991)Ex-

ReaCtion A Michaclis,R.Kaehne,B r31,1048(1898);A.E,Arbuzov,
1906,II,1639
niun1sa1t:
P

R ss PJ,vs C? J, s c,38,687(1906);Cn ֡ z rr

Fonnation of monoalkylphosphonic csters from alkyl ha dcs and tHa1kyl phosphitcs,v thc intennediatc phospho һ ~(R

oR)3+R X



(R0) PRբ xһ

P(o)R

-Wɴ J1 1,433(1963);B,A.A uzov,P APPJ, 6,276(1951);K sasse,ffo D R v71,317(1971);G.Baue G.Haegele,A g ߳ C E 16,477 ˷ ? (1977);A.K Bha aCharya,G Thyagar an,C R 81,415(1981).

G,M.Kosolapo

C .9,307(1964);D

cܳ @ R Ϧ

Redmore,C

250 l iescher

l, C.Meystre Ϧ J`C jɬ Ac 27,1815(1944) eland dcgradation,-z. Adaptation ofthe Barbier-
degr? ada on

Degradation

^,to pcrmit simultaneous e1in1ination ofthree carbon atoms,as in ofthe bnc acid side chain to thc methyl kctonc stage,Conversion ofthe methy1ester of the bile acid to the

tediary alcohol,fo11owcd by dehydrauon,br mination,dchydrohalogenation and oxidaJon of thc dicne yie1ds the
chain-shortened ketonc R CHCH2CH2CO0CH3 ǵL~R cHcH2cH2C(0H)Ph2 ƥ׹ һ H2

^

R cHcH2CH=oPh2 (CH2C laNBr~

RRlCHCHBrCH=CP

nhlc=cH-cH

CP һ2ƥL~

Rc +

HCCH=CP%

.soc 1950,3355;A. ,RFr rs.(Chem,soc o ndon) C W shoppee,A ",184(1947);R o C,mJ,o D,26(1970); Wettsteh,G.Anne Eve fjϦ 195 40 C.J 1Brooks,Rod' C s spHng,JC `v PG,Marshall,jDjɳ 233,253,323 `C
251 ignonac
G?

. t i : fign lƷ; the prescnce of a nickel catalyst:
oNR60

ʡ

Reac o
g:I

ܡ cf

|au n f aldehydes or ketones in



quid nunoѪ a and absdute ethand

organ Name Reactbns
RCOR

+NH3+H2

ҵ

RR,CHNH2+H20

E Randvcrc,A sJ r߶ ѫ
252

Djo (B 0sA s,18,81(1948);fro ɳ ~ vJ0,51(1955).

Hydrc,XyIation of OIe ns ѹ as

1 ˺ W ti ʯ


( : lIi::ڥ t11:l :ġ
253

OH0H

%;:

: lС :

s DJF j'V rcJ,s s

isIow Evans Rearrangememt `1g RB kart l,JA ,s c,90,4869(1968);D.A,Evans r J,, 93,4956(1971). Ϧ C



j ǯ jlI;lح Fʢ̯ :i
I ;:T

;} ;:tɻ iح

Ԩ ޼ ⾧t






r
thi

ح

|



phile=P(oCH3)3,(CH3CH2)2NH,pi e"dine,Phs


254 ~ tsunobu
o


Yamada, 2380,

Reaction Mitsunobu r@ ,B Jl

C soc J PϦ 40,935(1967);o.Mitsunobu,



g

r Ӫ Ͼ 1% ::
oH

+ߴ P
۷

ح ߵ

c El

ߵ

߳

I

:?c Ԩ


cOO:һ
߹

+PhaP

NuH=phosphoric rnono and diesters,carboXy c acids,phenols,imides, oximes,hydroXymates,heterocydes,thlols,thloamldes, esters ket

Mcthods developmen J.E Macor,JM.Wchncr, r rocycJ s35,349(1993);R.s CoIeman,EB.Grant, r 5 (l: f1 : ;: : J: 1: 1 ;3;, : j Mitsunobu, y Ի c`,29,1-162(1983);D L.Hughcs, ɳ 42,335-656

Ů ٲ ߹
(1992)

Ʒ

:. ë %;





'sJs1981,1-28;B R,Castro,Org.R

oNR 61

orga"c Name Reac ons
255

Nagata Hydrt,Cyanation r` /c d o,nL rs1962,461 `Nagata

` `,1 Alky uminum-mediated1, add"ion of hydrogcn cyaѪ

dc to



unsaturated ,

-F

carbonyl compounds

Adam r; I
256



: ;F :

;F
R

f

476C97D? sy

h

app c o

T RG aghc

L

Nametkin Rearrangement
s,s Namctkin,A9a,o 432,207(1923),
A special casc of carbonium ion rcarrangcmentin camphcnc hydrochloridc deovatives involving the n1igration of a
methyI group

һ
H

I
Retro9nacol

Rcarrangement;Wagnc Mecrwon Rcarrangcment
25

Ի Henccka,ffo ɳ VJ 2,16(1955);Ps.Mo0rvs l,JA

C ,s c100,260(1978).

1ǿ Ǫѩ ɻڥ: ¯ sssR,o

ƾ Protic or Lcwis aCid-catalyzed clcc͡ oCyc1ic hng cl( ߡ clopentcnones:

: 8\e nԿ , ɽor cq vde q-

o
H3P04




HC0oH

һ
~
\ C H
C

o

բ 1:I:{ ;;% ݶ Ʒ :;è
s 1 PӪ

nC H? T Kang h );K L,Habennas TI l

Ի ,3495 9 rJCrs 158(1994). Ի
o

.

org.R

c

,



T

lm,A

,109fl92 RWN

G Huh, 515,283 9
ethoxidc,fo11owcd by

Formation of -a 1ino ketoncs by trcatment of su1fonic estcrs of ketoximcs with potassiun
hydrolysis

RcH9`12%߸
һ





+



:
259

ߵ .6,78789(1991) .Yamamoto,ComP,@ ,
s9

Nef Reac on

ߦ
H

ketoncs iom p In y and seconda,nioalkancs,respectivcly,by trcat:ncnt of their
ؼ
O " C
R

R

һ
C l N

һR
2

2NaOH~ 2R~cһ

t /



2H2s

4 ^
R

+N20+H20+2NaHSO4

oNR 2

organic Name Reactions

Ʒ ߵ
260

w ָr

;?

۲ f ν1 :ߵ ܶ ɰ: M ;

Nef synthesis J,U,Ne 308,281(1899).
Addition of sodiun1acetyhdes to aldchydcs and ketones to yield acctylenic carbinols;occasionally and erroneously ^ rcfcrred to as the Nef reaction,g.`

ߤ ڿ
g

:

261.Nencki Reaction M.Ncncki,N.siebe J Pm C (2)23,147(1881) The acylation of phcnols with aCids in the prcscncc of zinc chloHde,or thc modiflcation of the Friedel-Crafts ng
reaction,g.`,by substituuon f ferrlc chloHde for aluminum chloridc M Nenckl,W1schmm, j 546;M Nenc , 25,273(1882);U.s Chcma,K Vcnkataraman, C 1932,918;C W schcllhamme fr D -We9,J7 a,284(1973),CF Darzen Ncnitzescu synthes`of Ketones.
262
s c,

Nenitzescu Indo e synthesis C,D,Nenitzescu,B JJ soc,C .Ro 11,37(1929). syntheso of5 ydroxyindole der~at es by condcnsatlon ofpر cnzoquinone with

Hi

:(



R ~

o

-amin croto c estcrs

:


R

ն J ̡ ź и
263

Nen"zescu Reduc ve ACyIation C.D Nenitzescu,E Cioranescu,B r69,1820(1936)
Hydrogenauve acylation of cycloolc ns with acid chloodes in the prescnce of alun1inu 1chlonde;withIve and six-membered rings no changc in ong sizc Occurs but vith seven-mennbered Hngs rearrangement takcs placc with formation of a cyclohexane dc vativc

+ aCOC+ Ѻ  z
264

Nicholas Reaction

R R Lockwood, .M,Nicholas,re d L rrers1977,4163.
reaction of dicobdthexacarbonyI-stabized propargyl caJons with nuclcoph cs,fo1lowcd by oxidauvc demetalhc
ation to yield propargylatcd products:

oNR 3

_

c

/ һ w



orga ic NaIne Reac ons

_
c

һ<
2

һ

c һ

Ρ ߵ

R1=H,siR3,alkyl,a

1R2=H,CH3

H+=HBF4? 0(CHal2,CF CooH;Lewis acid=BF3? 0E ,EtAlCI2,TiC14,Bu2BOso2CF3 NuH=eح dron"oh afomaucs,p~dicarbonyI compounds,ketones,enolates,a"yl olanes,hyd"de,amines,enamines
0 =Fe(No l3,Ce(NH l2(N03l6,(CH3l3No

sV J rJ1992,435;K,D

l,JA C .soc? lO9,5749(1987)scope and nitations .D.ROth, stcrcOchemical study:s.L.schreiber Ի Roth,U.M ller, rrc d' zjerrers34,2919(1993)synthetic applications PA Jacobi,W
wJ

zhcng,j3jd2581,2585;E.Ty e11 r J,,sy J rr1993,769R
(1987).
265

K,M.N ho1as,Accrl9.C

R s,20,207-214

NmentoWski QuinazoIine synɽ eos s.vN mcntowsk,JP C . ]51,564(1895).
Fomation of4-oxo-3,4-dihydroquinazo nes by cyc zation

+ һ C :+zHP
())(
H

of thc reac on products of anthranilic acid and an1ides:

:

0

R vj wsr T A, 11iamson, vcycJ Co Po Jj6,331(195T,;W1L.E Amarego,^dv 1,253(1963);E,Cuny r J,mϦ d L r921,3029(1980)

. ӡ

cJ C

266

Nmentowski QuinOIine synɽ es

s v,Nicmentowski,B r27,1394(1894);28,2809(1895);s8,2044(1905);40,4285(1907).
-hydroxyquino ne derivauvcs fron1anthrani Formation of c acids and carbony1compounds


n 267 Niere s

oH

()1(i

;H +


:i

:

lliamson,ffe٢ c,cJ ComPo 6,331(1957);W1L.E Ar R H,Manske,C ,R `30,127(1942);TA.V l,%rrn Ler rs21,3029(1980) d marcgo,0߶ J Ϧ lInters0cnce,New York,1967)p74;E Cuny Ի s

n FHcdlacnder synthesis;Pfltzingcr Reac

Reac on Ť D.A,Clɽ bcns,M.Nierenst n,JC soc,10 1491(1915).
are obtaincd if an orrho-hydroxy group is present:

Fomation of -chloroacetophcnones by reaction of diazomcthapc in dry ether with aroyl chlorides Coumaranoncs

AC0CI+CH2N2
0C0CH3



ArC cH2cl+N2

+cH9Nz
C0Cl

l
`vcvcl CJ,

WE,Bachman,W1s stmvc,0
268

R Ϧ c

1,38(194 ; M ahara,ֹ

.16,1I47(1979l

Norsh1Vpe CIeavage

R,G.W No ish,C,H Bamford,^ J 138,1016(1936);140,195(1937)
synthetically useful for thc
f

Nush Typc I Cleavage Homolyt cleavagc of aldchydes and ketones o nating from th r cxotcd n statc,
ing cleavage of cyclic ketoncs

oNR 64

organic Name Reac ons
R

һ
O
ll

C R

hv

Ri C? + R?

o
ll

No sh Type Cleavage:Reaction ooϻ nating from the n eXCitcd smte of aldehydcs and ketones thatinvolvcs in-hydrogcn abstraction fo owcd by clcavage ofthe rcsulting diradicalto an olcnn and an cn tramolccular l`vhich tautomcHzcsto the Carbonyl compound


PJ,Wagnc



һ

һ Ȯ =Ѿ

L
Accrs CJ, .R s.

168(1971);JD.Coyle,HA,J,Carless,C .s c,R ɬ
3,197(1973);J.March,A'vԻ

Chapman,Ds.Weiss,o

Ncw YOrk,4th ed,1992)p242. McLafcrty Rcarrangement
269

PJ9 c

d0 jc Cr, ߿ C V(Wiley-Intersc nce,

`1,465(1972);oL.

Noyo Hydrc,genation T Ikaoya Ϧ l,C ,Co ˷ .1085,922;R.Noyo l, A .C soc.108,7117(1986) ˷ HOmogcneous asyѪ met c catalytic hydLogcnation of ` oleflnic and carbonyl bonds lncdiated by enantiopure mthcnium(II)BINAP complexes.The substratcs Inust have coordinݶ ing functionalities in neighboHng positions which
serve as directing groups du1r0ing thc transformation:

ƥ





H






substrates:

m





m
J,/^symmetHc

Det lcd cxpeomental procedure M Kitamura

Mashma


` l,jD 30bZI R j H.Takaya l,^ C .& 230,12 142(1992 m rڢ c Js,I qima,Ed(vCH,NCw YOrk,1993)pp Hydrogcna or in c

l,C, s,,m71,1(1993)Methods dcvclopment for enam e Ϧ l,J0 C 59,297(1994).Developmcnt and use of arene substitutcd BINAP c alysts

`rJc C
270



js 0 ϦJc sv (John Wiley&sons,New York,1994)pp1 ^ s

39;R,NOyo ,Am

94.

oppenauer( da on R.V oppenauc R c.rrc`cJ,j ,56,137(1937).
Thc alununun1alkoxide-catalyzcd oxidation of a secondary alcohol to the co esponding kctone(the revcrse of the

Mccrwcin-Ponndor Vcdcy reduction,g`)

RCHOHR(+CH3C0CH3=اn ~ Rc
T Beresh in rM o w fP

R

+CH3CH0HCH3
Ed(Intersocn0c,Ncw York,194g,p125;

ɯ Org C o rry,English JV Jc

R c CE eras ,o 6,207(1951);L,HOmc u.B.Kaps,A 1980,192.q Cannizzaro Reactlon, ` 271

Oveman Rearrangement ,soc.96,597(1974);9 2901(1976), L,E,Ovcrman,J^ ,C
Fomal l~s,al~siI̦ matro ,ic rcarangement of the t chloroacctimi(latc of allylic alcohols to allylk chloroacct

lides,thcrcby transposing thc hydroxyl and an1ino functions w

h good chirahty transfer:

oNR 5

organic Name ReaCtions

R R
R
11 I
l

h ɻ ² mcchaѪ udes: Eguch ɺ fól 49,4527(1993).( ClaisCn f;; Rearangement. dm templatc and
f
r

:

:

stic

J,, r

R :

R

;:̨

`

272

Oxo Process(Hydroformyla on Reaction)
R
1:ح

tma ? 127, 1 95 @ ,B ? ָ,and hydrogcn in thc liquid phasc in the prcscnce of Catalysts ﲭ Ʒ :ح bonyls)at115-190 and high prcssurcs(100-200atmos.


rϦ ,

(mCta1lic cobalt compounds such as Rancy cobalt or cobalt c

Falbe,Ed,(spHnger Vcnag,Berlin,1980)pp1-225Reppe modincati
A C ˷ .soc.109,7428(1987).

1 JTT

n(olenn+co+H20+Fc(Cols R Massoudi

{

I J
;ح :

273

Paa Knorr PyrroIe syntheş

C,Paal,B r1 367(1885);L Knorr, 299. FOmation of py oles by heating1,4-dicarbony1compounds with ammonia or pornary an1ines in a sealcd tubc

R P Ͳ һ Rࡱ
(1936);A,H Convin,H rocycJ
(1955);H,H Wassermann
s1s

H Fischc H Orth,DJ C J

d s

Pyr Js1(L0p g,1934)p34;D.M

Cb' Po
dv

1,290(1950);N P Buu~Ho

Young,C,RH,^llCn,o .sJ? m16,25
f , 0 C .20,639,850 ole synthes ;Kno Pyrrole synth

r J,, rrc

3z1863(1976),CѾ Hantzsch Py

274

Parham Cyc zaJon

W1E Parham rϦ 0rg,C 40,2394(1975), ,
ng Four-to scven-membcrcd annulation of aryl bron1ides beanng orrho side chains having an clectroph accomp shcd by halogen mctal exchange and subscqucnt nuc1eoph ic Hng closure: ic moicty,


E=C00H,CONR2,epoxide,CH2Br,CH2CI,oCONR


NCHAr,CONRC0CH2R,P0Ph2 ,

: ϳ ح1;J: , );ɭ
:;

:;

:1;

:; :;ڥ f1;

%
:

e d

:u

275 Passerin

M Passerini,C

Reaction frc15 126,181(1921), Fomion oftX hydroxyc xaFmdcs on re mcnt of an`oni b th

+R3C +R

0

m~~
R
N H

a c? drboxylic

^ ~ ^

R Ѿ


R

ac and an ddchydc Or keton

o H + R3COoH

N'{ :

7:: : 1:Ʒ

(1993)R

Press,New York,1971)pp13 143;IU
276

P1 1 ߽Uϻ :If g dz (Academ 1,8(1962);I.Uϻ w 9IU
!?

