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Science of Synthesis provides a critical review of the synthetic methodology developed from the early 1800s to date for the entire field of organic and organometallic chemistry. As the only resource providing full-text descriptions of organic transformations and synthetic methods as well as experimental procedures, Science of Synthesis is therefore a unique chemical information tool.
Over 1000 world-renowned experts have chosen the most important molecular transformations for a class of organic compounds and elaborated on their scope and limitations. The systematic, logical and consistent organization of the synthetic methods for each functional group enables users to quickly find out which methods are useful for a particular synthesis and which are not. Effective and practical experimental procedures can be implemented quickly and easily in the lab.
The content of this e-book was originally published in December 2009.
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Veröffentlichungsjahr: 2013
Science of Synthesis is the authoritative and comprehensive reference work for the entire field of organic and organometallic synthesis.
Science of Synthesis presents the important synthetic methods for all classes of compounds and includes:
Methods critically evaluated by leading scientists
Background information and detailed experimental procedures
Schemes and tables which illustrate the reaction scope
As our understanding of the natural world increases, we begin to understand complex phenomena at molecular levels. This level of understanding allows for the design of molecular entities for functions ranging from material science to biology. Such design requires synthesis and, as the structures increase in complexity as a necessity for specificity, puts increasing demands on the level of sophistication of the synthetic methods. Such needs stimulate the improvement of existing methods and, more importantly, the development of new methods. As scientists confront the synthetic problems posed by the molecular targets, they require access to a source of reliable synthetic information. Thus, the need for a new, comprehensive, and critical treatment of synthetic chemistry has become apparent. To meet this challenge, an entirely new edition of the esteemed reference work Houben–Weyl Methods of Organic Chemistry will be published starting in the year 2000.
To reflect the new broader need and focus, this new edition has a new title, Science of Synthesis, Houben–Weyl Methods of Molecular Transformations. Science of Synthesis will benefit from more than 90 years of experience and will continue the tradition of excellence in publishing synthetic chemistry reference works. Science of Synthesis will be a balanced and critical reference work produced by the collaborative efforts of chemists, from both industry and academia, selected by the editorial board. All published results from journals, books, and patent literature from the early 1800s until the year of publication will be considered by our authors, who are among the leading experts in their field. The 48 volumes of Science of Synthesis will provide chemists with the most reliable methods to solve their synthesis problems. Science of Synthesis will be updated periodically and will become a prime source of information for chemists in the 21st century.
Science of Synthesis will be organized in a logical hierarchical system based on the target molecule to be synthesized. The critical coverage of methods will be supported by information intended to help the user choose the most suitable method for their application, thus providing a strong foundation from which to develop a successful synthetic route. Within each category of product, illuminating background information such as history, nomenclature, structure, stability, reactivity, properties, safety, and environmental aspects will be discussed along with a detailed selection of reliable methods. Each method and variation will be accompanied by reaction schemes, tables of examples, experimental procedures, and a background discussion of the scope and limitations of the reaction described.
The policy of the editorial board is to make Science of Synthesis the ultimate tool for the synthetic chemist in the 21st century.
We would like to thank all of our authors for submitting contributions of such outstanding quality, and, also for the dedication and commitment they have shown throughout the entire editorial process.
The Editorial Board
October 2000
D. Bellus (Basel, Switzerland)
E. N. Jacobsen (Cambridge, USA)
S. V. Ley (Cambridge, UK)
R. Noyori (Nagoya, Japan)
M. Regitz (Kaiserslautern, Germany)
P. J. Reider (New Jersey, USA)
E. Schaumann (Clausthal-Zellerfeld, Germany)
I. Shinkai (Tsukuba, Japan)
E. J. Thomas (Manchester, UK)
B. M. Trost (Stanford, USA)
Preface
Product Class Overview
Structure Index
Name Reaction Index
Keyword Index
Author Index
Erratum
Abbreviations
This index comprises a list of key cyclic substructures present in the products of Category 6 (Compounds with All-Carbon Functions).
To use this index you first need to identify the following four characteristics for the ring system you are interested in:
whether the system is monocyclic, bicyclic, etc. (see page header)
the ring size, i.e. three membered, four membered, etc. (see left-hand column)
the number of heteroatoms within the ring system (see left-hand column)
heteroatoms are prioritized in the following order:
main-group elements: (O, S, Se, Te, N, P, As, Sb, Bi)
main-group metals: (Si, Ge, Sn, Pb, B, Al, Ga, In, Tl, Mg)
transition, lanthanide, and actinide metals
Having identified the ring system of interest, please refer to the number beneath the structure in order to determine the relevant volume number (small and bold) and page number within the series.
