Name Reactions: A Collection of Detailed Reaction MechanismsThe second edition includes five points of improvement: (a) Additional 16 name reactions have been supplemented; (b) I have corrected typos and a few dubious mechanisms in the first edition. I wish to thank Prof. Rick L. Danheiser of Massa chusetts Institute of Technology and Mr. Yiqian Lian of Michigan State Univer sity for invaluable comments and suggestions. I have also incurred many debts of gratitude to Prof. Brian. M. Stoltz of California Institute of Technology and his students, Eric Ashley, Doug Behenna, Dan Caspi, Neil Garg, Blake Greene, Jeremy May, Sarah Spessard, Uttam Tambar, Raissa Trend, and Ryan Zeidan for proofreading the final draft of the second edition; (c) The references are expanded and updated; (d) A more thorough index has been implemented so the reader may navigate through the book more easily; (e) The short descriptions of name reactions given as mnemonics seem to be helpful to both novices and veterans. As a result, I added the descriptions for most reactions. Finally, I am grateful for permission to use the postage stamps on the inner covers from respective postal authorities, who still retail the copyrights of those stamps. Jack Li Ann Arbor, Michigan, May 2003 Preface to the first edition What's in a name? That which we call a rose by any other name would smell as 1 sweet. |
Contents
Brown hydroboration reaction | 53 |
Bucherer carbazole synthesis | 54 |
Bucherer reaction | 56 |
BuchererBergs reaction | 57 |
BuchnerCurtiusSchlotterbeck reaction | 58 |
Buchner method of ring expansion | 59 |
BuchwaldHartwig CN bond and CO bond formation reactions | 60 |
Burgess dehydrating reagent | 61 |
Kumada crosscoupling reaction | 233 |
Larock indole synthesis | 235 |
Lawessons reagent | 236 |
LeuckartWallach reaction | 237 |
Lieben haloform reaction | 238 |
LiebeskindSrogl coupling | 239 |
Lossen rearrangement | 240 |
Luche reduction | 241 |
CadiotChodkiewicz coupling | 62 |
Cannizzaro dispropotionation reaction | 63 |
Carroll rearrangement | 65 |
CastroStephens coupling | 66 |
Chapman rearrangement | 67 |
Chichibabin amination reaction | 68 |
Chichibabin pyridine synthesis | 69 |
Chugaev reaction | 71 |
CiamicianDennsted rearrangement | 72 |
Claisen condensation | 73 |
Claisen rearrangement | 74 |
ClarkeEschweiler reductive alkylation of amines | 76 |
Clemmensen reduction | 77 |
Combes quinoline synthesis | 79 |
ConradLimpach reaction | 81 |
CookHeilbron thiazole synthesis | 82 |
Cope elimination reaction | 83 |
Cope oxyCope and anionic oxyCope rearrangements | 84 |
CoreyBakshiShibata CBS reduction | 86 |
CoreyChaykovsky reaction | 88 |
CoreyFuchs reaction | 90 |
CoreyKim oxidation | 92 |
CoreyWinter olefin synthesis | 93 |
Cornforth rearrangement | 95 |
Criegee glycol cleavage | 96 |
Criegee mechanism of ozonolysis | 97 |
Curtius rearrangement | 98 |
Dakin oxidation | 99 |
DakinWest reaction | 100 |
Danheiser annulation | 102 |
Darzens glycidic ester condensation | 103 |
Davis chiral oxaziridine reagent | 104 |
de Mayo reaction | 105 |
Demjanov rearrangement | 107 |
DessMartin periodinane oxidation | 109 |
Dieckmann condensation | 110 |
DielsAlder reaction | 111 |
Dienonephenol rearrangement | 113 |
Diлmethane rearrangement | 114 |
Doebner reaction | 115 |
Doebnervon Miller reaction | 117 |
DoeringLaFlamme allene synthesis | 119 |
DornowWiehler isoxazole synthesis | 120 |
Dötz reaction | 122 |
Dowd ring expansion | 123 |
DuttWormall reaction | 125 |
Eglinton reaction | 126 |