:

i

I?

,A g C ѫE

Ϧ in Jso J J C o ɯJ ? J,Comr,.o 2,1083 087(1991),

,Ed?

Patemo Buchi Reac on

J,JA,9,.C ,soc,76,4327(1954). IrcJ39,341(1909);G Btchi E Patcmo,G.Chʼ fl,CԻ .Chڥ ǡ
Fomation of oxctanes by photochc ucal cyc1oaddition of carbonyl conlpounds to olcflns:

oNR 66

organic Na1ne Reactions

R /
tcrs,JA
277

߳

R

/Rʢ

3

.6,301(1968);G Jones, D.R.Amold,A ,P orodb s C c,10
Pauson Khand

5,1(1981);s.C.Freil h,K.s.P ,Org P o c 6255(1981);J.A.Porco,J ,s L schrobcr,ComP.o sv 5,15 192(1991).

Reaction

I U.Khand J,,FVrt 9a rrns 1973,977 The formd +2+1]cydoaddi on ofan dkene,alkyne,and carbon monoxide to form cyclopcntcnones:

ܳѪ
278

R



R2

J,JA C soc,11 2153(1994);V Bemardes d ,J@ C ѡ Usc of a chiral auxillary X,Vcrdaguer Ϧ J,9, ,C .soc.116,3159(1994).R vJ sJ N E schore,o1 60,6670(1995).Catalytic version:N.Jeong rϦ .5,1037-1064(1991) R `.,JAڼ c,40,1-90(1991);:& Cb`
Payne Rearrangement
` C,rg s9

G,B.Paync,Jo

C .27,3819(1962) Basc-promoted isomchzation of2,3-epoxyalcohols:

oH
R


R

`

In co unction wi nudeophillc Hng opcning:TK suki rҨ J,,jɳ J 47,1373(1982);CH.Behrens ɯ , j 5 Ի ˷ 5687(1985);RC.B.Page ɯϦJ,,FVrtj TrC s 1990,1375; Konosu l,C P Ϧr B JJ %562(1992).
279

Pechmann Condensation
H

v,Pcchmann,C D sberg,B r16,2119(1883)
synthcs

of umarins by ndensation of phenols w hD keto

esters in the presence of Lew

ysts: ac c

m\u һoǡ
Early reviews s.scthna,C
R v36,10(1945);s.sethna,R.Phadkc,@ 280

0H3

9Lһ
Kappe,E
37,

Zʼ glcr,@ Prer .Pvc 1,61(1969l;T Kappc,C.Maye s 1981,524;A 2021(1981),GF BischlC Na9erals Rea on;simo s Chromone Cyd at n,

c'7,1(1953) R

G,Osbome, r dv

Pechmann PVrazoIe synthesis H.v Pcchmann,B r31,2950(1898).
plc FOrmation of pyrazolcs fron1accty1enes and diazomcthanc.Thc analogous addition ofdiazoacctic cstcrs to thcؿ bond yields pyrazolecarboxy c acid deovatives:

+ 0= ڢ
R

H
roӡ cJJc Co ٢

A.Raphael,^c


`t9

s cC nPo 0 ϦJc sv s(LOndon,1955)p179;T L Jacobs, ᵶ 5,70(1957);B.EisteH ɯԻJ,,Jfo9Jɳ -Wzy`10/0,840(1968).( Kno Pyrazole synthcsis

-

281

PelIizzari React:on

m,Jrd`4 G,PcllLzari,C zz,C ,20(1911). FOm on ofsubѪ 1,2, azoles byɽ c ndens on of atmdes and acyl hydrazines When the acyl groups ofthc amde and mc acylhydraz arc dferent,hterchangc of acyl groups may occur with foѪ aton ofa mkturc of azolcs

oNR 67

orga"c Name Reac
R

o s

'

H +
H

HN

5

NH

N Ϧ Ѿ R


R
alkyl phosphatcs:

:

rk,4ɽ e J950p yJ̺ i : :; YY 渧 I:?t.k :

282

PeIouze synthesis .10,249(1834) J Pelouze,A
Form?ation of nimlcs from alkali cyanides by alky1atioh with alky1sulfates

R0so20K+KCN- RCN+K2s04 mpo ndslNCw ̪ ,19z+9lp f

19i߱
2:

l ;:

,


g

TM

, .R

`42,

:

F 193(1::

mfJ



&

Ѿ u Ѿ
R o

R Ϧ o s( c

1

;

m

ڨ d kan and compoun co סng acλ Ѽ m hy|?e

h

H,o House,ar d rPI s,? J 570. M onic Ester sy theses.
284

1A.Be an n,Inc ,Mcn1o Park,Ca fomh,2nd cd.,1972)pp492

Perkin Reac on

,soc,21,53,181(1868);31,388(1877). W1H,Perkin,JC ˷

g sh : :
CsHscH lCHaCol


m g%of by"ddߵ n ? arom

:d

0y s

mhy

^ /~ o

C6H5CH~CH2C00
CH3C0 0
|

lCH3C0 0~c6H5_cH-CH2

CH3Co-0

C0-0 C0CH3һ

¼ һ

C6H5CH=CHC0oH


? Fomation of bcnzofuran-2-carboxy c acids and benz
;: 3F 1د




;;:

;lsи l;%t;:mm

d

m

M


() (
R

R

)1(

һ

R


c



f

|

Kx-

~ H- ƥ
()

I(

L

()

'R

;

C,Elder cld,V B Mcyer, ӡcJ Cb` po 2,2,5(1951).

oNR 68

organic Name Reactio
286

s

Perkow Reaction
V

Pcrkow l, r s3%353(195 -halocarbonyl compounds with thalkyl phosphitcs: ` FOmation of cnol phosphatcs on trcatnlcnt of

ȡ lOP
cPHs
5


(1980);M sekhe
l,Jo

C .46,4030(1981).



287

Peterson Reac on(oIe nation) D J Peterson, 0 C 33,780(I968) -silyl carbaѪ ons with carbonyl compounds y lding -silylalkoxmcs w ch undcrgo instantancOus Reacton of
eh 1ination to afford oleflns

ˡ

+ ڢ
R

R31

\
J


99 E ,
`o

0H )L
Ρ

L.Bkb

jC 0stʼ hl,ToJ, CJr C .88,58(1980);E.Co1vin,sJJ j OrgԻ s9 s0s(Butterworth,LOn-

aѥ I: %a;$f ׼
288



3:,

Petrenko Kritschenko peridone synɽ esis R Pctrcnko- tschcnko l,B r39,1358(1906);40,2882(1907);41,1692(1908);42,2020,3683(1909) FOmation of pipchdoncs v cyClization oftwo moIes of aldehyde and one mo1e each of acetonedicarboxylic ester z and ammonia or a prirnary a1inc

o

RoOCCHf o
c6߸

CH2c R

o

H

H c

O


R

R
:i

HNH
|

Ri

ffe rocl

J99,soc 111,762,876(1917);C.Mannich,0.Hʼ ronimus,B r75,49(1942);H,s Moshe R Robinson,JC c? C Comr o Jb1,659(NCw York,1950)CѾ Robinson-schopf Rcaction
/

289 Pfau

PIattner AzuIene synthesis A.st,Pfau,P A Plattncr,Jfe`vC jɬ Ac 22,202(1939), ng Fomation of azulcncs by enlargement ofindanes on addition of diazoacetic este
and decarboxylation of thc rcsulting acid:

hydrolysis,dehydrogenation

oNR 69

organic Name Reactions

NaCHC






O

n

3)-Co2

gƪ ޺ Wɡf:i: 1 :f;:Ԩ
1

G sr ec

P l 69

1

l:Ӫ

ߴK

290

PJitzinger Reaction
W

fC ,[2]33,100(1886);38,582(1888), Pfltzingcr,JP
nes

F mau n f quino ne-4 carboxy c acids by condcnsation of isatic acids fronl isa

n with methylcnc carbonyl

compounds;subscqucnt decarboxylation yields quimo

CoOH

Ri

C00H


:Ʒ² F
291
J

;


Cld9frcre,t,ӡ




:t



l

()1( )(

::;1::: ;:

synthesis;Nicmcnto vski Quino nc synthcsis

;

Ps

Mchtyre,JC .soc,B1969,539

dc nr 4,47o9 N

R Buu-H(
F Cdlacndcr

n) PEtzne oratt oxidatbn( Ioratt o da C K E.Pfltzne G.Mofatt,J^ soc.85,3027(1963),

Md oxidation of primary and sccondary alcohols,promoted by dicyclohexylcarbodiin1idc activation of dimethyl
sulfoxide,evidenuy invlving the a1koxysulfoniun1y1idcs,which rea ange intramolcculady to generate aldehydes and
kctoncs,respecuvcly

د
R v sr
J,Trccke
J


in Ox:d oJt
voI

G.Mofatt, su1foxide-Carbodiimide and Rc1ated oxidations
(DCkkC
ssJ

7,291~s03`Ի Co .o .s

Eds

c New York,1971)pp 64;T dWcll,o R Ϧ 39,297-572` ss (1990) V LCe,

2,R L Augustine,D.

(1991)Cr Corey m Oxidation;swem Oxida on

292 I ctet Gams

Isoquino ne synthesis

A. ctet,A Gams,B

`43,2384(1910l, FOmation ofisoquinolines by cyc zation of acylated an1inomcthyl phcnyl carbinols or thcir ethers with phosphoms

pcntoxide in to1ucnc Or xylene:

H

oNR 70
R


R

ث ƪ
%
293 Pictet

ubert Reaction;lѹ organ Wa s Reaction A Pictet,A Hubcrt,B r29,1182(1896);C, Morgan,L P Walls,JC .s c1931,2447;1932,2225

2

ۮ h $
Ri

:l

Jپ ɪ ::::ٶ l Ģ

Hdcݶ
nc c

znC12

or P0Cb

+H2O

;; ȡ 1 Ʒ ѳ α V ָ
;: f

:i:

:l:f

l

v57,

294 Pictet

spe gIer Isoquino ne sy thesis

A Pictct,T spengle B r FOrlnaton of te ahydroisoquinoline deovativcs by condensation of arylethylamines w"h carbonyl mpounds ",2030(1911)
and cyc1ization ofthe schiff bascs fomed:

r\+ cHo~
295 P oty Robi son

HCl

)I( )r'i)
R



R

ڡ Ʋ : ƪ º
synthesis dc Or hydrogcn o.Piloty.B
chloIf ide:

r43,489(1910);G M Robinson,R,Robinson,JC .soc43,639(1918)

FOmation of pyrrolcs by hcating azincs of enohzable kctoncs with acid cata1ysts,usua11y zinc chlo

NXl

2 :ڥ
;:;

Ѿ
+
R2

:1 S ɪ l ? 619^641;H Pos f g
296 Pinaco

Rearrangement
9,

R Fittig,A

114,54(1860)

Acid-catalyzed Fearrangemcnt of vicinaI diols to aldehydes or kctones:

R ߵ R m
0H
am in s.Pat ,Ed,C r cϦ `14,357(1960l;C J Collins,J,R Easɽ CmIJJ,(htcrs0Cncc,New York,196 pp76 76 B.Rkbom,C mr,,Org ,3,72 732(1991).( ffe neau-Denvanov Rearangcmcnt.
Js?

RW ,|,srC J.Collins,g Ϧ R

ɳ oJ

oNR 71

ho1Tre
alcohols yields ortho cstcrs:

ment of alkylimmates with ammonia or p

ma1
ǭ R


N
H


R



R



N

ߵ

R-C N + RioH

HCl



RC(oR1)3

Ʒ
298

gn:1: J

Ʒ
t lŬ: hJ;

%

6 PL r1 fߵ
,

nner hz ne synɽ es1s

t



ߦ

Ŵ





md f
0
HN'J `NH









mm


0H

2 <

NH2

+cog2

H ^

ȴ

`

NH

HN



-NH3

N' N

N

2HN

Hg
c g2

NH2

% ^lL c ̾
NH HN



oH



0c


299 I a

ߦ

Reaction

l¶Ĵ




̯
,9,

r 1 J
s
N

m m ߵ

d

HCl

o 3

H20

0

J.R Bunnc ,R,E.zahlcr,C d د ߶ C &r,9 ( 1978,583?

R v49,398(1951);R

-We9? J11'1,457(1957);R Bud arek, schrotcr,o D

300.PblonoVski ReactEon;Potic Polonovs Reacuon
,s M polonovski,M,Polonovski,B c Chf
,

Frc c

41,1190(1927).

oNR 92

organic Name Reactions

ds



1



mF: ::I t

l s Ʒ l
i

::

:

Ͻ
H

ne

:l:l 1\;1:|


thC

R





ӡ

J


+|

; dz ; sɪ ߶ ɩ T1 % fɬ ȵ 45,2683(1989);R J.sundb ɳ 48, 277(1992)
l ;

.36

D& ʥ ɺ ) ̤ ཹߵ 1:lF{ и
n r ,jD

?

rg r J,,

301

Pbmeranz Fr" ch Reaction;sch Mtller Modi cat1on le

C,Pomeranz,Mo,In 14,116(1893);PF tsch,B r26,419(1893);E schlitucr,J.Mullc J`C Ac 31, m

914,1119(1948)
1: :a

n: fߵ θ Ʒ : Ʒ 1

%H+ߵ

J Ի

ء
oEt

H

һ % %
302

"


; :

½ ʢ : W ; I
Ponzio React:on G.POn o,C .C .Jrc127, 171(1897) Fomation of dinitrophenylmcthancs on1benzaldoximes by oxidation with nitrogcn dioxide in
ther:

2
303 Pr vost1Reactio

%

̡ح ȺƮ ƻ
C Provost,CV`mP
R 99


Ϧ s-glyco1s:

196,1129(1933),CA,27,3195(1933)



Hydroxylation of olc ns with iodine and silver benzoatc in an anhydrous solvcnt to give
l

RCH==cHR

C6H5C00Ag

Rռ H_

cHR ~ L اL_ R~::2E:ɻ R I l 0COC6H5 ocoC6H5

20 ~ R~::~ cHR | 0H
oNR 93

; ա u

)n

300 Pr ezhaev(Pr
N?

alkenes pera Tf u ɽ I :1;

esch ew)Reac

on

RHC=CHR + C6H5C02OH

o


R

+ C6HsCo0H


sOs?

t ? 1 ԩ ߵƷ J׺ ָ . 1ʶ Ⱥ ح: rƷ hols sElˡ
(li

}}

alc

oxa11u(:{sI

m Ƨ и ƪ
r


m + C

CH2

RCH0H

R
C " C l C

H H

n
0

o o

ߵ

@rg 2,52561(1991)

306

Pschorr Reac"on

R



ֺ ٴ ves ftomɽ a zed aryl oͪ hoonnam sby h͡ amolecd



J+ һ ޡ
۸
307

Pu-erer Rearrangement

l
ߵ

̡
1


r

m h ǡ

Ac9O~

د

R2




R2|




^

߹ 'sѾ cH3 Ѿ o


oNR 94

ƹ Ӥ

Ӫ

ߦ
organic Narne Reactions


0H
cڥF ;د :

0

HCI

Ag2o

oMe

H

? r& %
R
`

: 1:

: د
JF
:

1: l::l I1J

ٲ

309.QueIet Reaction

p

R.QuClet, b'

19 155(1932),

:

{

:

o M e

i

i u : J
CHRCl


RCH0+HCl

+H20

B r

Է ص :ҡ Ͻ Tҿ : { %
:

a

J

310

Ra1nberg Bݲ ckIund Reaction

`

L Rambc ,B,Bac und,A v





-halo su1foncs with strong bases to yield Reaction of

C 1sf

)

(19409CA 34,4729 94

,

һ һ ح
l

s%


311

f;25

˼ ߵ 뾽 ;:1ߡ ; ó 1 f 鱸 JƷʬ ԩ ::{;; ɻ
i;


J:ح

ifiɻ

l

::

ɽ J Ң by theߵd sdѵ mzcneڢ mduccd eѵ o :Ǧ
:
C

Raschig Phenol Process R Raschig,F pat,698,341(1930),GA.25,3012(1931).