A
Acyloin condensation
– Acyloin condensation 45b-1299, 1314
Adams’ catalyst
– Adams’ catalyst 48-265, 282, 288, 306–308
Alder rule
– Alder rule 47b-566
Alder-ene reaction
–Alder-ene reaction 46-227
Alder–Stein principle
– Alder–Stein cis-principle 47b-569
Aldol condensation
– Aldol condensation 45b-896, 898, 899, 1315
Aldol reaction
– Aldol adduct 46-157
– Aldol condensation 43-462, 46-8, 148–150, 161
– Aldol reaction 44-206, 337, 45b-755, 46-6, 7, 147, 150, 332, 47a-32, 48-671, 672
– Aldol reaction, vinylogous 46-153
– Aldol trimerization 45b-1164–1166
– Aldol-type condensation 43-454
– Aldol-type reaction 46-153
– Iodo-aldol carbocyclization 48-669
– Retro-aldol reaction 47a-132, 149
– Retro-aldol-type reaction 47a-109, 145
Alpine borane
– Alpine borane 44-89, 90
Ando method
– Ando modification of the Horner–Wadsworth–Emmons reaction 46-278
– Ando variation of the Horner–Wadsworth–Emmons reaction 46-42
Angeli's salt
– Angeli's salt 46-435
Appel reaction
– Appel reaction 43-6
Arbuzov reaction
– Arbuzov reaction 45a-212, 47a-66
B
Baeyer's synthesis
– Baeyer's indigo synthesis 43-39
– Baeyer's preparation 43-39
Baeyer–Villiger oxidation
– Baeyer–Villiger oxidation 45a-306
Bamford–Stevens reaction
– Bamford–Stevens conditions 47b-860
– Bamford–Stevens methodology 47b-858
– Bamford–Stevens reaction 43-651, 47a-5, 8, 47b-841, 853–858, 860
Barbier reaction
– Barbier reaction 48-686
– Barbier-type conditions 45a-219, 220, 47a-144, 152, 155, 156
– Barbier-type protocol 47a-144
– Barbier-type reaction 47b-1103
Barbier–Grignard reaction
– Barbier–Grignard protocol 43-635
– Barbier–Grignard reaction 43-635
Barton reaction
– Barton reductive decarboxylation 48-452
– Wolff–Kishner reduction, Barton conditions 48-118
– Wolff–Kishner reduction, Barton modification 48-112, 117
Barton–McCombie reaction
– Barton–McCombie-based elimination 47a-135, 136
– Barton–McCombie deoxygenation 47a-135, 48-4, 175, 190, 191, 258
– Barton–McCombie hydroxy-group removal 48-5
– Barton–McCombie procedure 48-193
– Barton–McCombie reaction 48-139, 164, 175, 190–195, 232, 258
Baylis–Hillman reaction
– Aza-Baylis–Hillman product 44-303
– Baylis–Hillman adduct 47a-527
– Baylis–Hillman derived bromides 47a-509
– Baylis–Hillman nitrile 47a-527
– Baylis–Hillman reaction 44-377
– Baylis–Hillman style 44-203
– Baylis–Hillman-type reaction 44-204
Becker–Alder oxidation
– Becker–Alder oxidation 46-608
Beckmann rearrangement
– Beckmann rearrangement 45a-306
Benkeser reduction
– Benkeser reduction 47b-1153, 1154
Bergman reaction
– Bergman cyclization 43-152, 215–218, 291, 345
– Bergman reaction 43-152
– Bergman-type cyclization 43-215, 268
– Retro-Bergman reaction 43-213
Bergman rearrangement
– Bergman cyclization 45b-768, 792, 793, 799, 800
– Bergman cycloaromatization 45b-839
– Bergman rearrangement 45b-768, 769
Bestmann–Ohira reaction
– Bestmann–Ohira alkynylation 43-19, 384
– Bestmann–Ohira method 43-18
– Bestmann–Ohira modification 43-383
– Bestmann–Ohira reaction 43-24, 480
– Bestmann–Ohira reagent 43-18, 382, 383f., 456f., 458, 459f.
