Named Organic Reactions
Thomas Laue and Andreas Piagens
Technical University, Braunschweig, Germany
Translated into English by Dr. Claus Vogel Universität Magdeburg, Germany
JOHN WILEY & SONS Chichester • New York • Weinheim • Brisbane • Singapore • Toronto Contents
Introduction ix Acyloin Ester Condensation 1 Aldol Reaction 4 Alkene Metathesis 10 Arbuzov Reaction 12 Arndt-Eistert Synthesis 13 Baeyer-Villiger Oxidation 16 Bamford-Stevens Reaction 19 Beckmann Rearrangement 22 Benzidine Rearrangement 24 Benzilic Acid Rearrangement 26 Benzoin Condensation 27 Bergman Cyclization 29 Birch Reduction 33 Blanc Reaction 36 Bucherer Reaction 37 Cannizzaro Reaction 40 Chugaev Reaction 42 Claisen Ester Condensation 45 Claisen Rearrangement 48 Clemmensen Reduction 52 Cope Elimination Reaction 54 Cope Rearrangement 56 Corey-Winter Fragmentation 59 Curtius Reaction 61 1,3-Dipolar Cycloaddition 64 [2 + 2] Cycloaddition 67 Darzens Glycidic Ester Condensation 71 Delepine Reaction 73 Diazo Coupling 74 Diazotization 77 Diels-Alder Reaction 78 vi Contents
Di-7r-Methane Rearrangement 86 Dötz Reaction 88 Elbs Reaction 92 Ene Reaction 93 Ester Pyrolysis 97 Favorskii Rearrangement 100 Finkelstein Reaction 102 Fischer Indole Synthesis 103 Friedel-Crafts Acylation 106 Friedel-Crafts Alkylation 110 Friedländer Quinoline Synthesis 114 Fries Rearrangement 116 Gabriel Synthesis 120 Gattermann Synthesis 123 Glaser Coupling Reaction 125 Glycol Cleavage 127 Gomberg-B achmann Reaction 129 Grignard Reaction 132 Haloform Reaction 139 Hantzsch Pyridine Synthesis 141 Heck Reaction 144 Hell-Volhard-Zelinskii Reaction 147 Hofmann Elimination Reaction 149 Hofmann Rearrangement 153 Hunsdiecker Reaction 155 Hydroboration 157 Japp-Klingemann Reaction 161 Knoevenagel Reaction 164 Knorr Pyrrole Synthesis 168 Kolbe Electrolytic Synthesis 170 Kolbe Synthesis of Nitriles 172 Kolbe-Schmitt Reaction 173 Leuckart-Wallach Reaction 175 Lossen Reaction 176 Malonic Ester Synthesis 178 Mannich Reaction 182 McMurry Reaction 184 Contents vii
Meerwein-Ponndorf-Verley Reduction 187 Michael Reaction 189 Mitsunobu Reaction 192 Nazarov Cyclization 195 Neber Rearrangement 197 Nef Reaction 198 Norrish Type I Reaction 200 Norrish Type II Reaction 203 Ozonolysis 206 Paterno-Büchi Reaction 209 Pauson-Khand Reaction 210 Perkin Reaction 213 Peterson Olefination 215 Pinacol Rearrangement 217 Prilezhaev Reaction 218 Prins Reaction 220 Ramberg-Bäcklund Reaction 223 Reformatsky Reaction 224 Reimer-Tiemann Reaction 226 Robinson Annulation 228 Rosenmund Reduction 232 Sakurai Reaction 234 Sandmeyer Reaction 236 Schiemann Reaction 237 Schmidt Reaction 239 Sharpless Epoxidation 242 Simmons-Smith Reaction 244 Skraup Quinoline Synthesis 246 Stevens Rearrangement 248 Stork Enamine Reaction 250 Strecker Synthesis 253 Tiffeneau-Demjanov Reaction 255 Vilsmeier Reaction 258 Vinylcyclopropane Rearrangement 260 Wagner-Meerwein Rearrangement 263 Weiss Reaction 265 Willgerodt Reaction 267 viii Contents
Williamson Ether Synthesis 269 Wittig Reaction 271 Wittig Rearrangement 275 Wohl-Ziegler Bromination 277 Wolff Rearrangement 279 Wolff-Kishner Reduction 281 Wurtz Reaction 282 Index 285