Hs+

+ %



COHsO+߳

o-=

>COHs0H+H
ޢ:

Jog,,voI 17(New York,1982)p378
312

: F

1ѽٺ
:

Reed Reaction

`

caF ˡ ;

: alIP ɽ 1111 Ʒ mɽ mn
:::: h:%
:

RH+s02+C - L-.

Rs 2Cl+HCl

oNR 95

organic Name Reac

o s

- ,562,23(1949);H.Eckoldt, D ߶ Asingcr dԻ l,B r75,34,42,344(1942);J.H.HC1bcrgcr f J,,A 9`9, m٢ (Bcdin,1958)p201;G,sosnovsky,Fre RϦ v 407-427(1955);A sch0nberg,P V Js P o c o v c jo s PrePϦ 0 Ϧ jc CJ9 r (New York,1964)p105. c

`R
s13?


!f ::I l:

Condcnsation of aldehydes or ketones with organozin:٩

lR ss PhJ,s, 1s l ydd
l ;;

:1̨

rs

-hydr v cster

+ R r/

0

Rm ҡ
R

o

Ho

o
J i:::l ::

M

aton to thc synthcs of kcto Rm r@l,% dro r Asy롨 dm 51,z939(1995), 5,189s(1994),MCthods dcvdopmcnt for mc synthe s of 1actoncs H,schick Ի , rr, s 1989,57 590;M,W1Rathkc,P We e ,Co R vj sf A.F stne s,, .2,27 299(1991).( J,, dro L f csters:C,Kashima r l, 0 C ,58,793(1993).Asymmct c synthesis:D
elec ophilcs

1 s ּ ::IƷ lT:Chandrasckharam 1:~ R ܨ C r934,6439(1993).Appl M
Frg

Aldol Reacu n;Blaise Reaction.
314

`0

Reime Tiemann Reaction K.Rcime E cmann,Br9,824,1268,1285(1876)
FOmation of pheno c aldchydes fron1phcnols,chl0rofom and alka



m~&m
+cHc
R v fH

+sKcl
?

CV`

sI?

c Wynbcrg,C .R v6 169(1960);H,Wynbcrg,E. 1Me e C rg R Ϧ 2 2(1982);H,Wynberg, ,2,769-775(1991).( Duff RCaction;Gattcrlnann Aldehyde synthesis

315

Reissert Indole synthesis

`,o

A,Rcisse ,B r30,1030(1897).
Condensation of an o-nitrotolucnc with oxa c cster,reduC on to the a 1ine,and cyc zation to thc indolc:

Ի

T





H

W10,Kcmack rԻ l,JC ,soc119,1602(1921);R C Julian l,Jfe rocycJjc G Cannon rϦ J.,J Me C ,,238(1981)
316

Comr o ,tds3,18(1962);J.

Re sert Reaction(Grc,sheintz Fche Re sert A ehyde synthems) soc.63,2021(1941) A.Reissert,B r38,1603,3415(1905);J,M.Grosheintz,H 0.L Fischer,JA ,C Foma on of1 acy 2-cyano-1,2-dihydroquino ne dchvatives(Reissert compounds)by rcaction of acid chloHdes with quino ne and potassiun1cyanide;hydro1ysis ofthese compounds yields a1dehydes and quinaldic acid -


+

+

һ

N֭ C
|

3+RCH
c m+



COR `55,511(1955);ED ? ; ־ ɺ J1 T
Rv vv

m,R E.Mose g,o R0Ϧ c 8,220(1954);L E.McEwcn,R,L.Cobb,C

9:1

ߦ º FѪ ȼ r
carbonyIau n as developcd fron11928onward by Waltcr in Ludwigshafcn:

oNR ,6

orga ic Name Reactions

H2C=CHOR- R H HC cH_쵩__H2c=CHsR
> RRtC0+ HC CH- RR C(0H)C CH?xL~ RR c( H)c CC(0H)RR. 4HCԡCH- -oyolooctatetraene

4HC CH+ 4C2H40H+N C0)4+2HCl -
J.` 1Copenhaver,M.H



4H2G=CHC0oC2H5+NiCI2+H2

Bigelow,Ac

dK J ds(Berlin1949);H ^c
r

Kropc Jfo'ɳ - s(Ncw York,1965)p67;L,E Fiese M Fi 183, 185, 190,519,720,722,723.Rcvicw of carbonyl 'I/s
Ϧ


' J9, ~ C rrI,U.s Dept Commc c PB18852-

,ad ~J ,, CϦ

bonyls-Reppc Rcactions

243-308.Mcchanistic study of cyclooctatctracne synthe 5470(1986);C.J.Lawrie rϦ l,o Ի o JJ0cs8,227

in sy ɯo s s1 J CϦ o د

318.Retro~Dids AIder Reactio

Thennalɽ ssocia on ofI)iels-Aldcr adducts,oCCumng mostread

yvhcn one or both fragments arc particularly stablc


;; 11 8

:

+

Ѵ Ÿ z ϭ Ĭ


A Lhhan
? l9:9`
:

.

319.RetmpinacoI Rearrangement N.zelinsky,J ze k0w,B r34,3249(1901)
Conversion of an a1cohol to the rearranged olc n on treatment with acid

`

c: ߳
-H20

ή
iiJ


320

a 롹ÿ
c ethers:



{;t ;

ߦ

Reverdin Reaction
R Revcrdin,B r29,997,2505(1896) gration of iodine duHng nitraJon ofiodophcno


O R E

HNO3

ߵf :fԨ J
W l fۻ
321

: z%

j

1|

گ š } g
vith or without

Ŗ hm Quinoline synthes
P Riehm r18,2245(1885);19,1394(1886);:d ,AP9,n,z38,9(1887) Fomati n `,,B of quinoIne deovauves by prolonged hcating of arylan1ine hydpchIohdcs with kctones
usc of alu inun1chloride or phosphoms pcntachloridc

oNR

orgamIc Name Reactions

+2CH3COCH3
NH2? HCl




? ҡ 1 R G EldC d


322

۰

;:

ƪ

P

&J1 :د :;J

R McCa ʴ

Riemschneider Thiocarbamate synthesis r 64,99(1950);P Ϧ ,Z JrcJ J 89,118 4,460(1949);C j .JP, ( r د R.Rʼ mschnodc E ahn,P Ի
(l:ح
;l: }?

i n fconce m d sulmoc a d followed by tre me e-w er serves tmnsm arylɽ iocyanates

into thc co csponding thiocarbamatcs


H H
` ؼ

ArsCN



s
/



N

һ
s

C o N H

^C rs 9b,277(1952);RR mschnoder,G,od k,Mo .8 316(1953);K,schm t,P Kollcck-B0s, rsc ġ ,C soc75,6067(1953)

323

J.,J^ C ,soc,7 5905(1951);RR m~ R,R mschn dcr,C j d(M د33,483(1951);jd Ի ,64,420(1952);RR mschn der,C J˷ . dMڥ 34,353(1952); ,z schne cr,G Orlkk,A g د

Riley0 dations(seIe iuln DEoXide0 da on)

& 1 Ʒ
groups:

le um

do

he o of on

uve Ineth

enc gmups carbo

CH3CH2CH0+seO2

-CH3C0CHO+H20+se


324

1972)pp407-411

,13{ ;}l;

gfg

и

:

j

;:


1

l κ F ξ

nutter IReact:on


H3c>cH2+


J.J.Rittcr,R P Minʼ ri,JA ,C soc,70,4045(1948);J.J.Pu cr,J,Kalish, 4048. cs synthcsis of an1idcs fron1ni and alcohols or aIkcnes in strongly acidic media:

H3C

N

[

3cla- ʽ



3/NѾ

R

o

? , } : ڥ ; f :۫ , ¡ ݲ !#i % :r% % 6967(1994).
i
: 1 J 325

Robinso AnnuIa on

simplc de va vcs of methyl nyl ketonel or its Cqu~alen ,fo11owcd by an intramolccu1ar aldol condcn

Ѵ ܮ ܢ ռ :

n

byѪ

add on

y һ һ
0H3

mcthu qdohcxmonԿ
O H R



ket nC

Or

on, v:



ӭ


R



()l(()1

۸ʮ Ӱ ɺ Ԩ
action;,VichterIe Rcaction.

oNR 98

organic NaIne Reactions
326

R

Robimson sch0pf Reac
t

on
:

顾 ɻ miƷ fƾ ;θ

:i:1

ʡ ͡
1f

11 : ; %

::ʬ

30?

ǡ ŵ ұ ֡ Ͼ

327.ROse mund Reduction K. 1Rosenmund,B r51,585(1918); .l Roscnmund,R zetzsche, dy rcdu d chloodcs chyɽ %prcve m her hydrogcn m apos `54,425(1921)

+H2 -2 22 ~ RcHo+HCl

`

ded the

cata

RC0Cح


)ilح

:;l;{s

и ح
i! l||i
|ح }e|

||

328

Rosenmu d von Braun synthesis

.WR cnmunϷ E stmc B 52,l9zI9 91ClJ
Conver ion of aryl ha dcs to aromatic ni les in thc p

Ի
˿L+

iȸ PJ11C931)

ArX+CuCN-

:{; J

AcN+cuX
I

{

f1;1; J;:?

֬ ح u a %د F
;:

c{

V ɪ

a
,

));));



329

Roɽ emu d Reaction

P Ro cmund,JA .C .soc57,2010(1935);61,2912(1939)
Preparation of s(,-tc asubstitutcd porphyons by condensauon f pyFolc with an aldchyde:

H o

4R H

0

A }
330
A

~

ڬ 1 f T
1

^

;; ;:



;:

1 .C95 ,Mccha Bad :
rԻ J,,

d

Rubottom Ox:datio

G.M,Rubottom

`9J G Brook,D.M.Macrac,J@ o lC ,77,C19(1974);A,Hass1er

ɯ Ϧ ,Ter Jrt, rrers1974,4319 oxidation of enols ancs with hloropcrbenz c acid(

0

C ,40,3427(1975);

-CPBA)to arord ~hydroxy kctones:

˾ m
oNR 79

9zI

' sɻ lɪ 겵 Ʒ 3 o :9 & u hydmɯ n pem
shortcning ofthe carbon chain of sugars by thc Oxidal
i and fcrrlc salts

; 18 ll

S:Ŭ % 1:f

f f

252(

Ի G R Johnson JA ,

d14,

RCH(0H)Co0H+ H202
R s90,123(1981). 332?

Fe3+

RCH0+C02+2H20
h o

WP man,TJ9
:%

ɳ CϦ



n

٢ s(Academ

Press,New YOrk,1957)p118;Hs,Isbcll,MA.salam,C





byѴ rmal ds ѿٸ Ʒ Ʀ Ѽ s о : Ӯ



:;:
fI

9,249,3

9,3:9,499(19

.

w"hm ds decompo don of

)M :I ƥ
Ii
L.Ruzicka,C & rLo do د54,2(1935);H Gi1man,o Ϧ jc C js` - VJ0/z,754(1955) Cr:lanc Reaction. Ziegle ffo ɳ
333
vo ?

1(NCw York,1943)p78;K.

saba er senderens Reduc0ion P sabatlcr,J.B,scnderens,CV P,R 128,1173(1899),

Ʒ߱ g
d

;

)

s 9 sl;

;;I;IIl ; ; ;J;fƼ lI ;
J


F

334

sakurai Reaction(Hosomi sakurai Reaction) ߶ A Hosomi,H sakurai, f Jm L rrers1976,1295;A.Hosomi Ի ,C
Lc vis acid-promotcd nuclcophniC addition of a11y

L r٢ rs1976,941.

c silanes to carbon clcctroph es accompanied by rcgiospeciflc

transposition of thc a11ylic moiety:

lHBCl

ұ

Ӯ


des,acetaIs,ketals,e oxides,iminiunl sa"s

E aldehydes,ketones,enones,acid ChIo

Lewis acid=TiC14,AIC13,BF3? o(CH2CH3)2,snc14,(CH3CH2)2AICl,cat CH )3sios02CF3

I  Ʋ ѥ i
o ĵjc co
ds Vol

3,I Bemal,Ed(E cv NC

593(1991)

`

carbon disuliide:

lCsH

HlaCs

C6H6NH

=NC6HslcN ҵ ~c6H5NH =NC6HslCsNH2

ڢ
~
H



oNR 80

.#׫ ɬ ߨ
cycJIc b` Po ds3,207(1952);o etanilidc Isatin synthcsis.

Baye

Eckc , ɳ ~NJ7'4,11(1968),QC

sandmeyer IsoniLOsoac-

336

sandmeyer Isonitrosoacetan ide Isatin synthesis T sandmeye Jie`vC ,Ac 2,234(1919). m n of os c odphen ٳ dne by
clization with conccntratcd sulfuHc acid,and quantitativ|

con:
sFJ: 1 l:ح
lI

aٳ C and h
i:Ildmx߶

ӭ 5 ߸ `N
(( l

Nc6߸
H



塣 ڢ
~
H

cyL



觱 ط ̡ ȣ ح
337

sandmeyer ReacJon;Gattermann Reaon;Korne Contardi Reaction sandmeye B r17,1633,2650(1884);L GatterIn nn, r23,1218(1890);G,K0rncr,A,Contardi,^ zl Lj c j23I 464(1914),GA,9,1478(1915)

fj Acc



Ԩ

: : ˼ :
C6H5Nۻ X

1::1

fϾ ڥ :lh
:

~.~ c6H5Cl -L2


338

sarett oxidatio ;Co ins OxidaJon

sarett, CJ, PPJ s c,75,422(1953) oxidauon of p mary and sccondary alcohols to aldehydes(and/or carboxy c acids)and kCtones by means of CK ^ py dine complex:

G.I.Poos,G E,A h,R E Beyler,LH

-

)C= ʡ Pc η amin,Mcnlo Park,C hfomia,2nd cd.,197 ,}: θ I s(W1A.Be , : ǭ pp26 : R CR d Mcchanistic smɽ
)C(:H
:

j

~~:;?1: l; 9s:i
273

sV





Hasan,J

ROcek,`^Ť

CJ,

.soc97,1444,3762(1975).

̼
339

Ĭ
BF4

$i


~
r

cs

;;!

schiemann Reaction(BaIz schiemann Reaction) G.Balz,G schicnnann,B r60,1186(1927).