Eschenmoser coupling reaction | 127 |
EschenmoserTanabe fragmentation | 128 |
Étard reaction | 129 |
Evans aldol reaction | 130 |
Favorskii rearrangement and QuasiFavorskii rearrangement | 132 |
FeistBénary furan synthesis | 134 |
Ferrier rearrangement | 135 |
Finkelstein reaction | 136 |
FischerHepp rearrangement | 137 |
Fischer indole synthesis | 138 |
FischerSpeier esterification | 139 |
Fleming oxidation | 140 |
Forster reaction | 142 |
FraterSeebach alkylation | 144 |
FriedelCrafts reaction | 145 |
Friedländer synthesis | 147 |
Fries rearrangement | 149 |
FritschButtenbergWiechell rearrangement | 151 |
FujimotoBelleau reaction | 152 |
Fukuyama amine synthesis | 153 |
Gabriel synthesis | 155 |
Gassman indole synthesis | 156 |
GattermannKoch reaction | 157 |
Gewald aminothiophene synthesis | 158 |
Glaser coupling | 160 |
GombergBachmann reaction | 161 |
Gribble indole reduction | 162 |
Gribble reduction of diaryl ketones | 163 |
Grignard reaction | 164 |
Grob fragmentation | 166 |
GuareschiThorpe condensation | 168 |
HajosWiechert reaction | 169 |
HallerBauer reaction | 171 |
Hantzsch pyridine synthesis | 172 |
Hantzsch pyrrole synthesis | 174 |
Haworth reaction | 175 |
Hayashi rearrangement | 177 |
Heck reaction | 179 |
Hegedus indole synthesis | 181 |
HellVolhardtZelinsky reaction | 182 |
Henry reaction nitroaldol reaction | 183 |
Herz reaction | 184 |
Heteroaryl Heck reaction | 186 |
Hiyama crosscoupling reaction | 187 |
HochCampbell aziridine synthesis | 189 |
HodgesVedejs metallation of oxazoles | 191 |
Hofmann rearrangement Hofmann degradation reaction | 192 |
HofmannLöfflerFreytag reaction | 193 |
HofmannMartius reaction ReillyHickinbottom rearrangement | 194 |
Hooker oxidation | 196 |
HornerWadsworthEmmons reaction | 198 |
HoubenHoesch synthesis | 200 |
Hunsdiecker reaction | 202 |
IngManske procedure | 203 |
JacobsenKatsuki epoxidation | 204 |
Jacobsen rearrangement | 206 |
JappKlingemann hydrazone synthesis | 208 |
JuliaLythgoe olefination | 209 |
Kahne glycosidation | 211 |
Keck stereoselective allylation | 213 |
Keck macrolactonization | 215 |
Kemp elimination | 217 |
Kennedy oxidative cyclization | 218 |
Kharasch addition reaction | 219 |
Knöevenagel condensation | 220 |
Knorr pyrrole synthesis | 222 |
Koch carbonylation reaction KochHaaf carbonylation reaction | 223 |
KoenigKnorr glycosidation | 225 |
Kolbe electrolytic coupling | 226 |
KolbeSchmitt reaction | 227 |
Kostanecki reaction | 228 |
Krapcho decarboxylation | 230 |
Kröhnke reaction pyridine synthesis | 231 |
McFadyenStevens reduction | 242 |
McMurry coupling | 244 |
Madelung indole synthesis | 245 |
Mannich reaction | 246 |
Marshall boronate fragmentation | 248 |
Martins sulfurane dehydrating reagent | 249 |
MasamuneRoush conditions | 251 |
Meerwein arylation | 253 |
MeerweinPonndorfVerley reduction | 254 |
Meinwald rearrangement | 255 |
Meisenheimer complex | 256 |
Meisenheimer rearrangement | 258 |
MeyerSchuster rearrangement | 259 |
Michael addition | 260 |
MichaelisArbuzov phosphonate synthesis | 261 |
Midland reduction | 262 |
MillerLoudonSnyder nitrile synthesis | 263 |
MislowEvans rearrangement | 264 |
Mitsunobu reaction | 265 |
Miyaura boration reaction | 266 |
Moffatt oxidation | 267 |
MorganWalls reaction PictetHubert reaction | 269 |
MoriBan indole synthesis | 270 |
Morin rearrangement | 272 |
Mukaiyama aldol reaction | 274 |
Mukaiyama esterification | 275 |
MyersSaito cyclization | 277 |
Nametkin rearrangement retropinacol rearrangement | 279 |