Bingel reaction
– Bingel reaction 45b-1130
Birch reduction
– Birch conditions 45b-1168
– Birch reduction 45a-343, 45b-1060, 46-18, 543, 544, 47a-8, 1017, 1018, 1153, 1154, 48-653
– Birch-type reduction 47a-6, 8
Blechert's catalyst
– Blechert's catalyst 45b-915, 917
Borch reagent
– Borch reagent 45b-1307
Bredt rule
– Anti-Bredt derivative 47b-886
Breslow reaction
– Breslow conditions 43-123, 126
– Breslow's modification 43-405, 412, 414, 418
– Breslow's procedure 43-123
Brewster–Lowe rule
– Brewster–Lowe rule 44-74
Britzinger's compound
– Britzinger's compound 48-412
Brønstedt acid
– Brønstedt acid 45a-161, 46-448–450, 469, 481, 653, 47b-671, 675–678, 1077, 48-403
– Brønstedt acid/base system 47a-52
– Brønstedt acidic conditions 47b-1078
– Brønstedt acidity 45a-161
Brook rearrangement
– 1,4-Brook rearrangement 48-665
– Brook rearrangement 43-525, 44-358
– Chromium Brook rearrangement 45b-1365
– Retro-Brook rearrangement 44-377
– Tandem Brook rearrangement 43-525, 527
Buchner reaction
– Buchner reaction 45a-330
Buchner reaction
– Buchner reaction 45b-1060, 1086, 1405, 1406
Burgess reagent
– Burgess reagent 46-450–452, 508
C
Cadiot–Chodkiewicz coupling
– Cadiot–Chodkiewicz conditions 43-54
– Cadiot–Chodkiewicz conditions, modified 43-131, 419
– Cadiot–Chodkiewicz coupling 43-5, 51–55, 64, 92, 95, 130, 261, 444
– Cadiot–Chodkiewicz coupling, secondary 43-52
– Cadiot–Chodkiewicz cross coupling 43-24, 52, 91, 130
– Cadiot–Chodkiewicz heterocoupling 43-7, 51–53
– Cadiot–Chodkiewicz reaction 43-51, 62, 92f., 261, 325, 47b-951
– Cadiot–Chodkiewicz-type coupling 43-67
– Cadiot–Chodkiewicz-type cross coupling 43-556
– Cadiot–Chodkiewicz-type heterocoupling 43-55, 58
– Chodkiewicz conditions 43-91
Cannizzaro reaction
– Cannizzaro reaction 47a-32
Carreira's reaction
– Carreira's alkynylation 44-92
Carroll rearrangement
– Carroll rearrangement 43-269
Chatgilialoglu's reagent
– Chatgilialoglu's reagent 44-199
Chugaev reaction
– Chugaev elimination 48-193
– Chugaev method 47b-815
– Chugaev reaction 47b-816, 817
– Chugaev synthesis 47b-816
Claisen reaction
– Claisen approach 47a-533
– Claisen product 44-376
– Claisen reaction 44-375f.
Claisen rearrangement
– [3,3] enol ether Claisen rearrangement 43-322, 328
– Claisen rearrangement 43-14, 25, 268f., 322, 328, 471–475, 44-5, 295, 375f., 45b-1212, 1213, 1235, 46-578–580, 47a-173–175, 186, 193, 194, 199, 529, 741, 1026
– Claisen rearrangement, thermal 44-5, 295
– Hetero-Claisen rearrangement 43-474, 46-619, 622
– Metallo-Claisen rearrangement 47b-746
– Propargyl Claisen rearrangement 43-525
– Retro-Claisen product 45a-355
– Thio-Claisen rearrangement 43-475
Clemmensen reduction
– Clemmensen method 48-139
– Clemmensen reaction 48-136
– Clemmensen reduction 45a-187, 45b-1166, 1298, 1314, 1315, 1322, 1338, 48-4, 97–99, 101, 103, 114, 126
– Clemmensen reduction, Martin modification 48-99, 100
Coarctate rearrangement
– Coarctate rearrangement 43-26f., 532
Conia reaction
– Conia-ene reaction 48-679
Cope elimination
– Cope elimination 47b-821, 822
Cope rearrangement
– Cope rearrangement 43-471–474, 44-414, 428, 45a-356, 358, 373, 46-578, 47a-3, 763–767, 48-636, 637
– Oxa-Cope product 45a-355
– Oxy-Cope [3,3]-sigmatropic rearrangement 43-317
– Oxy-Cope rearrangement 43-317, 45b-937, 943
– Siloxy-Cope rearrangement 48-671
– Cope rearrangement, [3,3]sigmatropic 43-471f.
– Cope rearrangement, propargylic 43-471f.
Corey reaction
– Corey iodolactonization 47b-834
– Corey's conditions 44-189
Corey–Fuchs reaction
– Corey–Fuchs alkenation 43-13, 345, 46-290
– Corey–Fuchs alkynylation 43-18, 381f.