FOrm ion of diazonium nu r borates by diazotizݶ ion of arom amines in thc presencc of nu lowed by th rthema1decompo tion to aryl nuoodes:

borates,fo

ArNH2+HN02+HBF4

ArN

ArF+N2+:F3

ɺ f Ȱ ? rael,JP .321,579(1979)
sa.;};;}:
)

C

? η θ
oNR 81

`

organiC Na ne Reactions
340

schmidt ReaCtion

a
RCo0H
R C H


s

T ٦

H 2 s



1 Ѿ Fm

RNH2

RCN+RNHCHO
RC NHR

RC0R
R

o H2s 4

4

0oH H2s 4^ R2C=NR
R
,ors Part1,P de rrg g 6);PA.s.smith in Mo c߶ JԻ rR

R2C=CR2 H2so4^R2CHqTNR

T h %
JA .C
soc

Ի z3(1992);J. YM rour l,J rocycJ C .31,87
)16(1994) R T shioi ,ComI,,o sy 6,817-821 r ;emcnt;liofmann Reaction;Losscn Rca angcmcnt.
341

Ʒ

115,10183(1993).ExtCn

on to didkyl

scho

.394,111(1912)| R scholl,C.seer.A
Coupling of aromatic molcculcs by catment wiɽ Lcwis aod catalysts

ReaCJon

H

Ar-



+H2

% )pp

1 ̰ Ʒ

(f
:



fl:f


,


:E{:i%ǭ

ѥ
ߵ ߳ ߳

H

r
R=H,CH3

߸
Hi

i(ح
`

ߵ
o

flcHO

+L V oCHo

E=alky|ha"des,aIdehydes,ketones,thioketones,acid chlorides,epoxides,ac

lates

j
oNR s2





organiC Nanne Reactions
343 schotten

Baumann Reac on
ne solution:

C schotten,B r17,2544(1884);E.Baumann,jɳ j 19,3218(1886).
Acylation of alcohols or an1ines with acid chlorides in aqueous alka

ROH + Yx - o
R fN,0,V

Na0H~~ R

R
1'

o

`52,272-273(I953)syn rs4,335(1994). soc Jgp 42,1756(1969);G I Georg,Bjoo are c ,Lef
344

sonntag,C/,

R

etic appl ions:M

Tsuchiya


l,B Jl C

.

semmler AromaJzation,WoIfFAromatization) semmle Wolr Reactio (Wol 1semmler,B r25,3352(1892);L Wol A ,9322,351(1902) nsaturated cyclohoxenyl keto mesinto aromatic amines under aodc Rearrangcmcnt of ,

nditions:

NOH

H3C

CH3

dc߳
c J֮ zr fIf ɯ Jo s Vol

c s R wJ R,1I1Conley,s.Ghosh inد Ϧ so/Mo science,New York,1971)p251;M.I El-shcikh,JM.Cook,
f

B.s ThyagaraJan,Ed,lIntC 0 ,C 45,2585(1980);Y Tamura r J,,sy ١ ˷

sjs1980,483.
345

se ni ReacJo A.serini J,,B r72,391(1939) ` zinc-promotcd rca angcment of17-hydroxy-20-acctoxysterol dcnvatives into C-20k able to other cyc c,as we as opcn-chain alcohols:



tones;the rcaction is app c-

Zn~


R v C W1shoppe,C j J 4,418(1948);L,E Fiescr,M,Fieser,s s(Ronhold Pub shing Corp,New 9 YOfk,1959)p628;N.L Wendlerin MoJ c rR ԻrrgѼ P9 Pa 2,P dc Mayo,Ed eyJnterscience,New YOrk,1964)p1038;E.Ghera,C ,C 9a .1968,163 0 C ,,9.35,660(1970). 346

sharpIess Dihydroxy atio

EN.Jacobsen J,,JA .soc 110,1968(1988) C ߶
osn1ium-catalyzed asymme
ic c s-dihydroxylation
D . o
m

of ole ns:

i x .

o H



Rf ';



:
|

/RM +h


RL H

ls


M

H

H0



oH

AD m "0 0H" A premix ofthe fourreagent oomponenls is commerciaI ava"able The compos"i n Contalning(DHOD PHALis termed AD mix mpos on oontain ng(DHQ)2 PHAListermed AD mix ;the (DHQD)2 PHAL=1,4 bisl9 0 dihydroquinidine)phthaIa ne;(DHQ)2 PHAL=1,4 bis( 0 dihydroquininelphthalazine

RL=largest sVbst"uen1RM=medum lzed subst"uen1Rs=sma"est subst"uent
No` r Thc schemc shown is an cmpiHcal rnnemonic indicating olefln oHcntation and face selectivity.Itis not to bc

considered an absolutc predictor of ncw dio1conflgurations.

A11yl and vinyl s anes as substratcs: A R Bassindalc
dihydroxylation of a polycne
:{ I:

s.C.sinha,E Keinan,J@


;

::::; :

I 1994, 1061. Chemoselecuve s. ` @l, FV C .59,949(1994),R vj R.A.Johnson,K B. s g s 1د f 1% ~ 1p : ڬ : T;
8

oNR Bs


stereoChcmistry
D ( -diethyI

|





ta"rate(unnatural)

:0:


70-90o/ yields,

":O: "
L (+)-dleth

)90%ee

ta"rate lnaturao

No Thc asteosk at a chiral centcr denotcs a prcpondcrance of eithcr thc R Or s confIguration. r Mechani studies:s.s.Woodward r l, A C :st,c11 106(1991);M.G,Finn,KB.sh

ߨ
Ⱥ

.

մBt; Ө
dC$,jD
} |حi|

}i|!ح

C9J

C 164,63-77(1993).

h

: qϳ hm m m mֺ m utcd

olѪ

d

vicinal an no or an1ido alcohols

2
(CH3C"2)4NOCoCH ,cat0s04
R

=C(CHslo,1adamanlyl

R4=CH2CH3,C(CHsl3,CH2Ph

R5=R3,Ts,C

R4

Ƨ % ھ Я շ
New York,1986)pp642-645
349 sin mons smith

J ,0߶

ڼ ƾ ǯ RH.I deF Press, Jongc,Eds.lPlCnum ,WJ,M
s,C?

C ,soc,80,5323(1958). HE,simmons,R,D smith,JA

Reac on

stereospeci c synthcsis of cyclopropanes by treatmcnt of olc

ns with:neɽ ylcne iodide and zinc coppcr couplc


R vj

+c 2+ c lCaH
R c

0~X+

+

Rat r l, jd179;A .46,2751(1981). `Ϧ
350

sJH E.simmons r J,o
scle r

.R 20,1(1973);C.Gkd,JM.Conia,J Ch s,(sد 1978,18 W1

C J ,Ac

62,866(1979);J.Joska,J.F kos,CoJJ,Cz

c C

.Co -

`,,ffe

simo nI Reac on

1% ɽ s 1 l
t

salt of a carbo

c d 0d



2RC00Ag+I2 һ RCOon+2AgI+c02
oNR tBz|

organic Na1ne Reactions

H Wie1and,RG.Fische
ham, Dj

A,9

,446,49(1926);J KlCinbcrg,C



R v40,381(1947);R,G,Johnson,R.K

Ing-

c ,JC ,54,2612 ߶ 56,259(1956);C VV lson,o .R Ϧ 9,332(1957);NJ.Bunce,M Hadley,C

(1976)CF HunsdiCcker Reaction.
351

si1nonis Chromone Cyc zation E Pctschek,H.simonis,B r46,2014(1913) FOrmation of chromones from phcnol and keto Csters in the prc$ncc of phosphoms pento de,phosphoms ox
chloHdc Or sulfuric acid C umaHns Fnay also fonn(Pcchmann condcnsation,-9


R wsf



+RCHac cHp



P9 s

'%s
(() I(

):

H+HP

O
s.M.sethna,N.M,shah,C .R

i

`36,14(1945);s.M.sCthna,R.Phadke,0 J CJa hng,Am 605,158(1957);s.R Tan,A9rsr N,Lacey,J Cr9 .s c.1954,854;o.Dann,G ,25,1367
(1972)
352

R c 7,15(1953);R,

skraup Reaction

zH.skraup,B r13,2086(1880)
synthesis of quinolin s from aromatic an1ines,glyqcro1an oxidizing N H
c
C l C

agent and sulfuric acid

H 2 o

H O H

2 O H


1935,181;1936,329
1igration of an aromatic sys-

R cr7,80-99(1953).G M.Badger J,A s JC 16,814, Early rcview:RH,R Manske,M.Kulka,oѼ Ի Ի 828(1963);M.Wahren,Te d20,2773(1964);EB.Mu11ock l,JC ,so C1970,829;N R Buu-Hoi

Ϧ J,,FVrrcP,s 1972,260,263Cf Bischle Napieralski Reaction
353

smiIes Rearrangeme t;Tmcc-s liles Rearrangcmcnt

A,A Lcvi Ch .soc.1931,3264;å`J,Evans,s.snilcs,`Dj ,J

Intramolecular nucleophilic aromatic substitution in alkahne soluJon rcsulting in the
also bc a phatic:

tcm from one heteroatom to anothe The two-carbon unitjoning X andY is usually part of an aromatic hng but may

z

C
2228(1968).



x

n

i) C

[; t :

h% R,9oNHR

m arrangement: L E Tmce I,JA .C

Thc convcrsion of o-methyldiaryl sulfones to t,-bcnzylbenzenesul nic acids is rcfcrrcd to as thc Truce smiIes re s c8 3625(1958);G R Crowther,C.R.Hausc Jo C e .33,

d ?R
354

0H3

1
: { |

R

cR rro g ߶ rs(Else e E re Cws:J.R Bunnett,R E zahle C ,R v4%362(1951);H,J,sh ne,A,omϦ c NewYork,1967)pp30731 V`E.Tmce ,Org.R Ϧ 18,99-215(1970),ConvCrson of phenols to aniline IGC

Coutts,M,R,southcott,n%t Trc sr1990,767,Kinctic study: .BOwdcn,PR. 111hms, rrd s. 1991,215, n ) thc sy Mcm ds devcl mc ٤ ˧ h substrate M.sako pi;|;i;ح l,P % . : ح thesis ofphcnotlf jiazhc s K Mukh cc Ϧ
sommelet auser IRearrangement
alka rnetal alnldes:

d205,56(1937) M sommclct,Comr R
Rcarrangcmcnt of benzy1quatemary ammonium salts to orrho substituted benzyldalkylamines on treatment with


oNR B5

organic Name Reactions

~J)!!I!

,~
~ I

)''''CH9NlC áá á

áá áá áá

N

أ :1 :
substitution:T,Tanaka
a angemcnt,G`):T
rϦ J,, j

40,518(1992) selectivity studics(sommClC Hauscr rcarrangcmcnt vs stcvcns rcrr, sf1992,2851;T

J,د Kitano Ի %rt0

Tanaka
`,,JC,rg,C

,57,5034(1992),

Mosenhomer Rearrangcmcnts;[2,3]- Ittig Rearrangcment.
355

sommeIet Reaction M sommclet, b`

.soc C Frc c [4]23,95(1918). ж R 157,852(1913);B Prcparaton of ddchydes from aralkyl hal es by trc ment with hcxamethylcnete amine to y ld the quaternary `
ȴC X+%h

salt,fol1o ved by n1ild hydrolysis

һ

߳

Co߳ ڢ



uc|:1:

I;F ¡ Kr0hnke Oxidation
:
\





!9J: : 9

l

:;;

%ѿ :i:;I%,

c}

ح
l :{ ,

r

356 sonn

1t er

lѹ ethod
1le B

A sonn,E.M

r52,1927(1919)

Rcacu n sequenCc c ployed to convcrt aromaJc ani1idcs to aldchydes Treat:nent of the an ide with phosphoms pentachloode generatcs thc iѪ doyl chlohdc,which is rcduccd to thc imine with a xture of stannous chlo de and hydrochlonc acid subscqucnt hydrolysis yiclds the aldehyde

ArCONHPh - ~> Ar =NPh һƹһ AcH=NPh - اL9 ArcHo
Cl

Ac 1s,1105(1932);W1E Bachmann,JA C .soc.57,1381 T Rochsteh,H zschokkc,Fѫ J`Ch9 R 8, (1935);Ts.Work, C ,soc.19,429;L N Ferguson,CJ9 R c `38,244(1946);E MosCttig,o jc c s ߡ (NeW York,1961)p832 Gmndmann Aldchydc c 240(1954);L R Fiese M Fiese A v d@
synthesis;stephen Aldehydc synthesis
357

staudinger Reaction
H

r staudngcr.J Meye J @ m Ac 2,635(1919), synɽ esis of phosphazo compounds by thc rcaction oftertiary phosphines with organic azides:

R3P+NOX

>RaP=N^N

N^X



- R:P=N~x

ph sphazide

R J

Ϧ G Golo1obov J,%' J 37,437(1981)

358

l f mc l uc Ţ Ʒذ Ʒ ma ߱ d mnous
stephen Aldehyde synthesis
t

chloHdc and hydrochlooc acid yields the in1inc s31t complcx which is subsequendy hydrolyzcd to thc aldchydc.Practica11y apphcd only to aromatic aldehydes

s

R c N
C

n
~ H C

2

(RCH=NH? HC)2snClo



H20

RcHO

Ǯ ⳾ ð
oNR B6

ߦ ա

organic Nanle Reactions
359

T s stevens rϦ I,JC .st,G1928,3193;1930,2107,2119;1932,55,1926,1932 n ana cѴ ca a oѴ m : : Ӫ t:t 1 Ӫ ּ Ʒ sע 1R1 : f: ߵ

stevens Rearrangement


R3
|

NH2-

R2_
:

Y'

NR ors

˷ fv(Academ Press,New York,1965)pp223d York,1963)pp34 406;D,J Cram,F fs CԻ Իjo C ity smɽ es(stel/ens rearrangement vs sommelet-Hauser rec 22 s,M Pine,@rg.R 1 403-464(1970,sele wfI l,FV TrnP,sr1992,2851;T Tanaka rϦ l,J Org.C .57,5034(1992)R v arrangcmcnt, Tx tan0 t E.M̪ 6, nr ,o1 s 3,913-932(1991). M n mcr Rearrangements;[1,2]j Rearrangcmem
)

E

r('

iCws:H

E

oɽ c mmcrInan in J rR rrc g rs e

1,P de Mayo,Ed( e Intcrscience,New

360 st g tz

soc 36,272(1914) J,sticglitz,RN Lccch,B r46,2147(1913);JA C Rea angement of trityl hydroxylan1incs to schiff bases on trcatment with phosphoms pentachloHdc

Rearrangement

AraCNH0H

ا L~.

A%c=NAr+POCb+2HCI

rn ,9z rs Part l,P de Mayo,Ed OViley-Interscience,New York,1963) R vJ ,,sfP A.s.smith in j @` c rR Ի 8 p479;r/ yAcԻ sci31,504(1969l;N,Koga,J R Ansclmc, r d J f٢ rs1969,4773;R V Hoffman, s ж D J Poelkcr,Jo C 4 2364(1979),

361 st Ie

M Kosugi

b



Coup ng ߶ r l,C ,L rrers1977,301(1977);D M stCin,J, ,stille,J^߶ C .soc.100,3636(1978), o Ѫ n ɽ acctat or pcm atcd s

mdm
X

s








һ

R3sn Ri+ߵ

Ri~

+ RasnX

Pdl=Pd(PPh3)4,PhCH2Pd(PPh3)2CI
R1=alkynyl,aIkenyl,aryl,a"yI,benzyl,aIkyl

R2=acyI,alkeny1a yl,benzyl,aryI X CI,Br,I,oC0CH3,0SO2(CnF2n+1),n=o,1,4

ح ˢ 1
wsJ K,stillc,A kett,J,A.E man, A C .soc.117,3306(1995).R
g ߳ C . r,E 25,508-524 (1986);M Pereyre Ի , 0 Ϧ sy rJ9 s(Butterworths,Boston,1987)pp185-207pϦ sJ Re ew ofsyn s ɽ et appli tions T N Mitche11,sv 1992,803-815,Cf Heck Reaction;suzuki Couplhg.

362

stobbe CondensaJon
H,stobbe,B r26,2312(1893);A99m 282,280(1894).
Condcnsation of aldchydes or kctoncs with diethyl succinate in thc prcscncc of a strong basc to fom monocstcrs of

lkyl ene(or arylmcnc)succin ac s:
o

m Ph+ Ѿ
0

m ߸ ? ˡ :
H

0

oNR s7


R vj sr 1s

Organ1c Name ReacJons
Johnson,G.H.Daub,@n
1

:hf ѡ 1 ;è ɻ د Ѿ : Ŭ J دb f 좳 Ʊ &: sq ɽ ed
R Իc

6,1(1951);H o HOu
.

,Mr,d r99ksl, rjc

R Իc jo so

A Ben~

I by cyc1iza on of the resultihg an1ides with alun1inun chloride:

w?


