Organic Reactions, Volume 2

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COPYRIGHT, 1944 BY ROGER ADAMS AU Rights Reserved This book or any part thereof must not be reproduced in any form without the wntten permission of the publisher. Third Printing, December, 1946 PRINTED IN THE UNITED STATES OP AMERICA
PREFACE TO THE SERIES In the course of nearly every program ofresearch in organic chemistry the investigator finds it necessary to use several of the better-known synthetio reactions. To discover the optimum conditions for the application of even the most familiar one to a compound not previously subjected to the reaction often requires an extensive search of the literature; even then a series of experiments may be necessary. When the results of the investigation are published, the synthesis, which may have required months of work, is usually described without comment. The background of knowledge and experience gained in the literature search and experimentation is thus lost to those who subsequently have occasion to apply the general method. The student of preparative organic chemistry faces similar difficulties. The textbooks and laboratory manuals furnish numerous examples of the application of various syntheses, but only rarely do they convey an accurate conception of the scope and usefulness of the processes. For many years American organic chemists have discussed these problems. The plan of compiling critical discussions of the more important reactions thus was evolved. The volumes of Organic Reactions are collections of about twelve chapters, each devoted to a single reaction, or a definite phase of a reaction, of wide applicability. The authors have had experience with the processes surveyed. The subjects are presented from the preparative viewpoint, and particular attention is given to limitations, interfering influences, effects of structure, and the selection of experimental techniques. Each chapter includes several detailed procedures illustrating the significant modifications of the method. Most of these procedures have been found satisfactory by the author or one of the editors, but unlike those in Organic Syntheses they have not been subjected to careful testing in two or more laboratories. When all known examples of the reaction are not mentioned in the text, tables are given to list compounds which have been prepared by or subjected to the reaction. Every effort has been made to include in the tables all such compounds and references; however, because of the very nature of the reactions discussed and their frequent use as one of the several steps of syntheses in which not all of the intermediates have been isolated, some instances may well have been missed. Nevertheless, the
Page 1: Organic Reactions VOLUME II EDITORI
Page 5 and 6: CONTENTS CHAPTER ' PAGE 1. THE CLAI
Page 7 and 8: 2 THE CLAISEN REARRANGEMENT PAGE Ta
Page 9 and 10: THE CLAISEN REARRANGEMENT STRUCTURA
Page 11 and 12: THE CLAISEN REARRANGEMENT ,—C(CN)
Page 13 and 14: 8 THE CLAI8EN REARRANGEMENT A diffe
Page 15 and 16: 10 THE CLAISEN REARRANGEMENT OH %CH
Page 17 and 18: 12 THE CLAISEN KEARRANGEMENT rearra
Page 19 and 20: 14 THE CLAISEN^EEAREANGEMENT Simila
Page 21 and 22: 16 ' THE CLAISEN REARRANGEMENT by r
Page 23 and 24: 18 THE CLAISEN REARRANGEMENT provid
Page 25 and 26: 20 THE CLAISEN REARRANGEMENT curie
Page 27 and 28: 22 THE CLAISEN REARRANGEMENT r meth
Page 29 and 30: 24 THE CLAISEN REARRANGEMENT Ethers
Page 31 and 32: 26 THE CLAISEN REARRANGEMENT allyl
Page 33 and 34: 28 THE CLAISEN REARRANGEMENT pressu
Page 35 and 36: None Ring Substituents in OHo-sCHOH
Page 37 and 38: Ring Substituents in 2-Hydroxy * 3-
Page 39 and 40: 4-Carbethoxy Ring Substituents in 2
Page 41 and 42: Compound 2-AHyloxybiphenyl 2-Allylo
Page 43 and 44: Ring Substituents in CH2=CHCH2OC«H
Page 45 and 46: CH-CHCHO^N Allyl Group /3-Chloro /3
Page 47 and 48: Compound 2-Cinnamyloxy-3-carbometho
Page 49 and 50: 2,6-Dichloro 2,6-Dibromo Compound R
Page 51 and 52: Compound 7,7-DimethylaUyloxyfuranoc
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48 THE CLAISEN REARRANGEMENT 104 Ki
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50 ALIPHATIC FLUORINE COMPOUNDS ^~
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52 ALIPHATIC FLUORINE COMPOUNDS ace
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64 ALIPHATIC FLUORINE COMPOUNDS of
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56 ALIPHATIC FLUORINE COMPOUNDS Fro
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58 ALIPHATIC FLUORINE COMPOUNDS pro
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60 ALIPHATIC FLUORINE COMPOUNDS Rea
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62 ALIPHATIC FLUORINE COMPOUNDS rem
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64 - ALIPHATIC FLUORINE COMPOUNDS m
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66 ALIPHATIC FLUORINE COMPOUNDS com
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68 ALIPHATIC FLUORINE COMPOUNDS to
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70 t ALIPHATIC FLUORINE COMPOUNDS t
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72 ALIPHATIC FLUORINE COMPOUNDS flu
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74 ALIPHATIC FLUORINE COMPOUNDS men
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(CF)* CFBr3 CFCI3 CFN CF2Br2 CF2C12
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Formula C2F2Br2O C2F2Br4 C2F2CI1! C
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Formula C2HF2Br C2HF2B1O2 • C2HF2
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Formula C2H2F2O2 C2H2F3Br C2H2FSC1
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Formula CW3U C3F3CU C3F4Br2Cl2 CgF4
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Formula CaHsFO CsH6FO2 C3H5F2Br C3H
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Formula C4HrFOj C4H7FjBr0 C^FsNjOi!