– Corey–Fuchs conditions 43-77
– Corey–Fuchs dibromoalkenation 43-249
– Corey–Fuchs method 43-456
– Corey–Fuchs methodology 43-444
– Corey–Fuchs modification 43-18, 381
– Corey–Fuchs procedure 43-377, 444
– Corey–Fuchs process 43-24
– Corey–Fuchs reaction 43-254, 381, 442, 46-244, 332, 47b-910, 911
– Corey–Fuchs reaction, modified 43-24, 444
– Corey–Fuchs synthesis 43-443, 444
– Corey–Fuchs technique 43-100
Corey–Fuchs–Wittig reaction
– Corey–Fuchs-type Wittig alkenation 43-100
– Corey–Fuchs–Wittig alkenation 43-77
Corey–Kim reagent
– Corey–Kim reagent 46-599
Corey–Schlesinger–Mills reaction
– Corey–Schlesinger–Mills modified Peterson alkenation 46-338, 47b-910
Corey–Winter reaction
– Corey–Winter alkenation 47b-851
– Corey–Winter fragmentation 43-14f., 315, 323, 327
– Corey–Winter reaction 43-247, 45a-408
– Corey–Winter synthesis 45a-408
Crabtree's catalyst
– Crabtree's catalyst 48-343–345, 347, 348, 364
– Crabtree-type catalyst 48-342
Cram modification
– Wolff–Kishner reduction, Cram modification 48-120
Cram's rule
– Cram hemicarcerand 44-420
– Cram's rule 47a-88, 92
– Cram's rule controlled 47a-98
Cram–Henbest modification
– Wolff–Kishner reduction, Cram–Henbest modification 48-112, 119
Criss-cross cycloaddition
– Criss-cross cycloaddition 48-572
Cross coupling
– Alkenyl–alkenyl coupling 46-13
– Coupling 47b-1102
– Cross benzannulation 43-138, 429f.
– Cross carbonylation 45a-41
– Cross coupling 43-17, 41, 47, 52, 60, 68f., 89, 91, 225, 229, 230, 232, 234–236, 311, 345f., 349, 351–359, 361, 365–374, 396–398, 401–404, 420, 44-6, 132, 151, 164, 238, 308–313, 45a-6, 81, 174, 175, 177, 227, 238, 244, 384, 387–389, 403, 45b-547, 549, 552, 553, 558, 567, 569, 571, 573, 581, 589, 601, 603, 627, 636, 643, 644, 649, 782–785, 815, 907, 1268, 1269, 1340, 1344, 1345, 1351, 1361, 46-11, 12, 79, 243, 244, 256–265, 267, 269, 271–275, 283, 285–287, 290, 293, 294, 298, 300–306, 308, 309, 324, 325, 335–342, 415, 47a-2, 6, 191, 232, 274, 276–278, 285, 439, 440, 442–445, 447, 451, 452, 454, 455, 457–460, 464, 465, 467–473, 526, 585, 909, 910, 913–966, 971, 972, 982, 984, 1003, 1004, 1008, 1010–1013, 1104, 1106, 1108, 1138–1141, 1143, 1144, 1146, 1147, 48-3, 29, 33, 40, 42, 51, 52, 59, 63, 77, 87, 416
– Cross coupling, copper catalyzed 44-314
– Cross coupling, palladium catalyzed 44-101, 130, 131f., 167, 231, 312
– Cross coupling, regioselective 44-131
– Cross dimerization 47a-285
– Homocoupling 45a-385, 388, 424, 45b-1362, 47b-1145, 48-3, 77, 78, 80, 81, 87, 89
Curtius elimination
– Curtius elimination 43-24
Curtius rearrangement
– Curtius rearrangement 45a-354
D
Danishefsky's diene
– Danishefsky's diene 45b-845, 908, 47b-579, 588, 593, 594, 604, 608–610, 642
Darvon alcohol
– Darvon alcohol 44-83, 386
Dess–Martin oxidation
– Dess–Martin oxidation 44-440
– Dess–Martin periodinane 43-250, 44-291, 320, 45b-1370, 47a-33, 36
Dewar benzene
– Dewar benzene 43-22, 338, 430f., 45a-52, 58, 45b-771, 1286–1290, 1306, 1337, 48-633, 634
– Dewar phosphinine 45a-52
– Dewar pyridine 45a-52, 58
Dieckmann cyclization
– Dieckmann reaction 45b-823, 824
Diels–Alder reaction
– Cascade Diels–Alder reaction 47b-562
– Dehydro-Diels–Alder reaction 44-402, 45b-968
– Diels–Alder addition 45b-1275
– Diels–Alder addition, intramolecular 43-16
– Diels–Alder adduct 43-317, 44-354, 45a-66, 67, 398, 399, 45b-717, 761, 779, 790, 798, 808, 809, 843, 868, 869, 1029, 1037, 1069, 1096, 1178, 1298, 1338, 46-357, 401, 418–420, 425, 426, 436, 437, 439, 471, 662, 47b-608, 612, 635, 640, 641, 659, 1130, 48-374, 629
– Diels–Alder approach 43-190, 45b-934, 942, 47b-588, 656, 657, 658, 682
– Diels–Alder cycloaddition 43-146, 162, 314, 44-353–355, 357, 418, 45a-391, 402, 45b-673, 725, 907, 908, 910, 933–935, 942, 1029, 1031, 1119, 46-97, 224, 47b-561, 564, 566, 570, 572, 585, 628, 642, 651, 656, 660–662, 679, 682, 688, 702, 707, 708, 713, 715, 722
– Diels–Alder cycloaddition, face selective 47b-678
– Diels–Alder cycloaddition, thermal 47b-626
– Diels–Alder cycloadduct 44-353, 46-132
– Diels–Alder diene 44-354, 355f.