(1;:1
364

())`NH + :|
:

һ
^


R R o

R

̶ܳ
I

:

R

g ڥ f ٲ J;:{о

11Jm

,209 :cӡ ο ;
3

stork Enamine Reaction

t78,5128(1956), C99 soc76,2029(1954);G stork,H Landcsman, G stork fϦ -acyl carbonyl compounds from enamhcs and alkyl or acyl halides -alkyl or `.,JA˷ synthesis of



׹

ӭ

R

ڥ l Ť : ѳ ⳶ƪ Ӱ
;
:I

:

38,1975(1982) r d

365?

ǭ V: :11,349(1 54)
IT

1has f и { been cxtended to include pri nary and secondary an
0
R' `H

nes

NH4Cl

R'l


N
NHR

R'l:


H

o R H
R ws;J.P
ʬ

NHR

|R

cN
Acjds Vol

R

c H

Greenstcin,M.Winitz,C

js` AP,a o
9

1 F
oNR s8

P ;Reaction1 650` ssJP,a(1994)Cr Bucherer~Bcrgs

3(New York,1961)pp698 00;G C Bar-

organic Name Reactions
366

strecker Degradation
A,strecke A .123,363(1862).

ŭ J Ӯ ͦ nr F 1 r
^ '
H



cH

N



NH2

H c c߳ cH + + Ѿ NH


ߦɪ ̡ ͮiԨkŴ
367

strecker suI te Alkylation A,strecker,A 148,90(1868)

Fomaton of akyl sulfonates by rca ion of alkyl haldes with alkali or ammo um sulfltcs
the presence ofiodidc:

aqueous

solution in

RX+M2so3

L->Rso3M+MX

{; :; 368

ڮ: :ʢ

9(19 s

;: ;4

ҥ P˷ ׾

suzuki Coup ng

N

yaura rϦ J,2Vrʯ rJers1979,3437;N,Miyaura,A suzuki,Ch rm Co 1 9roa.1979,866 d Pal1adium cataIyzed cross couphng of organic ha dcs or pernuo nated sulfohates with organoboron dcrivativcs proceeding with high stcrco-and rcgiosclcctivity:
ӡһ

BY2+ R2

X



_

B 2=B(oR)2,g

BBN,B(cHCH3CH(CH3)2)2

X=I,Br,CI,os02(CnF2n+1),n=0,1,4
R1=aryح ,aIkenyح ,alkyI R2=aryl,aIkenyI,aIkynyl,benzyI,a"yl,aIkyI

Pdl=Pd(PPh )4,Pd dppf)CI2

base=Na2C03,NaOCH2CH3,Tl0H,N CH2CH3)3,K3Po4
Compctition with Heck rcaction,g.`,whcn using an alkcnyl boronate estcr

34,3599(1993)AltCmat c palladum catalysts:G.Marck Ϧ

Ρ ƭ~%%q:8? Ԧ
~B J 24,309(1892)

`,

:: :J:(

R Y ح 2 ߴ Ma ߳ mc

A,R.Hunt dv rre's ` `,1%r 35,3277(1994);TI.Wallow,BM.Novak,J
n Ac

369

swarts Reaction R swarts,B

Fluohnation of organ polyha des with an mony t nuoHde( r zinc and mcrcury uoridcs)in thC presence of a `l^cϦ
trace of a pcntavalent antimony salt:

CIHC=CgcHc +sbF3

sbC1~ cHc=Cgc%+sbC1
Fr C rJ

A,L Henne,o R Ϧ 2,49(194Z+l;M,Hudl ky,C js`v 0Ѽ I9c c York,1962)pp93-98
370



(MacM an,New

`o

swern Oxidat n(l om t~swem Oxidation) omura,D swem, r dv 34,1651(1978)

ҫ ɾ
o H



(C0Cl)2

f

ߡ º


oNR|89

organk Name Reac o s
49,788(198oR vj A J.Mancuso,D sf Rcactivity/selectivity studics:M Marx,T dwcll,Jo C c ssJ د T dwcll,0 R 39,297572r Ի ssJ (1990) Corcy Kim Oxid ton;Pn nc M ffatt0 dation.
swem, sjs1981,165-185`
371

TafeI1Rearrangement
J.Tafel,H,Hahl,B r40,3312(1907). Rea angcment of thc carbon skeleton of substituted acctoacctic esters to hydrocarbons with thc samc number of
carbon atoms by electrolytic rcduction at a lcad cathode in alcoho
c sulfuric acid:
(n rmao

CH3CH2CRRiCH3

CHOCo

ߵ

5
cHacH9c m
lrearran

fs`v J.Tafel,W Jurgcn,B r4z2548(1909);J.Tafel,JDjd45,437(1912);C.J.Brockman,E crrt,vrgϦ c CJ, (New York,1926)p321;H.stenzl,E Fichtcr, ѫ C J ,Ac 17,669(1934);19,392(1936);20,846(1937);R Jv - A nge H H,lrogcl, ɳ yI s/1a,280,471(1970),
372

ethyIena on) Tebbe OIe na on( Ϧ EN,Tcbbe r J,,JAm C soc,11l1l,3611(1978);s.H,Pine J,, 102,3270(1980), Exchange ofthe oxygcn aton1of a Carbonyl functi nf rthe lnethylene group ofthe proposcd t
plCx(thC Tebbe rcagcnt)to yield terlninal alkcnes: 1

aniun1carbcne com

0
Cp\





a

~lcpaT c



һ

R̿ Y

Ϧ s JK.A Brown-Wensley Comparative study wiɽ ,ttig reacton, s.H.Rnc J,,sy 1991,165.R á Ar,pJ,C rϦ ,P .55,1733 744(1983);s.E.KClly,Comf,,C, sJ? 743-746(1991);s H Pine,Org.R Ի c 43,1-91(1993),CF PCtCrson Reaction,
373

ThieIe Reac on(Thiele nter Aceto uaJon) J.Thiele,B r31,1247(1898)

Fomation oft acctoxy aromatic compounds byɽ c rcacuon of quin nes with acctic anhydodc catalyzed by sulfuHc acid or boron th uoHde:

+zlCHOCOl


ɡꢲ - ˿ ѡ

--






O
R Ϧ c

oCoCH3
1%199(1972)J,M,Blatc y @ ,n nrrc sr1972,228 , rs l9,9,m7.cr nsbcrg su1fonc synmcsis
A 504,94(1933).
incs
J

W McOnie,s.A,sdch, 1994, 4;M, ratna,s.Ito,Cn
374

R v Wr J,R

l

McOm ,J.N.Blatc y,o

Thorpe Reaction

Y H,Baron,EG,P Rc R Thorpc,JC .soc85,1726(190z );K. eg1er Ϧ
Basc-catalyzcd sclf-condcnsation of nitrilcs to yield inincs which tautomenzc to cna

J

|



CH-C

|

| N+

CH-C N

+ vԻ ~ FN
{

CN

H? CNH2

| R^CN

һ C 0 ܨ
oNR 90

CN




R vJ sf

Organic Name Reactions
c J,P schacfcr,J J.Bloom eld,o .R

zicglcr Mcthod
375

`jc R (W1Be amin,MCnlo Park,Califor a,2nd ed.,1972)p742;E,C.Taylo A McKillop,C js`,0fE,,Ϧ ɬп J .o C 7,1(1970) rr s do-^ o JrrjJ sN`ley-Interscience,N, ,1970)pp1-58; Ϧ ,AdI,Ի ˷

15,1(1967);Ho.House,^r

d r,t sI,

Ϧ crj s

Tiemann Rearrangememt R Ticmann,B r24,4162(1891)
Rcarrangement of an1ide oximes(ava able fron1nit les and hydroxyla 1inc)to monosubstituted ureas by treatment with benzcncsulfonyl chlo dc and water Ѻ 6





cGHsso9C~R

R -:-Ԩ 2

Plapingc

mann Reaangement
376

r P co15,103(1953);R.R RA.s.smith,o R 3,366(194 ;M. 1P dgc,H,A,TumeL J P Ϧ .P Ի c 00,Owcns,Jo C .21,1186(1956);J.Garapon rϦ J, rrers1970,4905 Bcckm d

Tireneau~De anov Rearrangement
M fcncau rϦ J,Cb` R

20s,54(1937)
Cycl a t,

Rcarrangcment of anuno alcoho1s upon diazot aton with ni͡ ous aod to g~c carbonyl compounds `
ng hols yield cxpanded or conracted products

0
J

Covcncy,Comr o sy 3,78 782(1991)ګ 1EP ham,Cs:Rooscvclt,Jo C .37,1975(1972);D.Fat tori rϦ , r d 49,1649(1993)( Den anov Rea angement nacol RCarrangement
L.Claisen,B r20,646(1887);V Tishchenko,JR߶

R cr11,15 188(1960l;H.Metzger, RevJí PA s.smith,D.R,Bae @١ Ի

o D

Wɴ J10/0,233(1968);D,

377.Tishchenko ReaCJon
ss P s.C .s
c

38,355,482,540,547(1906);C

,mZ

1906II,1309,1552,1555,1556
Fomation of csters from aldehydes by an oxidation-reduc alkoxkʼ s:

`

on process in the presencc of aluminum or sodium

2RCHO

AK

C2Hsl3 ~ Rc

cH2R

mm,Org.s,m.co1I? voI I,104(1941 Y Ogata,A,Kawas , r d 25,929,2845(1969 o.Kal-WF ,A ,1999,1591 R JL.C hon,lV: C .20, 38,1433(1973);G.Fouquet PR st0pp,J0rg.C 641,783(1966),G^ 66,54672b,94408b(1967) Cr CannizzarO RcaCtion;Meerwein Ponndor Vcr1cy Rcduction
378

Traube Pudne synthes W1Traubc,B

Prcparation'33,1371,3035(1900) of4,5-diaminopyHn dines by introductlon of the a uno group into the5-position of4-an1ino-6-hydroxy- or4,6-dian1inopyHrnidincs by nitrosa on and ammonium sulfldc reduction, fol1owed by ring closurc with
forlnic acid or chlorocarbonic cstcr

9 N߳
H

һ L
H

22a.~~H ӭ

I

> cH



ح ; ,R v

cѫ J.H Dav son,Z ߷
P APPJ
379

sI(New York,1955)p131;A.R.KatHtzky,g Ϧ R lCy,New P rj s( û

C ,1 178(1961);J.H.Listc ^c

York,1971)pp3 90,`10,397(195

Tmst AllyIation(Ts"i Tt Reac on) dr0 rreri,1965,438 B,M Tr0 ,TJ,Fulle on,JAɬ J.Ts i ,
` Pa1ladium-catalyzed allylation of nucleophnes pr cleoph e,and substitucnts on the substrate:

C soc.95,292(1973). ceeding in an sN2or sN21fashion depcnding on thc catalyst,nu-

oNR 91

organic Name ReaCtions

~xǭ
NuH=mabnates, ketones, keto
esters,

~
nammes, ket sulfones.u sulfones

X=Br`C1.0C00R,s02R,0C0R,0C0NR2,0P0(0Rlp,N02
? Pd] =pd(PPh8)4,Pd2(dba CHCl ,+PPh3,Pd(0C H )2+PPho Base=NaH,"n o ssa

mim ons under neutral condu ns:J.Ts i Ϧ ,J Org,C 50,1523(1985)Appl ݶion to the scope and synthesis of polyprcn ds:E Konan,D Ercn,P ApPl C ,CO,89(1988),RCvicw of in amolccular app1ic

Jons:BM,Tro 1122(1992)
380

,A'`C

s r230,463

478(1992)R

;C,G.Frost rԻ l, rm dr0 rA v3,1089-

Tschemliac Einhom

Reacon

J.TschCmiac,Gen pat.134,979;A.Einoom ɯ J,,A,I 343,207(1905);361,113(1908). Introduction ofthe amidomcJlyl group into aromatic Hngs or actiVated methylcnc groups in the prcsencc of sulfu c
acid

RCONHCH20H +



C[] -



RCONHCH

L rrers1976,3795 381

R s;R schrotc Jir0 ɳ -We9,J11`1,795(1957);HCllman A g C 69,463(1957);H E,zaugg, B, hHin,@ 8.R 14,52(1965).C.D,Nenitzescu,I,G.Dinules u,R vC c 2,47(1954),GA.50,15HzI5b(1956); 34,11,14(1969);K.B tt,B r1 ,2513(1973);A.R Mitchcll Ϧ H E,zaugg J,,Jo C J,, t dro

IWitChe Pr ess pats.365 22;385,074 E Twitchc11,us pats.601,603;628,503(1898);Ge Commcrcial proccss for sp tting fats to glyccrol and fatty acids by heating thc sulfu c-aCid-washed fat20 48hours in an open tank wiɽ steam in a mixmre of2 50%wate o5%sulfu c ac and0.7 1.25%Twi hell reagent(slIlfonated pctrolcum products):

HoOCR +3H2O CH2O0CR
l

H20OCR

+

CHOH +3RCooH CH20H
l

H2OH

í ˫ ; s` ls : Ʒ (Wiley-Interscicncc,Ncw York,4th ed,1975)p431.
19zIsl p66 C,

E,Twitchell,J^ .C .soc.2 22(19 l);2 196(1906);J,W Lawoc,CJy vJ CϦcoJs(New YOrk, d 1928)p32;R.B.Tmslc J@ &Fhr f,a 8,141(193D;A.R Ba ey, d9Js rJϦ J OjJ Fnr Prod crs(New York, d 1982(1949);L.Lascaray,JA .ojJ C jsfs

M sd,HD.

soc,2

1 f ; ;ح

382

U Reactio (Fou Component Condensation,4CC) I.Uϻ ,A gϸ 1C J,I E 1,8(1962) The -addition of an i 1inium ion and the co ugatC basc of a carboxyhc acid to an isocyanide,follc,wed by spontathe ac1d component

-an1inocarboxan1ide deovatiyc Carbonyl compounds and a -adductto yieId an ncOus rearrangemcnt ofthc 1incs,or thcir condensation products,serve as preCursors to the ininium ion,Thc naturc of the product dcpcnds pHrnanly on



һ

P

_
l ح

N
P



NH2+RQ'k

H+a

~Ro_

`
< \

/ N

\

n
'


H /



L



L

һ ・
R2 0

Whcn four dscrete reactants arc u$d,thc rcacton is oRen refcred to asɽ e fou componcnt condensaton zICC). s H.Kunz rϦ J,sy 1991,103 M Goebel,IUҪ ,JD 1095.R Diastereosclcctivc methods deVelopmcn d sc ,C .00, 13(1991);I Ugi r,c P Org,syn, 1083-1109(1991), Vj sr I.Ugi,P c,Esro е
^CϦ
383

Ullmann Reaction E Ullmann,^,a,z,332,38(1904);R Ullmann,P sponage1,B r38,2211(1905).
Coppcr-mediated coup ng of aryl ha des Biaryl ether synthesis is sin1ilarly accomp1ished with ary1ha
phenols:

dcs and

oNR 92

organiC Name Reactio

s

2 (

á I ڢ
-

(

-

(

+Cula

]

)

(1974);PE.Fanta,sy s1974,9;M E cmmelhack Ϧ J,JA s Cb P0rg.s9 ,3, 9-sO7(1991), Glaser cc,uplhg
384

ɬ.R PE.Fanta,C R v3B,139(1946);64,613(1964);A,A.Moroz,M.s shvartsberg,R߶ ss C `43,679 C soc,103,6460(1981);D.W1Knight,

Urech Cyanohyd n1 ethod;Ultee CyanohydHn~Iethod Trc`C %28,1(1909). .16zB,225(1872);A J UItec,R R Urcch,^ Cyanohyd n forn1ation by addition of alka cyanide to the carbonyl group in the presence of aCc c acid(Urech
c

mcthod)or by rcaction ofthc carbonyl compound
(Ultee cyanohydrin Incthod)

vith anhydrous hydrogcn cyanide in the presencc of a basic catalyst

RRiCO+KCN+CH3CO0H
RR1Co+HCN
A J Ultcc,B

RRtC(0H)CN+CH3CoO + RR1C(OH)CN
C .soc.

