Named Organic Reactions 2nd Edition Thomas Laue and Andreas Plagens

Named Organic Reactions 2nd Edition

Thomas Laue and Andreas Plagens

Named Organic Reactions 2nd Edition Thomas Laue and Andreas Plagens

Named reactions still are an important element of organic chemistry, and a thorough knowledge of such reactions is essential for the chemist. The scientific content behind the name is of great importance, and the names themselves are used as short expressions in order to ease spoken as well as written communication in organic chemistry. Furthermore, named reactions are a perfect aid for learning the principles of organic chemistry. This is not only true for the study of chemistry as a major subject, but also when studying chemistry as a minor subject, e.g. for students of biology or pharmaceutics. This book—Named Organic Reactions—is not meant to completely replace an organic chemistry textbook. It is rather a reference work on named reactions, which will also be suitable for easy reading and learning, as well as for revision for an exam in organic chemistry. This book deals with about 135 of the most important reactions in organic chemistry; the selection is based on their importance for modern preparative organic chemistry, as well as a modern organic

chemistry course. In particular, the reactions are arranged in alphabetical order, and treated in a

consistent manner. The name of the reaction serves as a heading, while a subtitle gives a one sentence-description of the reaction. This is followed by a formula scheme depicting the overall reaction and a first paragraph with an introductory description of the reaction. The major part of each chapter deals with mechanistic aspects; however, for didactic reasons, in most cases not with too much detail. Side-reactions, variants and modified procedures with respect to product distribution and yields are described. Recent, as well as older examples for the application of a particular reaction or method are given, together with references to the original literature. These examples are not aimed at a complete treatment of every aspect of a particular reaction, but are rather drawn from a didactic point of view. At the end of each chapter, a list of references is given. In addition to the very

first publication, and to review articles, references to recent and very recent publications are often given. This is meant to encourage work with, and to give access to the original literature, review articles and reference works for a particular reaction. The reference to the very first publication on a reaction is aimed at the origin of the particular name, and how the reaction was explored or developed. With x Introduction to the 2nd Edition the outlining of modern examples and listing of references, this book is directed at the advanced student as well as doctoral candidates. Special thanks go to Prof. Dr. H. Hopf (University of Braunschweig, Germany) for his encouragement and his critical reading of the manuscript. In addition, we are indebted to Dr. Claus Vogel and Heike Laue, as well as to those people who have helped us with suggestions to improve the text and keep it up-to-date.

Contents
Introduction to the 2nd Edition ix
Acyloin Ester Condensation 1
Aldol Reaction 4
Alkene Metathesis 10
Arbuzov Reaction 14
Arndt–Eistert Synthesis 16
Baeyer–Villiger Oxidation 19
Bamford–Stevens Reaction 22
Barton Reaction 25
Baylis–Hillman Reaction 28
Beckmann Rearrangement 31
Benzidine Rearrangement 33
Benzilic Acid Rearrangement 35
Benzoin Condensation 36
Bergman Cyclization 39
Birch Reduction 43
Blanc Reaction 45
Bucherer Reaction 47
Cannizzaro Reaction 50
Chugaev Reaction 52
Claisen Ester Condensation 55
Claisen Rearrangement 58
Clemmensen Reduction 62
Cope Elimination Reaction 64
Cope Rearrangement 66
Corey–Winter Fragmentation 69
Curtius Reaction 71
1,3-Dipolar Cycloaddition 74
[2Y2 ] Cycloaddition 77
Darzens Glycidic Ester Condensation 81
Del´epine Reaction 83
Diazo Coupling 84
Diazotization 87
Diels–Alder Reaction 88
Di-p-Methane Rearrangement 96
vi Contents
D¨otz Reaction 98
Elbs Reaction 102
Ene Reaction 103
Ester Pyrolysis 107
Favorskii Rearrangement 110
Finkelstein Reaction 112
Fischer Indole Synthesis 113
Friedel–Crafts Acylation 116
Friedel–Crafts Alkylation 120
Friedl¨ander Quinoline Synthesis 124
Fries Rearrangement 126

Gabriel Synthesis 130
Gattermann Synthesis 133
Glaser Coupling Reaction 135
Glycol Cleavage 137
Gomberg–Bachmann Reaction 139
Grignard Reaction 142
Haloform Reaction 149
Hantzsch Pyridine Synthesis 151
Heck Reaction 154
Hell–Volhard–Zelinskii Reaction 159
Hofmann Elimination Reaction 161
Hofmann Rearrangement 166
Hunsdiecker Reaction 167
Hydroboration 169
Japp-Klingemann Reaction 173
Knoevenagel Reaction 176
Knorr Pyrrole Synthesis 180
Kolbe Electrolytic Synthesis 182
Kolbe Synthesis of Nitriles 184
Kolbe–Schmitt Reaction 185
Leuckart–Wallach Reaction 187
Lossen Reaction 188
Malonic Ester Synthesis 190
Mannich Reaction 194
McMurry Reaction 196
Meerwein–Ponndorf–Verley Reduction 199
Michael Reaction 201
Mitsunobu Reaction 204
Nazarov Cyclization 207
Neber Rearrangement 209
Nef Reaction 210
Contents vii
Norrish Type I Reaction 212
Norrish Type II Reaction 215
Ozonolysis 218
Paterno–B¨uchi Reaction 221
Pauson–Khand Reaction 222
Perkin Reaction 225
Peterson Olefination 227
Pinacol Rearrangement 229
Prilezhaev Reaction 230
Prins Reaction 232
Ramberg–B¨acklund Reaction 235
Reformatsky Reaction 236
Reimer–Tiemann Reaction 238
Robinson Annulation 240
Rosenmund Reduction 244
Sakurai Reaction 246
Sandmeyer Reaction 248
Schiemann Reaction 249
Schmidt Reaction 251
Sharpless Epoxidation 254
Simmons–Smith Reaction 258
Skraup Quinoline Synthesis 260
Stevens Rearrangement 262
Stille Coupling Reaction 264
Stork Enamine Reaction 267
Strecker Synthesis 270
Suzuki Reaction 271
Swern Oxidation 274
Tiffeneau–Demjanov Reaction 277
Vilsmeier Reaction 280
Vinylcyclopropane Rearrangement 282
Wagner–Meerwein Rearrangement 285
Weiss Reaction 287
Willgerodt Reaction 289
Williamson Ether Synthesis 291
Wittig Reaction 293
Wittig Rearrangement 297
Wohl–Ziegler Bromination 299
Wolff Rearrangement 301
Wolff–Kishner Reduction 303
Wurtz Reaction 304

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