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Formula CeHiaF , C6H13FO2 C7H8F3O4
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92 .' ALIPHATIC FLUORINE COMPOUNDS
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CHAPTER 3 THE CANNIZZARO REACTION T
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96 THE CANNIZZARO REACTION these en
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98 THE CANNIZZARO REACTION hyde. It
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iOo THE CANNIZZARO REACTION R CH3 C
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102 THE CANNIZZARO REACTION of the
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104 THE CANNIZZARO REACTION reactio
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106 THE CANNIZZARO REACTION least o
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108 THE CANNIZZARO REACTION Hydrohy
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110 THE CANNIZZARO REACTION however
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112 THE CANNIZZARO REACTION m-hydro
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CHAPTER 4 THE FORMATION OF CYCLIC K
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116 THE FORMATION OF CYCLIC KETONES
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118 THE FORMATION OP CYCLIC KETONES
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LXXII TTgYTTT 40 Bachm'ann and Stru
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152 THE-FORMATION OF CYCLIC KETONES
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CHAPTER 5 REDUCTION WITH ALUMINUM A
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180 REDUCTION WITH ALUMINUM ALKOXID
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CHAPTER 6 THE PREPARATION OF UNSYMM
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226 THE PREPARATION OF UNSYMMETRICA
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232 THE PREPARATION OF UNSYMMETR1CA
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240 THE PREPARATION "OF UNSYMMETRIC
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244 ' THE PREPABATION OF UNSYMMETRI
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246 THE PREPARATION OF TINSYM METRI
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248 THE PREPARATION OF UN8YMMETRICA
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254' THE PREPARATION OF UNSYMMETRIC
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2&8 THE PREPARATION OF UNSYMMETRICA
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258 THE PREPARATION OF UNSYM METRIC
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CHAPTER 7 REPLACEMENT OF THE AROMAT
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264 THE AROMATIC PRIMARY AMINO GROU
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294 THE AROMATIC PEIMARY AMINO GROU
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Aniline Benzidine «-Naphthylamine
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TABLE II—Continued ETHANOL DEAMIN
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p-Aminobenzoic acid Amine 3-Methyl-
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O2N- NOs OCHjCOOH NH8 COOH NH, TABL
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NH, >\ TABLE II—Continued ETHANOI
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Amine 2,3,5-Trichloro-4-hyaniline 2
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Amine 2-Nitro-3'-bromo-4'-aminobiph
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Amine 4-Ammo-5-methylbenzene-l ,3-d
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HOsS TABLE II—Continued ETHANOL D
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SO,H TABLE II—Continued ETHANOL D
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TABLE II—Continued ETHANOL DEAMIN
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Aniline Benzidine jS-Naphthylamine
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NH, TABLE III—Continued HTPOPHOSP
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OCH, v • NO* Amine 3-Nitro-4'-ami
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CH, Br—it^V-Br ILJ-NH, Br—IIJ
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NH; i CH8 TABLE III—Continued HTP
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Aniiinft o-Toluidine p-Toluidine 2,
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Aniline a-Naphthylamine 2,3-Dimethy
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CH3 Amine (ca. 35%) TABLE V—Conti
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H,N TABLE VI—Continued DEAMINAMON
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342 PERIODIC ACID OXIDATION If the
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344 PERIODIC ACID OXIDATION the pro
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346 PERIODIC ACID OXIDATION elevate
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348 PERIODIC ACID OXIDATION If the
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350 PERIODIC ACID OXIDATION Since e
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352 PERIODIC ACID OXIDATION dihydro
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354 PERIODIC ACID OXIDATION H 0=C
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356 PERIODIC ACID OXIDATIOM LI or L
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358 PERIODIC ACID OXIDATION Crystal
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360 PERIODIC ACID OXIDATION pended
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362 PERIODIC ACID OXIDATION A solut
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364 PERIODIC ACID OXIDATION The eth
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366 PERIODIC ACID OXIDATION PRODUCT
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CHAPTER 9 THE RESOLUTION OF ALCOHOL
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378 THE RESOLUTION OF ALCOHOLS indi
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380 THE RESOLUTION OF ALCOHOLS volv
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382 THE RESOLUTION OF ALCOHOLS acti
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384 THE RESOLUTION OF ALCOHOLS and
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386 THE RESOLUTION OF ALCOHOLS and
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388 THE RESOLUTION OF ALCOHOLS othe
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390 THE RESOLUTION OF ALCOHOLS proc
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392 THE RESOLUTION OF ALCOHOLS : or
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394 THE RESOLUTION OF ALCOHOLS are
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396 THE KE8QUJTIQN OF XWQT&QIS solu
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398 .THE RESOLUTION OF ALCOHOLS alc
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400 THE RESOLUTION OF ALCOHOLS The
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402 THE RESOLUTION OF ALCOHOLS slow
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404 THE RESOLUTION OF ALCOHOLS The
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406 THE RESOLUTION OF ALCOHOLS c7 c
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408 THE RESOLUTION OF ALCOHOLS Alco
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410 THE RESOLUTION OF ALCOHOLS CIO
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416 BART, BECHAMP, AND ROSENMUND RE
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432 BART, BECHAMP, AND BOSENMUND RE
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438 BART, BECHAMP, AND R08ENMUND RE
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\ 440 BART, BECHAMP, AND ROSENMUND
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442 BART, BECHAMP, ANP ROSENMUND RE
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448 BART, BECHAMP, AND R08ENMUND RE
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456 INDEX Amination of heterocyclic
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458 INDEX 1,2-Dibromofluoroethane,
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460 INDEX- ^-2-Naphthylpropionic ac
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Organic Reactions, Volume 2

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