`39,1856(1906);R 1928,2629;H R Dittma us pat,2,101,823(1937);V Migrdichian,z

c rrc C j .28,248,257(1909);K,N,WCkh,G.R.Clemo,


385

If ,

ߵ z11 :
::

;^11 i

{:ߵ ;



: 11

: 1:1:: Ⱥ :Jܮ Ϸ

PmJ C

of0

Jc C,,o og

C0 -

RE

Urech IEydanto:n synthesis R Urcch,^ .165,99(1873) -anino acids by treatment with potassiun1cyanatc in aqueous solution and hcating Fomation of hydantoins from ɽe salt of thc intcmcdiate hydantoic acid with25%hydrochloHc acid

R
H
'

R

NH2

K cN ~

H



` r O
H N


H C

R
H 2 o

N H

~
o



0

?

B oc

,/,soc 35,780(1913);V J BOyd,W Robson, H,D,Dakin,A .C . 44,48(1910);TB.Johnson, A .C .J29,542,546,2256(1935);E.Ware,CJ9 ˷R v46,407(1950);M.sainsbury,R s.Thcobald,RoJ'

C js C o ComJ,o߶
386 ViIsmeier

IVC,185(1986)

aack Reaction 1ides and phosphoms oxy-

A.Vilsmeic A Haack,B `60,119(1927). Fomylation of activatcd aromatic or h0tcrocyc c compounds with disubstitutcd foma chloHdc: N(CHsl2

c mO+POCaһ

ح

2

=Cܳ

l+0

d CH0


(1981);C Jutz,A a 0rg C .9,225-342(1976);o.Meth-Cohn,s.P stanforth,C
(1991)
387

R v lI,sr M.R

m.FrnPac 1962,1989;` G,Jackson dc Mahcas,B soc,

J,JA ,soc 103,533 C
mlr, o

sy ,2,777-794

bight Amination KX/oight,JP

,P9, ]34,1(1886), C

Anination of bcnzoins with an ncs in the prescncc of phosphoms pcntoxme

r hydrochloHc acid:

~ռ H + ߳

0 oH

N


R

"
" C



R

c



һ

R

+H20
oNR 93

޴
388


F I



ʥ Ѻ
m
c

Volhard Erdmann

Cyc zation

:

4ɽ 1
R

mp ms

o
R o

oN

L

R

̭ 1


ss9?

I:



:t;::::fP19

s9,3210(1904) Jv n:raun,
RC0NHR

`

PCls~
29

RcN+R

I

s9

? dz : :

ڡ G
%

:
+BrCN

33 9(l99

.App ca on M butyla ide

RB.P

,

f:a

`%

ˡw : ֺ m g Ǭ
it
R2NR?

qm mm ߵ
.g.`f G Fodor,s.

һ

R2NCN+Ri:r

Mechanis c co clation with Ri cr,Bischler-Napicralski,Beckmann and schn1idt reactions,
9
fr
s Cooley,EJ.Evain,s9Pa 1989,1-7

? ; :` :Ĭ % ƹ د :ˡ ߵ ;:; ;F%
f

391

von Richter(CinnoIine)synthes

v

cs :Ʒ : ::F1 f1 :l

byɽ

m

of an noaryVm9o c ds or a inoarylacetylcncs
oH

fol

lowed by hydration and cychzation:

H-
L;

2L-?
::

-

T

R

T

ܳ

R

FH

R

J

ߡ ٲ R;e Ь f? Ramagc,,

V von Buchtcr.B r4,21,459,553(1871),

{ ² ɺ ߨ
at lzOϦ ,ɽ e oxد

392.von Richter Reaction

g :º

꡸ u|lr




t

:

s Cthahmc um w dC
ied : by the elininated nitro group:

+KCN
R

C2H5

H-

qC
R

oNR94

organiC Name Reactions

`12,15(1958);D.samuel,JC soc.82,3796(1960);E,Cullen,P rEcuyer,C .JC .39,144, 72,314(1960);M,ROsCnblum,JA,9z.C ߶ 1962,93;K,M,Ibne Rasa,E.Koubak,J 154,382,862(1961);ERU11man,EA.Bartkus,C .&J9, ro do د
˷ @rg C 28,3240(1963).
393

J,R Bunnctt,g

R

,soc1960,1318;J,saue ж

RH sgen,A g C ߶
,

Vorbrڧ ggen GIycosylation U.Nodbalk,H Xrorb ggcn,Ag
-nuclCOs es r the sugarlacks a2

C ƨE ꡣ

9,461(1970).
turc forms

Thc reac on of snylatcd hctcrocyc c bascs with pcracylated sugars in thc prcscncc of Lcwis acids to yield natural

cyloxy

substimcnt,an anomcoc m

R

ح ح
({I

lHOcl:so
LewIs acld


0
;:({}
O
st

;R

0R 0R

R C0CH3,COPh Lewis aold=BF3? 0(CH2CH3)2,snc14,(0H )osi0sO2CF3,(CH3) siCIO4,TiCI4,AICI3

`Ϧ `,B 1256 synthetic app cations:IJ Niedba a,H Xrorb ggen,J D

scopc and hmitatons

H

Vorb ggen

r114,1234(1981),Mecha

study:H VoFbmggcn,GH0

c,

(1974);R.0,Dempcy.EB.s bo, jd5 776(1991);s H Kaw ,G,Just,NJJcJ osڥds
(1991)C Hilbe ~Johnson Reaction
394

o Ch , 39,3654,3660,3664,3668,3672

of d s10,1485 c

J

WaCker OxidaJon ǡ sm t @J,A g C |E 1,176(1959l.
Thc Ox atlon of ethylene to acctaldchydc employing palladium chloHde and cupoc chlohde as catalys and mo cular oxygcn as oxidant.The reaction has becn extensively developed for thc Oxidation of terminal alkcncs to mcthyl
kctoncs

HϦ =C߳

0 cuc ,02 H3CدkH;

O R'
cuc ,%- Rد kCHa

l, L rrFrs33,7739(1992)Use of a d Appl aton to hydrox unsaturatcd estcr s X Auc1a Ϧ , 'm mult omponcnt catalyt sy em:E.Monn rrԻ l,Э j 3 387(1995),synɽ ct appI at ns:M ROmcro J,,
jDj

s9 .4,552-559(1991);J.Ts i, jd6,449-468
395

1o, 35,3255(1994);L,A,Paquette,X.Wang,J0 C 59,2052(1994).R L s Hegedus,C

` org

Wagner Jauregg Reaction t`Wagncr-Jauregg,B r63,3213(1930);^ r9,491,1(1931).

Addition of rnaleic anhydodc to diarylethylenes with fomation ofɳ jl9adducts which can bc conve ed to aromatic hng systcms:

P o ̾
~

C

C00H
H0Ac,Hl ~

oNR 95

g

¼ Fzҫ D Alder Rcaction,
ls

J

11

;lI:

( ڥ 8: ڥ u : % %
:


;ح :il !

ڥ :: Ӫ Ӯ ح
):

s:š

{Ӫ li;%

yˢ m͢ rѾ n inڥ


:3 l; z
397

:3

CH3 CH3 CH3

1;

l

ߦ ο
ֻ
: R;

:
Y _ c һ
/

`

? 3,705-7 Ѽ

WaIden Iversion R Walden,B r28,1287,2766(1895)
Inversion of con guration of a chiral center in bimolccular nuc1eophilic substitudon(sN2)rCactions: C + c~x___ -x__ / |

Y

\

x

cl_

H ^H
CH2CooH

-Pc

KoH ~

C00H H-C-0H CHϦ o0H
l
l

,Ac C H,A Bcnt,C ,R 68,587(1968);D RG.Harmon,JC ,E 47,398(1970);LK,gcr rԻ Ϧ sI1973,542;K-C.To J,,JC P ys. Ncmo n,FVr j rr 74,1499(1981).
scԻ 26,2339,2349(1972);C. 1shoppee,J
398

Waach Rearrangement
o.Wallach,L.Belh,B

`13,525(1880) Acid-cata1yzcd rearrangemcnt of azoxybenzenes to` hydroxyazobcnzcnes
N=ح ^<(IF
0


l

8;l: / f F 鴧ló ֩ Fh d,o9,36,3177(1980)
:iد

39

Ŭ G91 :: :1 aH fman ,pe react0 g%ofɽ ec T ff: Jܳ F& خ W ʵԿ
.3


-

H OH H H
H2NC0-{ oNR %

HH η 8ð Hc

H
cH20H

0_ 0HH OH0H

-{-cH2 H -

0^0 { H 0H0H

organic Na1ne Reactions
c ګ1N.Hawo h rԻ l,JC ,soc 1934,1722;1938,1975;E,s.Wa1lis,J.E Lanc,Org.R Ϧ 3,275(1946);J.C. Ϧ s,W1 gman,Ed(New York,1957)p120;L,E Fiese M ese AJv@ C Jo fc c sowden m z rDh,

C js`ʬ

`(NeW York,1961)p945.
n.3.3 pro~ d thc respective

400

Weiss Reaction

U Weiss,J M Edwards,%r L r rs1968,4885. Reaction of1,2-dicarbonyl compounds with3-oxoglutarates to yield cJs-bicyclo 330]octane-3,7-dione or
boxylates subsequent acid-catalyzed hydrolysis and dccarboxylation yie pc11ancdionc(n>2) tCta

2,4,6,8-unsubsλ tuted diones:

ʮ
E

+o+o

ll
? ߭

} ;i

i

ȥ t: % ÷
:;Ѱ 1



ķq1 /yԨ
:
temate substrates

3

ʡ



uhr

ugh Ѵ
0H H0 H0

chromones, oflavones,mav

n ls,xanthones,furan hrom

nes

R vjF,osr Wheeler,R

Forrsc

`C

co C .Pmgr18,133(1957); R,sCshadH,%r d6,169(1959);H.D.Locks1cy, rs Org,N ߶ 30,292(1973). ߶



a substiment at c



ĺ


:













methyl m

h comp m



Ac

Ac

; ҫ Ⱥ ߦ
&r rs1972,287 P Kocovsky
403

J.,CoJ`Cz c ,C ,Com ,234(1979)



Wharton ReacJon

Ps Whanon,D.H Boh1en, 0rg C .26,3615(1961);Rs,Wharton,JD 4781 Rcduction of cpoxy ketones by hydrazine to ally c alcohol ,

إ

һ ȥ




oNR 97

ػ ; κ ߦη Ҷ I׾
,

? 0 $

e ɽ ָ ӡ롰 h ether a a n$
R__ ׹L_~ Rá Cá C
RcH =cH-CH=CHR

f F 9 ջ1g
405

Ʒ
:

Ac

Wichterle1Reaction

o Wichtcde r@J ,CVJJ Cz c ,C Co .13,300(1948)

,

s-2-butcne is uscd instcad of rnethyl vinyl kcM dincaJn ofthc Robinson annulation, `,in`vhich1,3-dichloro-c tone:


D
M &Jɪ

+

lcH1)c=c(::3һ

0
R

R


L

r())t()

Ŭ׺h˽ Ԩ JF
R
C=CHR
|

a

ddv 1979,348
R

406.Widma stoermer synthesis

o Widman,B r17,722(1884);R.sto0mcr,H.Finckc,B r42,3115(1909).
synth is of cinnolines by cyclLation of(liazot cd o-aminoarylcthylcnes at room temperaturc

ɡ
R

g





:;:; f





J

l lRama
?

K.LandqѪ

, o



rDt,

moniun1polysulndc r by su1fur and a pnrnary or sccon





pm g

by aque

us m

ArCo HDnCH3һ

һ

AKCHaln+i_ NH2+ArlCH n"_C00 NH®
Ի c'3,83(1946);R,Weglcr
v rM o Prer, J

˪ i : : ߱
R vj

JM.Carmack,MA.spielman,Org.R

408.W amson synthesEs

AګL

˷ WilliaInson,JC s c.4,229(1852)

synthesis of cthers by alkylݶ ion of a1koxides wim alkyl hdides or alkyl sulfatcs:
Ro Ro

Na++RiX ~~~ RORi+NaX
Na+

Na++R s04 ~R0Ri+Rts0

oNR 98

P :: IF jc g C s rV(WilCy-Intcrscience,New York,4th
409

IƷ k : 1 ed,1992)p386,² % g;t h: ٲ
Reac

&~

W tig

on;Homcr Rcacuon;H rnc Wadsworth-Emmons RcacJon
B r87,1318(1954);G

G,V ttig,U sch0nkop

Wittig,W Haag,fDj 88,1654(1955)

Alkene formation fron1carbonyl compounds and phosphonium yhdcs,proceeding prirnarily through the proposcd
betaine and/or oxaphosphetane intcrlncdiatcs The stereoselect~ity can be controlled by the choice of ylide,carbonyl

compound,and reacuon c

nditions

Ͽʮ ح
3

Whcn thc yhdc is rcplaccd with a phosphinc Oxidc carbanion,the reaction is refe ed to as thc Horner reaction:L,

HOmcr l,B r J, `91,61(1958); Whcn thc y dc is rcplaccd with `m a phosphonate carbanion, thc rcacu n is rcfcrrcd to as the orner EI mons `92,2499(1959) Wadsworth reaCJon: s Wadswo h, , .C soc 83,1733(1961), Applic on to the syn es of unsaturatcd des:T Janeck l, ͭ sI,1721(199~s)Rel,j JA Ϧ ^D.Emmons,JA ,ƽ Maercke 0rg.oc 1 270-490(1965);K P C Vollhardt,sv 1975,765 80; L s Ѷ swOHh,J ,o R Ϧ s c ' zs,9g-253(1977 I,Gosney,A.G ROwley in0Ѽ ϦP osp os gٵ 0 Ϧ sV s J.I,G.Cadogan, Ed. (Acadenic Press,New YOrk,1979)pp17 153;B E.Maryano A,B,Reitz,C R 89,863-927(1989);s.E.KeIly,

? M Ը Ŭ;â Ƭ :f1ȣ f %Ų VPm

.4:69

410. 1,2] VV:ttig Rearrangement

G. ig,L L0hmann,A 550,260(1942);G.V"tug,EyJ, r9 14,389(1958). thѪ msto yʼ ld a ohols v ֮ Rearrangcment of cthers with alkyl 7a , -shift:

R-CH2 0 R

ӭ

L)

H+R~ߵ
R

+-

R-
R?

һ

oH

}ȩ κ ح º ҫ ح ح
; 1Ƴ 9: f

rrc g Part1,R dc Mayo,Ed.OVilCy-Intcrsciencc,Ncw YOrk, R vJ sr H.E.Zimmcrman in DfoJ rR 1963)p372 377;L Brandsma,J R Arcnsin C Erh r LJm gɫ s,Pa ֢ ,Ed lInterscicncc,Ncw YOrk, `v or
`'



(1979);



`m,

r c

CJ, .%c .

h30,483(1982)( M0senh0mcr Rearrangements;stcvcns Rearrangement.

ll;

ح
;

:l:

411.[2,3 ߵ Ϧ J.Cast J.,JC soc1960,352 U.sch011kop K.FcllCnberge B r698,80(1966);Y Makisumi,s,Notzu"ttig Rearrangement moto, %ɯ d zj rrerl91966,6393 ,3]-s matro c rearrangement ofthe co ugatc basc of allyl ethers with h h re oselect~ity The stcrcOsele
Jvity is highly dependent on the the naturc of the substratc:

0

~R~ L.~


'


J,1% J9 dro

Y=alkyn ,alken ,Ph,C0R,CN bas =LDA, BuLi,NaNH2

l r :â ƴ : ˽ . Ǧ Ũ : Evans Rcarrangcmcnt;sommelet Hauser Rearrangcmcnt.
` 412

Methods development for Hng contracuons geherating cncdiynes:H Audrain

50,1469(1994).

WohI Degradation;zcmp16n Modiflcation



A Woh1B r26,730(1893);32,3666(1899);G zemp16n,B r59,1254,2402(1926)
1by the reversal ofthc cyanohyd n Mcthod for the convcrsion of an aldose into an aldose with one less carbon ato synthcsis.In the Wohl rnethod the ni lc group is e n1inated byeatment with ammoniacal s ver oxidc;inɽ c zem

p1on modi Caon sodium alkoxide is uscd in the e

n1ination of the nitolc

oNR 99

organ Name Reac ons

HC=0

HC=NOH
NH2 H~

ߴ CH20H

H}oH

"

}

H
3

CH20H


|

CN

c

2

o

CH20Ao

?ߴ CH20H

Hl3 CH20H
.

