Weygand/Hilgetag Preparative Organic Chemistry

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CONTRIBUTING AUTHORS CH. BISCHOFF (BERLIN) P.-G. DIETRICH (BERLIN) I. EICHHORN (BERLIN) E. GRUNDEMANN (BERLIN) E. HOFT (BERLIN) G. LEHMANN (BERLIN) D. MURAWSKI (BERLIN) E. SCHMITZ (BERLIN) H. SEEBOTH (BERLIN) J. DAHLMANN (BERLIN) H. DORN (BERLIN) H. GROSS (BERLIN) G. HILGETAG (BERLIN) O. KOVACS (SZEGED) D. MARTIN (BERLIN) R. OHME (BERLIN) H. SCHICK (BERLIN) M. SCHULZ (BERLIN) H. TEICHMANN (BERLIN) A. ZUBEK (BERLIN)
WEYGAND/HILGETAG PREPARATIVE ORGANIC CHEMISTRY EDITED BY G. HILGETAG AND A. MARTINI Institut fur Organische Chemie der Deutschen Akademie der Wissenschaften zu Berlin A Wiley-Inter science Publication JOHN WILEY & SONS New York • London • Sydney • Toronto
Page 1: PREPARATIVE ORGANIC CHEMISTRY
Page 5 and 6: Foreword to the 4 th Edition The fi
Page 7: Summary of Contents Introduction: O
Page 10 and 11: X Contents II. Addition of hydrogen
Page 12 and 13: x ii Contents II. Replacement of ha
Page 14 and 15: xiv Contents II. Esters 368 1. Repl
Page 16 and 17: xvi Contents 1. Replacement of nitr
Page 18 and 19: xviii Contents 5. Cleavage of the S
Page 20 and 21: xx Contents Chapter 11. Formation o
Page 22 and 23: xxii Contents 1.3. Formation of new
Page 24 and 25: xxiv Contents IV. Rearrangement of
Page 27 and 28: Introduction: Organization of the M
Page 29: PART A Reactions on the Intact Carb
Page 32 and 33: 6 Formation of carbon-hydrogen bond
Page 34 and 35: 8 Formation of carbon-hydrogen bond
Page 36 and 37: 10 Formation of carbon-hydrogen bon
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26 Formation of carbon-hydrogen bon
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86 Formation of carbon-deuterium bo
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100 Formation of carbon-deuterium b
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CHAPTER 3 Formation of Carbon-Halog
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104 Formation of carbon-halogen bon
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240 Formation of c arbon-halogen bo
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274 Formation of carbon-oxygen bond
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392 Cleavage of carbon-oxygen bonds
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CHAPTER 6 Formation of Carbon-Nitro
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406 Formation of carbon-nitrogen bo
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48 8 Formation of carbon-nitrogen b
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550 Alteration of nitrogen groups i
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CHAPTER 8 Formation of Carbon-Sulfu
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602 Formation of carbon-sulfur bond
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694 Formation of carbon-phosphorus
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CHAPTER 10 Formation of Metal-Carbo
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750 Formation of metal-carbon bonds
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7 52 Formation of metal-carbon bond
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814 Formation of carbon-carbon mult
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PARTB Formation of new carbon-carbo
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Addition to C=C bonds 847 Under the
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Addition to C= C bonds 849 A radica
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Addition to C=C bonds 851 ful catal
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formation (b) that is necessary for
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Addition to C —C bonds 855 Nitril
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Addition to C —C bonds 857 3,6-ep
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Addition to C—C bonds 8 59 Stereo
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Addition to C=C bonds 861 6. Additi
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Addition to C=C bonds 863 In this c
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Addition to C=C bonds 865 are added
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Addition to C=C bonds 867 amount of
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Addition to the C=O bond 869 Such a
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Addition to the C=O bond 871 Such c
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Addition to the C=O bond 873 3. For
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Addition to the C=O bond 875 In hyd
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Addition to the C=O bond 877 Finely
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Addition to the C=O bond 879 the te
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Addition to the C=O bond 881 A Grig
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Addition to the C=O bond 883 c. Tre
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Addition to the C= O bond 885 The d
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Addition to C-N multiple bonds 887
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C-C linkage by removal of hydrogen
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C~C linkage by removal of hydrogen
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C-C linkage by replacement of halog
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esters: 634 ' 640 ' 641 C-C linkage
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C-C linkage by replacement of hydro
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C-C linkage by replacement of OR by
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C-C linkage by replacement of O-acy
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C-C linkage by replacement of nitro
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tions (see also page 957): C-C link
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Removal of halogen with formation o
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Formation of a new C=C bond by remo
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Removal of sulfur with formation of
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Removal of phosphorus with formatio
