Organic Reactions, Volume 2

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Compound Ethyl O-allylacetoacetate " Ethyl O-cinnamylacetoacetate O-Allylacetylacetone O-AHyloxymethylenecamphor Allyl vinyl ether Allyl a-methylvinyl ether Allyl ot-phenylvinyl ether 7-Ethylallyl vinyl ether containing 23% of a-isomer Aryl Group in ArOCH2CH=CH2 2-Propenyl-4-propyl-6-methoxyphenyl 2-Propenyl-4,6-dichlorophenyl 2-Propenyl-4,6-dimethylphenyl * References 104-129 appear on p 48. B- TABLE I. REARRANGEMENT OV OPEN-CHAIN COMPOUNDS Time, hours — 4 6 — — — 1 1 Conditions; Temperature, ° C. 150-200 110 260 — At b.p. 255 255
None Ring Substituents in OHo-sCHOHoOr" Hi; 2-Methyl 3-MethyI 4-Methyl ' 2-Hydroxymethyl 2-Allyl 2,4-DimethyI 3,5-Dimethyl 2-Allyl-3-(and -5-) methyl f 2-Allyl-4-methyl 2-Propyl-4-methyl Time, hours Several 1.3 1 13 0.5 3 — — "Long refluxing" 11 TABLE II ortho REARRANGEMENTS OF ALLYL ABTL ETHEBS A. Benzene Derivatives Conditions Temperature, °C. 190-220 207-231 210-240 200 — 237 200-210 — 230-270 — 230-252 Solvent (or Other Special Condition) (Inert atmosphere) — — (Inert atmosphere) — Diethylaniline (Inert atmosphere) — — — (Inert atmosphere) 2-Allyl (dimer) Product Substituents in Phenolic Ring 6-Allyl-2-methyl 2-Allyl-3-methyl, 6-Allyl-3-methyl 2-Allyl-4-methyl (CH2O, decomposition products) 2,6-DialIyl 6-Allyl-2,4-dimethyl 2-Allyl-3,5-dimethyl , 2,6-Diallyl-3-methyl 2,6-Diallyl-4-methyl 6-Allyl-2-propyl-4-methyl (2-Propyl-4-methyl-phenol) • Yield ">85% 78% 70% >85% — - 80% >85% — 30% 10% 67% 10% Reference * 11 (p. 79), 27, 28, 29,60 44 (p. 56) 44 (p. 58) 44 (p. 43), 34,67 44 (p. 106) 11 (p. 91) 26, 104 105 44 (p. 58) 44 (p. 45) 34 o i IM
Page 1 and 2: Organic Reactions VOLUME II EDITORI
Page 3 and 4: PREFACE TO THE SERIES In the course
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: 28 THE CLAISEN REARRANGEMENT pressu
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
Page 53 and 54: 48 THE CLAISEN REARRANGEMENT 104 Ki
Page 55 and 56: 50 ALIPHATIC FLUORINE COMPOUNDS ^~
Page 57 and 58: 52 ALIPHATIC FLUORINE COMPOUNDS ace
Page 59 and 60: 64 ALIPHATIC FLUORINE COMPOUNDS of
Page 61 and 62: 56 ALIPHATIC FLUORINE COMPOUNDS Fro
Page 63 and 64: 58 ALIPHATIC FLUORINE COMPOUNDS pro
Page 65 and 66: 60 ALIPHATIC FLUORINE COMPOUNDS Rea
Page 67 and 68: 62 ALIPHATIC FLUORINE COMPOUNDS rem
Page 69 and 70: 64 - ALIPHATIC FLUORINE COMPOUNDS m
Page 71 and 72: 66 ALIPHATIC FLUORINE COMPOUNDS com
Page 73 and 74: 68 ALIPHATIC FLUORINE COMPOUNDS to
Page 75 and 76: 70 t ALIPHATIC FLUORINE COMPOUNDS t
Page 77 and 78: 72 ALIPHATIC FLUORINE COMPOUNDS flu
Page 79 and 80: 74 ALIPHATIC FLUORINE COMPOUNDS men
Page 81 and 82: (CF)* CFBr3 CFCI3 CFN CF2Br2 CF2C12
Page 83 and 84: 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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