68 118(196 ;W1 1 R sf V Dculofeu,Ao C o C 4,129,138(1949);R.Bogn `,Am d Ler rs1970,3439;L Hough,A,CR har on, C o ydn7 s1A,128(197 Wcndall, rm

ո ɽ Ѫ

k are usCd a

?
g 71,349095ߴ ne? EM? n ha hvatal,Ad`Fre -RԻ c JC 4,175-201(1972) ^ :s f F ~ kص :: Ʒ NJ I
414

Wolr shner Reduction;Huang-Minlon ModѪ caf^ 6,szI7(1912);L.Wol P,I.s c.,582(1911),C N.B shner,J R ss PsC

^
ܳ

S

Anoa

394,86(191 ;Huang-Miܳ

J

յ fh 1



qi mng

wlth hy e hydratc ab h

Hua M"om

ѽ

tion diethylcne glycol is used as a solven

o



c NHal

mH9R+

415

W Ʈī ƨ Ϲ Ⱥ F뵶
Wo r Rearrangement L.w r1AP, 394,25(1912).

ǿT
;l
:

y acu nd

ght pome mc
,
R

ic c aly̪

The

arrmgeInent k

0H

RCOCHN2

N2-

RCH==C=o

RCH2C00R

RCH2C0NHRi

~ԥ o١ B Gm,C
ӡ
416

` s

sv

3,887912(1991).

ˡ F.
:
ifح

:;I;

;};

η ˡ

:1!;iii}

:k
.

n~B0ters Reac on WoIrens o B0tcrs,R.Wolffenstein,Ge pat.194,883(1906);Fn pat.380 21(1907);Brit.pat.17¬ 21(1907);1 s.pat, 92 op nds mٳ c mc"gh od d n ¡ J: d mdѪ r on om mpoun Ѫ
nitrogcn in thc presencc of a mcrcury sa1t as catalyst:

T ?
NO2
l, mack 785;E.E

Rw 1renstcin,o

C l,JA ,soG69,773(1947);M.Car~ Boters,B r46,586(1913);RH? WCsthein1er Ի

Aristof r J,,Imd E

g

Ch m. ,1281(194 ;W

߶ s0dcnfaden,W Pawe11ek, D

W J10/1,815(1971) oNR lClCl

organic Name Reactions



: ν ߦ
һ

CH==CH
A g o



߹ ;и Lg1ϲ Ʒ

~
C I O

l l C

һGl
o

c

һ

һ c

һCl
~ A c
O

һ
~ H

C l

һCl
O

~

H




Provost ReaCuon.

٬ ѿ I
sodiun

ɮ ? mɽ m

0
419

H

0ߴ ܳ 0ߴ
lC 7,45(1982)

T L Kwa,C.Boelhouwe r dro 25,5771(1969);BJ.Wakefleld,Co

`@

Wurtz ReacJon

Ƴ h \mim a Ǵ 1 ֻ J ŭ
:
:

2RX+2Na
Ʒ ; F f 1ë o ʲ `



R R +2Nax

52 9

W m,

ߴ

C

d 4 D,G





C


gf


:

dd de and

+







-




NHa+

g


ط: ߨ
:





















l

stereoregulat

)ns rϦ J., D d475-547, 422 z mmerInann

Reac ȡr1 ٹš ߵ

on

and ar

m

pol tro nlp ndsѪ thc presen d alk

oNR=101

organic Name ReaCtions
Whcn app edto17-oxostcroids,the colorcd compounds fomed can be used for the quantitauve detcrn1ination of17oXostero1ds

;:l ff?i i:: ڥ a z
Janovsky Rcaction.
423

%.,


`1

l
n
le

zincke Disul de CIeavage

T zinckc,B r44,769(1911).

aryl d

%: m 1

r; ɻ



::



Ѫ kr me o md ngѪ don ɽ b b n

ArssAr+X2- 2ArsX
ArsH+X ArsX+HX

ArsCH2C6H5+2X2

ArsX+C6H5CHX2+HX

:s . ؾ h, 1
11 rI

.391,55(1912);400,1(1913);406,103(1914);416,86 T Zincke r l,B r45,471(1912);51,751(1918);A
R

v39,283c9 ?
atomsl h phenols

::}

424

zincke Nitration 61,561(1900). T,zinckc,J PrԻ C

J %

l

1

lliح

ٲ ح
l

tn t٤ mne r chl







:

NO2

+ NaN02 CH3COoH~

+ NaBr

8 r ح ,ȵ :: ѥ ȵ ܳ
:?
:{
{;; ; I

425 zincke

suhI Reac on

V

thC pre



Ѫ mm chlo

li

ҫ
















C C


H



o H

M,s Ncwman,A.G,
C soc.8
128.

nkus,JC, C ,19,978,985,992,997(1954);Ms.Newman,L L Wood,J ,JA dR dR voI? I ntCrscʼ nCe,Ncw York,1963)p cr s 6450(1959);G? A.olah,Frj JVJ C s

,

oNR 102

organic Na ne Reac ons

INDEX
BoIdface numbcrs rcfer toɽ e
p mary

en1

4CC,382
Acetoacetic Ester Condensation,72
Acetoaceλ c Ester synɽ csis,1

Blaise-Malrc Reaction,43
Blatse Reactlon, Blanc s BouvcauIt Blanc Rcduction,54
1; 4ح

Acyloin Condensation,2

Blanc(ChloromcthylaJon)Reaction,45
Blanc Rcaction-Blanc Rule,46 Bodroux-Chichibabin Aldchyde synthesis,47

Akaboo Amino Acid Reactions,3 A1der s Dlel Alder ReacJon,97,113;Retro-Diels-Alder Reac on,318

Bodroux Rcaction,48
Bogert-Cook synɽ esis,49

A1dc Enc Rcactlon,I13

A1dol Reaction(Condcnsation),4,12,92,159,284,325 retro,92 A1gar Flynn-oyamada Rcaction,5
Allan-Robinson ReaC on,6 A y c Rcarrangcments,7

Bohn-schmidt Reaction,50
Boord O1cfln syn esis,51 Borodinc Reaction,190 Borschc-Drcchsel Cyc zation,52 B0ters s Wolffenstcin-B0ters Reaction,416 Bouvcault ldehydc synthesis,53 Bouveault-Blanc Reduction,54

Aluminum Alkoxidc Rcducdon s Meerwcin-POnndorf lrerIey Reduction,240,270 Amado Rea angement,8 Amidine and0 ho Ester synthcsls,297 Arbuzov(Arbusow)Rcactlon s Michacli Arbuzov Reacton,

249
Arens-van Dorp synɽ c s,9 Amdt Eiste synmesls,10,415 Auwers synthests,11 Babayan s Favorskii-Babayan synthesis,117 Bachrnann s Gonnberg Bachrnann Reaction,149 Back1und s Ralnberg-Backlund Reaction,310 Baeycr-DrcWson Indigo synthcsis,12
Bacycr- qlliger Rcaction,13

Boyland-sims Oxidajon,55 Bradshcr Rcacjon,56 von Braun j Rosenmund-von Braun synɽ esis,328
Von Braun Amide Degr?adation,389 von Braun Rcac on,390 Brown1ng Reacλ on,233 Brown-Walkcr Reaction s Crum Brown Walker Reaction,211 Brunner s Einhom-Bmnner Reaction,108 Bucherc Bcrgs Reacjon,58 Bucherer Carbazole synthcsis,59 Bucherer Rcaction,60 B chi s Paterno-B chi Reaction,276 Buchne Cu ius sch1ottcrbeck Reaction,61 Buchner Mcthod of Ring Enlargemcnt,62

Brook Rcarrangement,57

Bakcr-Vcnkataralnan Rcarrangcment,14 Balz-schiemann Rcaction,339

Balnbergcr Rcadangcmcnt,15
Bamford-stevens Rcaction,16 Barbler 0pel Reacλ on,17 Barbic WlclaIld Dcgradation,18,250 B Rcaction,19 Ba on Deoxygena on,20 Banon~Kcl1ogg Reaction,21 Ba onJ cCombic Rcaction,20 Banon olcfln synthcsis,21

& W Ʒ
l I FϢ

khell karrangc m,141

Banon Reaction,22
Baudisch Rcaction,23 Baucr s Halle Bauer Reaction,161 Baumann s schotten-Baumann ReaCtion,343 Baylis-H lman Reaction,24

179 :: Ϣ synm dne 1:1 Cnt,65 : Rcaction,69 h dehy mhesls Chichibabin

B6champ Reduction,25 Beckmann Fragmentation,26

Beckmann Rcadangement,26,390
Bellcau s FuJimoto-Be11cau Rcaction,102

ɪ ::} Jsf angemcnt,71 :::s
Ch:
(


d n, s

:ls:

Ciallllcian-Dennstcdt Rea͡

Fcist-B6nary synthcsis,119 Benary Reac on,27 Benkescr Rcduc on,28 Benzidinc Rcarrangement,29 Benz -Benz ic Acid Rearrangement,30 Benzilic Acid Rearrangement,30 Benzoin Condensation,31 Bergius Proccss,32
B nary s

ClaIscn s Darzens-Cl scn Reaction,88

Clalsen Condensation,72,96
Clè scn Rcarrangemcnt,73,79

ClaIscn-schmidt Condcnsation,74 Clarkc s EschweileClarke Reaction,224

Clemmcnscn ReduCuon,75,167

Bergman Reaction,33
Bergmann Azlactone Peptide synthesis,34

Collins Oxidation,338 Colman s Gab c Colman Rearangcment,143 Combes Quino ne synthesis,76

Bergmann Degradajon,35 Bergmann-ze as Carbobenzoxy Mcthod,36
Bergs s Bucherer-Bergs Reaction,58

Conia Reacuon,I13 Conrad-Limpach Reaction,77 Contardi s 0me Contardi ReactIOn,337
Cook s Boge -Cook synthcsis,49

Bem1thsen Acndine synɽ esis,37
Betti Reaction,38

Cope Eliminatlon Reaction,78
rctro-,78

Beyer Memod for Qulnolines,1 ltl
Biginelli Rcaction,39

Copc Rea angemcnt,79

Corcy-Kim Oxidation,80
Corey nter olefln syn esls,81 Cornforth Rearrangcmcnt,82

Birch ReducJon,40
Bischler-M0hlau Indole synthesis,41 BischIe Napieralski Reaction,42,390
BiɯLac m

Coumaon-Benzofuran Ring Contraction,285
Crafts s

Amino Acld synthes^s schdlkopf Bis-Lactim

F edc Crafts Reaction,138,167,261
4I

AFnino Acid synthesis,342 Blaisc Kctone synɽcsis,43

Craig Method,ss
CHcgee Reaction,1:;

oNR 03

organk Name ReacJons
Cmm Brown-Walker RcaC on,211 cumus Reaction,85
Cu ius Rearrangement,85 Dakin Reaction, Dakln-West Reaction,87 Darzcns-Claiscn Reaction,Bg
Fische spoer EsteofIcation Mcthod,129 Curtius BuChne Cu ius-schlotterbeck Reac on,61

Darzcns Condensaton,88
Darzcns-Nenitzescu synmcsis of Ketones,89 Darzcns synthesls of Tera n Denvatives,90 De16pine Reaction,91

Fischer-Tropsch synthcses,130,272 Flttig s Vunz-Fittig Reao on,418 F1ood Rcaction,131 Flynn s A1gar- ynn-oyamada Reaction,5 Forstcr Reaction,132,133 Fou Component Condensation,382 Franchimont Reaction,134 Franklaild-Duppa Reaction,135 Frank1and syn esis,136 Frcund Rcaction,137 Frcytag s Hofnlann-L0 e Freytag Reaction,182



Dess-Ma"in Oxidation,94
Diec mann

ˡ
,95

6

Fncdcl-Craft$Reaction,138,167,261
Fncdlacnder synthesis,139

D-Homo Rcarrangement of sterok

Reaction,96

=

Focs Rcarrangcmcnt,140 F tsch s POmcranz-Bˮtsch ReaCtion,301
Fntsch-Buttcnberg-Wlechell Rearrangement,141 R imot BCllcall Rcactlon,142

?

Diels-Alder Reaction,97,113
rero 318 Diene synthesis s Diels-Alder Rcaction,97,113

Gaboel-Colman Rearrangcmcnt,143 Gaboel Ethyleniminc Mcthod,1

GabneH qllino1ine.synt sis,1
Gab e Marckwald Ethylcnimunc synthesis,144 Gab el synɽ csls,145 Gamss te Gams Isoquino1ine synɽ esls,292 P Gattenann A1dchyde synthesis,146

Dienonc-Phcnol Rcarrangement,98
(Dihydro)Py dine synthesis,163
f:
s

G Ӿs

E az

k don,153

DoebneMillcr Reacuon,1oo
Doebner Modiflcation of Knoevenagcl Condensation,203

Gattcrmann-Koch Rcaction,147 Gattcmann Rcaction,337
Glaser Coupling,148 Glycidic Ester Condensation,88 Goldbcrg se Jourdan-U11mann-Goldberg synthesis,198 Golnbcrg-Bachnnann Reaction,149 Gomberg Frcc Radlcal Reac on,150 Gou1d-Jacobs Rcaction,151 Gracbc-Ullmann synthcsis,152 Gocss DiazO Reactlon,153 qgnard Degrad ion,Is4

Doebner Reacdon,101

բ D0tz Reaction,103
:
Ii

;

Duf Rcaction,104

:;:%, Т ح
kac
:I IIlJ: :s

B:
Einhom s

ߴ135

ح ,lO9 }ic Tschemiac-Einhom Reaction,380
:1iح
{!ح :

Gognard Reacjon,155 Gognard Reagen127,47,48,51,53,142,154,155,179
Grob Fragmentation,156
Gro9heintz-Fische Reisse AIdehyde synthe s,316

Einhom-Bmnner Rcaction,108

Gmndmann Aldehyde synthesis,157
Guareschi Thorpe Condensation,158 Guerbet Reactlon,159 Gustavson Reaction,137 Gutknecht Pyrazinc synɽ esis,160 Haack s Vllsmeie Haack Reacjon,386 HaafiKoch-Haaf Carboxylations,208 Halle Bauer Reaction,161
Halofo n ReacJon,226

nimsf ָ m . Ӫ F; l
n

227

Elbs Persulfate Oxida on,109

Elbs Reaction,110

Emde Degradatlon,111
Emmc Reaction,112
Ene Reaction,113 : Eschenmoser Fragmenta on,11s Eschenmose Tanabe Fragmcntatlon,II5 خ



Emmonss HOme Wadswo h-Emmons Reaction,409
mh sis 11z1

Halnmick Reacjon,162 Hantzsch(Dɽ ydrolPyodlnc synthes`,163
Hantzsch Pyrrclle synthcsis,164

Hames Ozonidc RcaCtion(ozonolysis),165
Hass Cyc1opropane Process,137 Hauser s so 1melct-Hauser Rearrangement,354,359

EschweilerCIarke Reacuon,224

Hawonh Mcthylation,166

tard Reaction,II6 Evans s Mislow-EVans Rearrangement,253

Hawo

Phenanthrene sy s,167

t," W%ա ή
Favorskii Rearrangement,118
j

Hayashi Rcarrangcment,168 Heck Reaction,169,368 Hclfeoch Mcthod,170
Hcl Volhard Zclinsky ReaCtion,17I

::: Fenton ReactIOn,120
: ::

radaj

.3s1

Henkel Process,172 Henkel Reaction,172

Hen9Reacλ on,173
Hepp s sche Hepp

Fenoer Rearrangement,121
Finkelstein Reaction,122

Rearangemcnt,123

; 궦 f˪ 316
:l

Herz Compounds,174

: : ;{i:s:



l;;

߱

::18r%l :

n3


oNR 104



Herz Reaction,174 Hilbe -Johnson Reaction,175 Hillman s Baylis-Hi11man Reaction,24 Hinsberg oxindde synthesis,176 Hinsberg sulfone synthcsis,177 Hinsberg synthcsis of t iophene Denvatives,178 H h-Campbell Az"dine synthe s,179