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Removal of phosphorus with formatio
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PART C Cleavage of Carbon-Carbon Bo
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Removal of carbon dioxide 1005 Only
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Removal of carbon dioxide 1007 resp
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Removal of carbon dioxide 1009 e. N
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Removal of carbon dioxide 1011 Hydr
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Removal of carbon d ioxide 1013 Thi
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Removal of carbon d ioxide 1015 as
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Removal of carbon dioxide 1017 char
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Removal of carbon dioxide 1019 Conv
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Removal of carbon monoxide 1021 Thi
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Removal of carbon monoxide 1023 lab
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Removal of carbon monoxide 1025 It
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Removal of other fragments 1027 1.
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Removal of other fragments 1029 sol
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Removal of other fragments 1031 The
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Oxidative cleavage of C-C bonds in
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Oxidative degradation of olefins 10
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Oxidative cleavage of carbon-carbon
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Oxidative cleavage of carbon-carbon
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Oxidative degradation of aromatic a
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Hydrolytic cleavage 1047 Cleavage b
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Hydrolytic cleavage 1049 Ethyl acet
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PART D Rearrangements of Carbon Com
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Migration of a multiple bond 1055 i
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Migration of a multiple bond 1057 A
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Rearrangement with change of an oxy
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2 hours at 250-270°, thus: 54 Rear
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Rearrangement of halogen compounds
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Migration from oxygen to carbon 106
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Migration from oxygen to carbon 107
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Migration from nitrogen to carbon 1
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Benzyl-0-tolyl rearrangement 1075 R
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Migration from carbon to nitrogen 1
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Wagner-Meerwein rearrangement and r
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Wagner-Meerwein rearrangement and r
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Cope rearrangement; valence isomeri
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Cope rearrangement; valence isomeri
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Rearrangement on decomposition of d
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Rearrangement on decomposition of d
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Appendix I Purification and drying
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Purification and drying of organic
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Preparation and purification of gas
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Preparation and purification of gas
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Preparative organic work with small
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SUBJECT INDEX This index deals prim
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Acetophenone, co-amino-, 451 —, b
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Aldehyde nitrates, 423 Aldehydes, a
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Amidic acids, 485 Amidines, 472 —
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Aporphine, 970 D-Arabinose, 1029
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Benzene, pentaphenyl-, 831 — ,pen
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Benzoyl chloride, 246 — —, 0-ch
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Butane, l-bromo-4-chloro-, 238 —,
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Carbodiimide, dicyclohexyl-, oxidat
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Chloromethylation, 158, 952 (Chloro
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Cyclohexanone, 2,3-epoxy-3,5,5-trim
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Diethyl ether, sulfide, 637, 653
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Ethane, 1,2-dichloro-, 107 —, 1 ,
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Formic acid, esters, decomposition,
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Heptatrienal, 7-phenyl-, 988 3-Hept
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Hydroquinones, 0-mercapto, 606 Hydr
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Ketones, (x,oc-dibromo, 191, 258
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Methane, diphenyltolyl-, 949 —, n
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l-Naphthylamines, JV-aryl-, 531, 53
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Oxazole, 5-ethoxy-2-phenyl-, 858 Ox
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Phenyl azide, 584 — isocyanate, 4
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Propane, l,2,3-trichloro-2-methyl-,
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2,6-Pyridinediamine, 443 3,5-Pyridi
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Silane, trichloro(chloromethyl)-, 7
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Sulfoxides, 630, 667, 668 —, redu
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Thiouronium salts, 692 , S-cyclohex
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Valence isomerization, 1088 Valeral
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