Nazarov cyclization | 280 |
Neber rearrangement | 281 |
Nef reaction | 282 |
Negishi crosscoupling reaction | 283 |
Nenitzescu indole synthesis | 284 |
Nicholas reaction | 286 |
Noyori asymmetric hydrogenation | 287 |
NozakiHiyamaKishi reaction | 289 |
Oppenauer oxidation | 290 |
Orton rearrangement | 291 |
Overman rearrangement | 293 |
PaalKnorr furan synthesis | 294 |
PaalKnorr pyrrole synthesis | 295 |
Parham cyclization | 296 |
Passerini reaction | 298 |
PaternoBüchi reaction | 299 |
PausonKhand cyclopentenone synthesis | 300 |
Payne rearrangement | 302 |
Pechmann condensation coumarin synthesis | 303 |
Pechmann pyrazole synthesis | 304 |
Perkin reaction cinnamic acid synthesis | 305 |
Perkow vinyl phosphate synthesis | 307 |
Peterson olefination | 308 |
PfauPlattner azulene synthesis | 310 |
Pfitzinger quinoline synthesis | 311 |
PictetGams isoquinoline synthesis | 312 |
PictetSpengler tetrahydroisoquinoline synthesis | 314 |
Pinacol rearrangement | 315 |
Pinner synthesis | 316 |
Polonovski reaction | 317 |
PolonovskiPotier rearrangement | 319 |
PomeranzFritsch reaction | 320 |
Prévost transdihydroxylation | 322 |
Prilezhaev reaction | 323 |
Prins reaction | 324 |
Pschorr ring closure | 325 |
Pummerer rearrangement | 327 |
RambergBäcklund olefin synthesis | 328 |
Reformatsky reaction | 329 |
Regitz diazo synthesis | 330 |
ReimerTiemann reaction | 332 |
Reissert reaction aldehyde synthesis | 334 |
Riley oxidation selenium dioxide oxidation | 336 |
Ringclosing metathesis RCM using Grubbs and Schrock catalysts | 337 |
Ritter reaction | 339 |
Robinson annulation | 340 |
RobinsonSchöpf reaction | 341 |
Rosenmund reduction | 343 |
Roush allylboronate reagent | 344 |
Rubottom oxidation | 345 |
Rupe rearrangement | 346 |
Rychnovsky polyol synthesis | 347 |
Sakurai allylation reaction HosomiSakurai reaction | 349 |
Sandmeyer reaction | 351 |
Sarett oxidation | 352 |
Schiemann reaction BalzSchiemann reaction | 354 |
Schlosser modification of the Wittig reaction | 355 |
Schmidt reaction | 356 |
Schmidts trichloroacetimidate glycosidation reaction | 357 |
Scholl reaction | 359 |
Schöpf reaction | 361 |
SchottenBaumann reaction | 362 |
Shapiro reaction | 363 |
Sharpless asymmetric amino hydroxylation | 364 |
Sharpless asymmetric epoxidation | 366 |
276 | 375 |
280 | 381 |
284 | 387 |
288 | 393 |
293 | 399 |
297 | 405 |
301 | 411 |
418 | |
424 | |
431 | |
437 | |
438 | |
439 | |
440 | |
441 | |
443 | |
444 | |
445 | |
446 | |
447 | |
Yamaguchi esterification | 448 |
450 | |
Zincke reaction | 451 |
Zinin benzidine rearrangement semidine rearrangement | 453 |
455 | |
460 | |
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Common terms and phrases
acid acyl addition AICI3 alcohols aldehydes aldol alkyl amine Angew Asymmetric Bull carbonyl carbonyl compounds catalytic cycle CCl3 CH3O Chem Chim CO₂ CO₂CH3 CO₂Et CO₂Et CO₂Et CO₂H CO₂Me CO₂R³ Commun Comprehensive Organic Synthesis condensation cross-coupling reaction cyclization cycloaddition Dtsch enamine Engl enolate EtO2C formation Grignard reagents H R¹ H References H+ H H+ OH H₂N H₂O Heterocycl hydrolysis intermediate Justus Liebigs Justus Liebigs Ann ketones M. J. Chem Michael addition N₂ NH₂ nucleophilic O₂N OH OH OH₂ olefins OR¹ OR² Organic Synthesis Organomet oxidation Perkin Trans Ph Ph Pharm PPh3 Prep R¹ H R¹ R¹ R¹ R² R¹O R² H R² R¹ React reagent rearrangement Reddy reductive Review Sharpless Synlett Synth Synthesis 2002 Tetrahedron 1998 Tetrahedron 2000 Tetrahedron Lett transmetallation Wang workup ylide