– Diels–Alder diene synthesis 47b-564
– Diels–Alder dienophile 44-354
– Diels–Alder dimer 46-402
– Diels–Alder dimerization 47b-707
– Diels–Alder manner 45a-359
– Diels–Alder polycondensation 45b-668, 669
– Diels–Alder procedure 47b-591
– Diels–Alder product 45b-986
– Diels–Alder reaction 43-137f., 153, 175, 187–190, 44-353, 355, 356f., 401, 45a-62, 67, 143, 147, 288, 320, 350, 420, 522, 45b-746, 750, 752, 753, 759–763, 771, 772, 790–792, 794–796, 798, 799, 809, 822, 823, 840, 842–845, 868–870, 907, 910, 934, 1029, 1037, 1049, 1070, 1105, 1278, 1279, 1306, 46-66, 131, 132, 150, 173, 183, 355, 384, 418, 420, 429, 434, 448, 652, 662, 47a-2, 7, 26, 414, 561–723, 737, 48-553, 678
– Diels–Alder reaction, allenic 44-6
– Diels–Alder reaction, asymmetric 47b-639, 671, 683, 686
– Diels–Alder reaction, diastereoselective 47b-710
– Diels–Alder reaction, enantioselective 47b-632, 710
– Diels–Alder reaction, exo-selective 47b-723
– Diels–Alder reaction, intermolecular 47b-561
– Diels–Alder reaction, intramolecular 43-314, 323, 44-245, 46-402, 410, 436, 47b-562, 607, 644–647
– Diels–Alder reaction, inverse-electron-demand 46-404, 47b-566, 567, 577, 578
– Diels–Alder reaction, multiple 47b-561
– Diels–Alder reaction, neutral-electron-demand 47b-566
– Diels–Alder reaction, normal-electron-demand 47b-567, 575–579
– Diels–Alder reaction, thermal 47b-579, 597, 612, 718
– Diels–Alder reaction, thermal, asymmetric 47b-593
– Diels–Alder reactivity 45b-1093
– Diels–Alder substrate 46-563
– Diels–Alder trapping 46-405, 420
– Diels–Alder-type reaction 45a-346
– Domino Diels–Alder reaction 47b-562
– Hetero-Diels–Alder cycloaddition 47b-561
– Hetero-Diels–Alder reaction 45a-305, 371, 46-648, 47b-561, 562
– Homo-Diels–Alder cycloaddition 48-484, 486, 487
– Homo-Diels–Alder cycloadduct 48-486
– Homo-Diels–Alder reaction 47b-571
– Imino-Diels–Alder reaction 45a-321, 46-619
– Pseudo Diels–Alder reversal 48-623
– Retro-Diels–Alder product 45b-1413
– Retro-Diels–Alder reaction 43-317, 472, 494, 44-6, 25f., 50, 45a-438, 522, 536, 45b-1049, 1096, 46-402, 425, 435–437, 590, 603, 47b-567, 570, 604, 623, 750
– Retro-oxy-Diels–Alder reaction 43-318
– Tandem Diels–Alder–carbon dioxide extrusion–Diels–Alder reaction 46-405
– Tandem Diels–Alder reaction 47b-562
– Transmissive Diels–Alder reaction 47b-563
Doering protocol
– Doering protocol 48-528, 532
– Doering's conditions 48-528, 529, 531
Doering–LaFlamme synthesis
– Doering–LaFlamme allene synthesis 44-40
Doering–Moore–Skattebøl reaction
– Doering–Moore–Skattebøl protocol 44-22, 25
– Doering–Moore–Skattebøl reaction 44-218, 395–397, 400, 407, 408, 410, 412, 413, 415, 418, 427, 431, 433, 435, 439
– Doering–Moore–Skattebøl synthesis (DMS) 44-4
Dötz reaction
– Dötz reaction 43-345, 45b-1404, 46-131
Duboudin reaction
– Duboudin anti-carbomagnesiation 47b-978
Dzhemilev reaction
– Dzhemilev ethylmagnesiation 47b-975, 978, 48-415
– Dzhemilev reaction 48-410
E
Eastwood reaction
– Eastwood deoxygenation 47b-851
– Eastwood method 47b-851
Eglinton coupling
– Eglinton conditions 43-42, 49, 121, 122f., 415
– Eglinton conditions, modified 43-122
– Eglinton coupling 43-16, 42f., 84, 124, 126, 408–412, 414, 417
– Eglinton coupling, modified 43-126
– Eglinton cross coupling 43-44
– Eglinton cyclooligomerization 43-122
– Eglinton homocoupling 43-89
– Eglinton method 43-123
– Eglinton modification 43-51
– Eglinton procedure 43-43
– Eglinton protocol 43-84
– Eglinton reaction 43-325, 408, 412, 414, 418
– Eglinton route 43-20
– Eglinton variant 43-4
– Eglinton-type coupling 43-405, 416
– Eglinton-type homocoupling 43-42
– In situ deprotection–Eglinton-type coupling 43-416f.