H sch

se Houben-Hoesch ReactIOn,188 Hofmann Degrada on,111,180

organic Name Reactions
Hofmann Isonit le synthesis,181 Hofmann-L0mer Freytag Reaction,182 Lieben Iodoform Reaction,226 Limpach J Conrad-Limpach Rcaction,77 Lob de Bruyn-van Ekenstein Transfomation,227 Lomers Hofmann-L0 e Freytag Reaction,182

HOfmann-Ma ius

Rea angement,183

Hofmann Rcaction,184,399 Hofmann-sand Reat"ons,185 Hooker Reaction,186

Homcr Rcacjon,409 Home Wadswo h-Emmons Reaction,0l 9
Hosomi-sakurai Reaction,334 HOubcn-Fischer synthesis,187

LOssen Rearrangcmcnt,228 McComblc s BaHOn-McComble Reaction,20 McFadyen-stevens ReaCtion,229 McLaffe y Rearrangement,230

McMu y

Reaction,231

Madelung synthcsis,232
lard Reaction,233 Ia aire s BlaIsc-Malrc Reactlon,43 Malaprade Reaction,234 Malonic Ester synɽ cscs,235

Houben-Hoesch Reaction,188 Houdq Cracking Process,189
Huahg-Minlon Modiflcation of Wolr Kishner Reductlon,414 Hube s Picte Hubc Reaction,293 Hunsdiecker Reaction,I90 Hydroboration R action,191

Mannich Reaction,236 Marckwald s Gaboc Marckwald Ethylenimine synthesis,100
Marschalk Reaction,237 Manin s Dess-Manin0 daton,94

Hydrofomylatlon Reaction,272
IndireCt Diazotlzation Method i9

Gness Diazo Reaction,153

Iodofonm Reaction s Lieben Iodofom Reaction,226

Irc1and-Clatscn Rearrangement,73 Irvine-Purdie Methylajon,308
Islcr Modiflcation ofArens-van D rp synthesis,9

Ivanov Reaction,192 Jacobs s Gould-Jacobs ReacJon,151 Jacobsen Epoxidatlon,193

Ma inet Dioxindo1e synthesis,238 Martius s Hofmann-Madius Rearrangcmcnt,183 Mattox s Kendall-Mattox ReacJon,200 de Mayo Reaction,92 Mcep ein Arylation,239 Mecp cin-POnndorf Vedcy Rcducuon,24o,270 Mee in Rearrangemem s Wagner MeerWeIn Rcarrangemem, =
Meiscnheimer Rea angements,241

Jacobsen Rearrangement,194 Janovsky Reaction,195 Japp-Klingemann Rcaction,196 Jauregg s Wagnc Jauregg Reaction,39s
Johnson s Hi1be -Johnson Reacλ

Mcnschutkin Reaction,242
MeHifleld so d-Phase Peptidc synthesis,243

on,175

Johnson-Cl scn Realrangement,73
Joncs Oxida
Ju a

Meyer Reaction,244 Meycr-schuster Rearrangement,245
Meyer synthesis,246 Meyers A1dchyde synthesis,z09

Jou -Ullmann-Goldberg
olcflnation,199

on,197

synthesis,198

Michael Reaction(Addition,Condensation),4,217,248 Reacuon,21
Michac s-Arbuzov Reaction,249 Mieschcr Degradation,250

Ke11ogg s Barton-Kellogg

Kendal Mattox Reaction,2 Khand s Pauson-Khand Reaction,277 Ki ani-Fischcr synthesis,201 Kim s Corcy-Kim OxidaJon,80

Mignonac Reaction,251 Mnas Hydr xylat on of ole ns,2s2
Millcr s

D bne Mi cr Rcaction,100

Kindler Wlllgerodt-Kindler synthesis,409 Kishner s Wolff X shner Reduction,167,414 Kishner Cyclopropane synɽ esis,202 Klingemnann s Japp-Klingemnann Reaction,196

Mislow-Evans Rearrangemcnt,2s3 Mitsunobu Reaction,254
Moffatt Oxidation,291

Moffatt-swcm Oxidation,370
M0hlau s Bischle M0hlau Indo1c synthesis,41

Knoevenage1Condensauon,2o3
Knoevenagel Diazouzation Meɽ od,153 Knoop-Ocstcrlin Amino Acid synthesis,204 Kn0͡ s Koenig Knorr synthe s,21 Paal-Kno Pyrrole synɽ csis,273 Kno Pyrazolc synthesis,205
Knorr Pyrr ,1e synthesis,206

Walls ReacJon,293
`-orga Moser s Wessely-Moser Rcarrangement,401 M ller React on,301 Method,356 Nagata Hydrocyanation,2s5 Nametkin Rcarrangement,256
s POmeranz-Fotsch

M111er s sonn~Mu er

Kn0͡ Quinolinc synthesis,209 Koch s Gattennann-Koch Reacjon,147
KOch-Haaf CarboxylatIOns,208 KOchi Rcaction,209 Koenigs-Kno syn esis,210
Kolbc Electro1ytic synthesis,211

Napieralski s BischlerNapieralski Reaction,42,390

i

Zieglc Natta Polyme"zation,421 Nazarov Cyc zation Reacjon,257
Natta s

Ncbcr Rearrangement,258
Nef Reacλ on,259,260 Nef synthesis,260 Nencki Reaction,261 Ncnitzescu s Darzcns-Ncnitzescu synthesis of Ketoncs,89 Nenitzescu Indolc synɽesis,262 Neni escu Reductive Acy1ation,263
Nicholas Reac

Kolbc-schmitt Reacλ on,212 K0mc ContardI Reaction,337 Kostanecki Acylation,213 Kiafft Degradation,214

Krapcho DccarbalkoXylajon,215
Krltschenko s Petrenko- tschenko Pipeodone synthesis,288

on,264

Kr0hnke Oxidation,216
Krohnkc Pyidine synulesis,217

N mentowski Quinazolhe synthes ,265 N mentowski Q noline synthesls,266
Nierenstcin Reaction,267

Kucherov Rcaction,218
Kuhn-Wlnterstein Reaction,219

Noaosh Typc Cleavage,268 Noyon Hydr genation,269
s Knoop-Oesterlln Amino Acid synthe s,204 oppenauer Oxida on,240,270

Ladenburg RcaJangement,220
Lcbedev Process,221 Lehmstedt Tanasescu Reaction,222 Lett s Westphalen-Lett6Rearrangement,4o2
Letts Nit le synthesis,223

oeste in


oxo synthesis,130

nlent,

Leuckan Reacjon,224
Leuckan-Wa11ach Reaction,224 Leuckad Thiophenol ReacJon,225
Leukam s Leucka

oxy-Cope Rearrangcmcnt,79 oyamada s Alga Flynn-oyalnada Re tion,5
Paa Knorr Pyrrolc synthcsis,273

Parham Cyclization,274

oNR 105

organic Name Reactions
Passeoni Rcaction,275

Patemo-BJchi Reaction,276 Pauson-Khand Reaction,277

sabatic scndcrens Reduction,333 sachs s Ehdich-sachs Reaction,107

Ʒ 9,351 s,280 Pcchmann Pyrazole syn
C

sakurai Reaction,334 sand s Hofmann-sand Rcactions,185 sandmeyer Diphenylurca Isatin synthesis,335 sandmeyer Isoni osoacetanilide Isatin synthesis,336

Pellizza Reaction,281

sandmeyer Rcaction,337
sarett Oxidation,338
scheller Modiflcation of Ba Reaction,19

Pclouze synthesis,282 Pc od Acld Oxidation,234 Pcrkin AIicyc c synthcsis,283 Perkin Reaction,284 Perkin Rearrangement,285

Perkow Rcaction,286
Peterson Reaction(Oleflnation),287 Petrcnko-Kritschenko Pipeodonc synthcsis,288
Pfau-Plattner Azulcnc synthesis,289
: : l

schiemann Rcaction,339 sch ttle Muller ModifICation of Pomeranz-Fotsch ReaCtIOn, 301 BuChne Cu ius-schlo erbeCk Reac on,61 schlotterbeck s schmidt se Bohn-schmidt Reaction,sO;CIaisen-schmidt Condensatlon,74

schmidt Reaction,340,390
schmitt s Kolbe-schmitt Reaction,212

i: n,29I

scho Rcacti0n,341 sch0 kopf Bis-Lactlm Amino Acid synthesis,342

:I 碷ԢF Ʒ inѪ Rearrangemcm Plctct-Gams IsoquInolinc synthesls,292
Pictct-Hube Reaction,293

Robinson-schopf sch0pf s

ǿ

Pinner Rcaction,297


4

Rcacion,326 schotten-Baumann Rcaction,343 Mcyer-schustcr ReaHangement,245 schuster s
selenium Dioxidc Oxidation,323

semidine Rearrangemcnt,29 scmmlc Wolf Rcaction,344
senderens s sabatler-senderens Reduction,333

Pinner Triazine synthesis,298
Pi a Rcaction,299 Plattner s Pfau-Plattncr

Azulene synthesis,289

Plochl s Edcnmeye P16chl Azlactone and Amino Acid synthc-

sis,114 Polonovski Rcaction,300 Pomeranz-Fitsch Reaction,301 Ponndorf s ٢ eenl,cin-Ponndorf Vcrley Reduction,240,270 POnzio Reaction,302 POtle Polonovskl Reaction,300 P߸vost Reaction,303 P"lezhaev(PrileschaJew)Rea ion,sO4 P ns Reaction,305 PsCho ReaCtion, 49,306

se"ni Reaction,345 shapiro Reaction,16 sharpless Dihydroxylation,346 sharpless EpoXidation,347 sharpless Oxyamination,348 sirnmons-smmh Rcacti n,349 simonini Reaction,350 simonis Chromonc Cyclization,351 sims s Boyland sims Oxidation,55 skraup Rcaction,352

Pummerer Rea angcmcnt,307
Purdie Methylation,308 Quelet Reaction,309 Raecke Process,172
l :l ::: I

smiles Rcarrangcmcnt,353 smith s simmons-smith ReaCtion,349 sommclct-Hauser Rcarrangcmcnt,354,359 sommclct Rcacdon,355 sonn-Mu11cr Mcthod,356 Fische speier Esterlic ion Method,129 spcicr s
spcngler s Picte spengler Isoquino ne synthesi$,294

staudinger Rcacjo ,357

13 Ѵ
d

310

stephen Aldehyde synthesis,358 stephens-Castro Coup1ing,66 stcvcns s Balnford-stevens Rcacjon, 16;McFadyen-s vens

Rcacjon,229
stevens Reaangement,354,359 stieg tz Rearrangement,360
st le

Reissc Indole synmesis,315

Coup ng,361

η ر :
l;

Rcro-Aldol Rcaction,92

: ::i ,31: smem,319 nthesis,391 ;:lη ح : uɪ ־ 322 Ĭ g ym If19 :˼ binson Reacλ on,6;Pilo -Robinson synb :::l


stobbe Condensation,362 stoenner s dman-stocmcr syn esis,406 stoll6synthesis,363 stork Enamine Reaction,364 strecker An no Acid synɽ csis,365 s ecker Degradation,366
strecker sulfIte Alkylatlon,367
suhl s

e zinckc-suhl Rcaction,425

suzukl Coupling,368 swa s Reaction,369 swcrn Oxidation,370
synɽ ol Proccss,130 Tafcl Rcarrangcmcnt,371 Tanabc l Eschcnmoser-Tanabe Fragmentation,115 Tallascscu s Lchmstedt-Tanasescu Reaction,222 Tcbbc Oleflnatlon(Methylenatlon),372

R

1 llan~R

::

Tebbe Reagent,372
Thiclc Reao on,373 Thiclc- 1nter AtetoXyla on,373 Thorpe s Guareschi-Tborpe Condensation,158

η l: lgcsis,328 :::l :
:

j1I;

,

Thorpe Reacjon,374
Tholpe-Ziegler Me od,420 Tlcmann s Reime q emann Reaction,314

Ruff Fenton Degradation,331


9

;(l;ܼ

332 1 e

Tlemann Rearrangemcnt,375

oNR lOf

orga c Name Reac ons
TlffeneauOen anov RCarrangement,376 Tishchenko Reaction,377 Traube Pu ne synɽ esis,378 Tropsch s Fischer-Tropsch syntheses,130,272
Trost Allylation,379

`llach Rcarrangement,398 Walls s Morgan-Walls Reacλ on,293

Weeman Dcgradation,399

Tmce-sn1iles Rearrangemcnt,353 Tschenuac-Einhom React on,380 Tschitschibabin s Chichibabin Tschugaeff s Chugaev TsuJi-Trost Rcaction,379 Twitche Process,381 Ugi Reaction,382 Ullrnann Graebe-Ullmann synthesis,152 Ullrnann Jourdan-U11 nann-Goldberg synthesis,198 Ullmann Reacλ on,3

Weiss ReaCtion,400 Wessely-Moser Rcarrangement,4 1 West s Dakin-Wcst Rcaction,87 Westphalen-Le Rcarangcmcnt,402 Whaon Reaction,403

WhiJng Reacuon,4o4

Ultee Cyanohydon Method,384 Urech Cyanohydnn cthod,384
Urech Hydantoin synthesis,385 van Dorp Arens~van Do p synthesis,9 van Ekenstcin s Lobry de Bruyn-van Ekenstcin Transfomation

W1chterle Rcaction,405 dman-stoenmer syn esis,406 V echell s Fotsch-Buttenberg- V1echell Re angcment,141 W1eland s Barbie 1eland Degradaion,18,250 ` W1 gerodt-Kjndlcr Reaction,407 Wll amson synthcsis,408 1nter s Corey-Winter OlefIn synthcsls,81;T"ele-Wlnter Acetoxy1ation,373 Winterstein t9 Kuhn- nterstein Reaction,219 Wltt Diazotization Method,153
Wlttig Reac

on,372,409

227
Venkataraman se Bake Venkataramnan Rearrangemcnt,14 Vedey s Meenein-Ponndorf Verley Reducdon,240,270 Victor Meyer synɽ esis,246 1lliger s Baeyer-1lligcr Rcaction,13 Vi1smeie Haack Reaction,386

Wohl Degradation,412

,2 Wlttlg Rcarangement,410 ,3 Wlttlg Rearrangement,411

Wohl-Zieglcr Reaction,413
Wol f Aron1atizatlon,344

Wolff X shner Rcduction,167,414

Voight Amination,387 Volhard s Hell-Volhard-Zc nsky Rcaction,171 Volhard-Erdmann Cycllzation,388 von Braunl Rosenmund-von Braun synthesis,328

wolr Rearrangcrnent,415 wolr scmm1cr Aromatization,344

WoodWa i

Wolffenstcin-B0tcrs RcaCλ on,416 cjs-Hydroxylation,417

Von Braun Amide Dcgradation,389
von Braun Reactlon,390 Von Richtcr(Cinnoline)synɽ esis,391 von Richter Reacjon,392 Vorb ggen Glycosylajon,393

Wonnalli Dutt-Wonnall Reaction,105

Wu z-FittIg Rcaction,418 Wu z Reaction,419
zelinsky s Hel Volhard Zelinsk,Rea lon,171

Wacker Oxidation,394

Wadswo hs Home Wadswonh Emmons Reaction,409
Wagner-Jauregg Reaction,395

Wagner-Meerwein Reanangement,396
Waldcn Invcrsion,397 Walkcr s Cmnn BrOwn Walker Reaction,211 Wa11ach s' LeuCkan-Wallach Reacλ on,224

zernp16n Modi cation of Wohl Degradation,412 zervas Bergmann-ZcrVas Carbobenzoxy Mcthod,36 ziegler s Woh Ziegler ReacJon,413 Ziegler Mcɽ od,420 ZieglerNa a Polymeozation,421

Zimmemann Rcaction,422
Zincke Disul dc Cleavage,423

Wa1lach Dcgradauon,118

Zincke Nltrauon,424 Zincke-suhl Rcaction.425

oNR 09


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