Elbs reaction
– Elbs reaction 45b-794, 836
Ene reaction
– Alder-ene reaction 47b-737, 745, 749, 891, 1143
– Alder-ene-like product 47b-749
– Claisen ene sequence 47b-741
– Cross-ene reaction 47b-740
– Ene reaction 43-476f., 44-390f., 47a-3, 737–739, 1129
– Ene reaction, intermolecular 47b-739, 740, 749
– Ene reaction, intramolecular 47b-738, 740–742
– Ene reaction type I, intramolecular 47b-740
– Ene-type reaction 48-672
– Metalla-ene reaction 44-391
– Metallo-ene cyclization 47b-745
– Metallo-ene product 47b-747
– Metallo-ene reaction 47a-7, 743, 744, 747, 748, 977
– Metallo-ene reaction, intramolecular 47b-745, 747
– Metallo-ene reaction, type I 47b-745
– Metallo-ene reaction, type II 47b-745
– Pallada-ene product 47b-747
– Retro-ene reaction 43-476–478, 47b-750, 751
Eschenmoser fragmentation
– Eschenmoser fragmentation 43-656f.
Eschenmoser rearrangement
– Eschenmoser's procedure 45b-1100
– Eschenmoser-type rearrangement 46-557
Eschenmoser–Tanabe reaction
– Eschenmoser–Tanabe fragmentation 43-27, 537
– Eschenmoser–Tanabe reaction 43-537–539
F
Favorskii rearrangement
– Favorskii cleavage 43-404
– Favorskii isomerization 43-26
– Favorskii rearrangement 48-687, 688
– Favorskii-type ring contraction 45a-348
Felkin–Anh selectivity
– Felkin–Anh product 47a-99
– Felkin–Anh selectivity 47a-98
– Felkin–Anh-controlled reaction 44-305
Finkelstein reaction
– Finkelstein-type reaction 44-317
Fischer carbene
– Fischer carbene 45a-85, 282, 45b-1284, 46-100, 128, 131, 47b-651–654, 48-684
– Fischer chromium carbene complex 45b-1404
– Fischer-type carbene 47a-365
– Fischer-type chromium carbene complex 45b-1284
Fréchet dendron
– Fréchet dendron 43-90, 91
– Fréchet's polyether dendrimer 43-90
Friedel–Crafts reaction
– Friedel–Crafts acetylation 45b-787, 870
– Friedel–Crafts acylation 43-77, 100, 102, 44-259–261, 45a-289, 291, 45b-764, 816, 836, 837, 898, 908, 922, 1201, 1229, 1245, 1321, 48-98
– Friedel–Crafts alkylation 43-378, 44-260f., 45a-159–163, 165, 166, 168, 170, 172, 45b-627, 628, 632, 634, 731, 764, 765, 781, 809, 810, 826, 1008, 47b-636, 48-400
– Friedel–Crafts annulation 45a-307
– Friedel–Crafts approach 47a-533
– Friedel–Crafts chemistry 45a-1, 45b-627
– Friedel–Crafts conditions 45a-163
– Friedel–Crafts coupling 45b-698
– Friedel–Crafts cyclization 45a-289, 309, 310, 45b-922
– Friedel–Crafts cycloacylation 45b-921
– Friedel–Crafts cycloacylation, intramolecular 45b-889, 890
– Friedel–Crafts cycloalkylation 45b-898, 922, 923
– Friedel–Crafts cycloalkylation, intramolecular 45b-889
– Friedel–Crafts formylation 45b-1315
– Friedel–Crafts reaction 45a-21, 307, 308, 45b-627, 746, 765, 780, 810, 870, 1321, 1338, 47a-389
– Friedel–Crafts reaction, asymmetric 45b-635
– Friedel–Crafts reagent 45b-921
– Friedel–Crafts substitution 45a-172
– Friedel–Crafts-type alkylation 45a-166, 172, 183, 195
– Friedel–Crafts-type allylation 47a-534
– Friedel–Crafts-type reaction 45a-20, 47a-535, 536, 48-400
– Friedel–Crafts catalyst 48-729
Fries rearrangement
– Fries rearrangement 45b-1236
Fritsch–Buttenberg–Wiechell rearrangement
– Electrochemical Fritsch–Buttenberg–Wiechell
rearrangement 43-26, 487
– Fritsch–Buttenberg–Wiechell alkynyl migration 43-101
– Fritsch–Buttenberg–Wiechell conditions 43-102, 143
– Fritsch–Buttenberg–Wiechell precursor 43-44
– Fritsch–Buttenberg–Wiechell process 43-7
– Fritsch–Buttenberg–Wiechell reaction 43-38, 142, 483, 485, 487, 488, 491
– Fritsch–Buttenberg–Wiechell rearrangement 43-3f., 6, 10, 18, 24f., 44, 77f., 87, 99, 100–103, 143, 251, 254, 271, 345, 376f., 445f., 483–485, 488, 658
– Fritsch–Buttenberg–Wiechell strategy 43-446
– Photo-Fritsch–Buttenberg–Wiechell rearrangement 43-25, 486f.
Furrow–Myers modification
– Wolff–Kishner reduction, Furrow–Myers modification 48-112, 123
G
Garner's aldehyde
– Garner's aldehyde 44-109
Garpar–Roth protocol
– Garpar–Roth conditions 48-513
– Garpar–Roth protocol 48-512–514
Gaudemar–Normant coupling
– Gaudemar–Normant coupling 47b-746
Gibbs energy
– Gibbs energy 45b-926, 927
Gilch method
– Gilch method 45b-683, 684, 687
Gilman reagent
– Cyano-Gilman reagent 44-101, 246
– Gilman cuprate 44-246
– Gilman reagent 47a-496, 498, 506, 48-32
– Gilman-type reagent 44-97
Glaser coupling
– Glaser-type conditions 43-41
– Glaser conditions 43-40f., 51
– Glaser coupling 43-1, 4f., 7, 16, 39f., 83, 360
– Glaser cross coupling 43-84
– Glaser method 43-4
– Glaser procedure 43-39
– Glaser reaction 43-49, 325
– Glaser route 43-20
– Glaser's reaction 43-39
– Glaser-like coupling 43-490
– Glaser-type coupling 43-405
– Glaser-type dimerization 43-57
– Glaser-type oxidative coupling 43-363, 365
– Glaser conditions 43-120f.
Glaser–Eglinton coupling
– Glaser–Eglinton conditions 43-120
Goré reagent
– Goré cuprate reagent 44-101
Gorham process
– Gorham process 45b-712
Grevel's reagent
– Grevel's reagent 46-640
Grignard coupling
– Grignard coupling 45b-659
Grob fragmentation
– Grob fragmentation 46-473–475
– Grob-type fragmentation 47b-778
Grubbs catalyst
– Grubbs carbene 46-98–102, 112, 119, 121, 123–125, 127, 132, 135, 140, 141
– Grubbs carbene complex 44-341, 46-5, 369
– Grubbs catalyst 43-530, 45a-203, 315, 45b-895, 915, 916, 46-6, 97–99, 102, 106, 107, 112, 115, 127, 131, 133, 135, 139, 141, 142, 47a-327, 334, 335, 339–371, 374–403, 407, 408, 411–414, 416, 417, 419, 421–430, 1068, 48-653
– Grubbs catalyst, first generation 44-438, 45b-1318, 46-121, 135, 141, 47a-327, 328, 340, 419, 426
– Grubbs catalyst, second generation 43-13, 243, 45b-690, 1317, 46-119–123, 125, 131, 134, 135, 419, 47a-327, 328, 387, 427
– Grubbs catalyst, third generation 47a-329
– Grubbs complex 46-98–101, 104, 112, 116, 118, 125, 133, 135, 140
– Grubbs indenylidene initiator 47a-330
– Grubbs model 46-127, 135
– Grubbs precatalyst, first generation 47a-387
– Grubbs precatalyst, second generation 47a-387
– Grubbs-type catalyst 47a-328, 330, 387, 417
Grubbs–Hoveyda catalyst
– Grubbs–Hoveyda carbene catalyst 45b-689
Gustavson reaction
– Gustavson reaction 48-489
H
Hafner method
– Hafner method 45b-1084, 1085
– Hafner's one-pot procedure 45b-1092
– Hafner's procedure 45b-1093, 1094
Hagihara–Sonogashira coupling
– Hagihara–Sonogashira coupling 43-399f.
– Hagihara–Sonogashira reaction 43-396, 399
– Hagihara–Sonogashira-type cross coupling 43-401
Hajos–Wiechert dione
– Hajos–Wiechert dione 48-110
Haller–Bauer reaction
– Haller–Bauer reaction 48-445
Hay coupling
– Hay conditions 43-9, 44, 64, 86–90, 127–129
– Hay coupling 43-5, 7f., 16, 44f., 86–90, 127, 405, 406f.
– Hay cross coupling 43-88
– Hay homocoupling 43-44, 87–89
– Hay modification 43-51
– Hay oligomerization protocol 43-46
– Hay polymerization 43-46
– Hay protocol 43-7
– Hay reaction 43-325, 333, 406f.
– Hay route 43-20
– Hay synthesis 43-49
– Hay's conditions 43-44, 47
– Hay coupling, intramolecular 43-129
Heck reaction
– Heck alkenylation 46-243
– Heck arylation 48-670
– Heck conditions 43-65, 45a-235
– Heck coupling 45a-228, 230, 45b-688, 689, 1357, 1360
– Heck cyclization 45a-294
– Heck protocol 46-302
– Heck reaction 43-325, 359, 45a-228, 229, 292, 295, 45b-620, 688, 1087, 1360, 46-208, 244, 251, 308–314, 316, 380, 382, 642, 47a-2, 439, 440, 441, 910, 956
– Heck reaction, decarbonylative 45a-234
– Heck reaction, desulfonylative 45a-236
– Heck reaction, intramolecular 47a-440
– Heck selectivity 45b-1357
– Heck synthesis 45a-227, 229
– Heck synthesis, desulfonylative 45a-237
– Heck-type arylation 45b-1033
– Heck-type coupling 47a-466
– Heck-type reaction 44-312, 46-316, 317, 326
Heck–Sonogashira coupling
– Heck–Sonogashira alkynylation 46-243, 302, 47b-941
– Heck–Sonogashira conditions 47b-941
– Heck–Sonogashira coupling 46-301, 302
– Heck–Sonogashira methodology 47b-941
Henbest modification
– Wolff–Kishner reduction, Henbest modification 48-120
Hermann's catalyst
– Herrmann's catalyst 45b-608, 609
– Herrmann's palladacycle 45b-987
Hieber reaction
– Hieber-type reaction 46-661
Hiyama coupling
– Hiyama coupling 45a-182, 45b-591–593, 595–597, 627, 642, 1351, 47b-910
– Hiyama cross coupling 45a-182, 45b-591, 593, 594, 596–599, 641, 649
– Hiyama reaction 45a-227, 239, 45b-547
– Hiyama synthesis 45a-240
– Hiyama-type cross coupling 45a-182
Hofmann elimination
– Hofmann base 45a-520
– Hofmann decomposition 45a-487
– Hofmann degradation 45b-700
– Hofmann elimination 45a-383, 398, 471, 487, 515, 516, 520, 45b-1307, 1335, 47b-792, 794
– Hofmann 1,6-elimination 45b-701
– Hofmann-analogous 1,6-elimination 45b-701
– Hofmann-type elimination 45b-1326
Hofmann rule
– Hofmann product 47b-781, 784, 796
– Hofmann rule 47b-781, 824
– Hofmann/Zaitsev ratio 47b-795, 796
– Hofmann-type product 47b-812
Hopf cyclization
– Hopf cyclization 44-401, 406
Horiuti–Polanyi mechanism
– Horiuti–Polanyi mechanism 48-275, 282, 323
– Horiuti–Polanyi proposal 48-275
Horner reaction
– Horner reaction 45b-687, 688, 47a-47
Horner–Emmons reaction
– Horner–Emmons alkenation 44-330, 47a-61, 64
– Horner–Emmons conditions 45a-85
– Horner–Emmons protocol 47a-61
– Horner–Emmons protocol, Still–Gennaro modification 47a-61
– Horner–Emmons reaction 44-48, 45b-1368, 46-138, 47a-58, 68
– Horner–Emmons synthesis 47a-66
– Horner–Emmons-type reaction 44-48
– Wittig homologation 45b-1352
Horner–Wadsworth–Emmons reaction
– Double Horner–Wadsworth–Emmons reaction 44-204
– Horner–Wadsworth–Emmons alkenation 43-380, 45a-214, 46-341, 47b-910
– Horner–Wadsworth–Emmons modification 45a-209, 210, 45b-1369, 1371
– Horner–Wadsworth–Emmons product 45b-1371
– Horner–Wadsworth–Emmons reaction 44-204, 206, 207, 45a-214, 45b-1109, 1369, 1371, 46-1, 2, 23, 39, 40–43, 45, 46, 63, 278, 332, 47a-49, 910
– Horner–Wadsworth–Emmons reagent 44-209f., 45b-1371, 1372, 46-339
– Horner–Wadsworth–Emmons reagent, chiral 44-4
– Horner–Wadsworth–Emmons-type route 43-380
– Wadsworth–Horner–Emmons reagent 43-250
Horner–Wittig reaction
– Horner–Wittig alkenation 45a-213
– Horner–Wittig methodology 45a-212
– Horner–Wittig modification 45a-209
– Horner–Wittig reaction 45a-210, 212, 45b-1369, 46-1, 23, 37, 38
Horner–Wittig–Emmons reaction
– Horner–Wittig–Emmons alkenation 46-647
Hoveyda catalyst
– Hoveyda catalyst 47a-328, 329, 334, 335, 337, 357, 360, 362, 374, 381, 421
– Hoveyda complex 47a-328
– Hoveyda-type catalyst 47a-330, 365, 380, 387
– Hoveyda-type initiator 47a-330
Hoveyda–Blechert catalyst
– Hoveyda–Blechert catalyst 46-99–102, 112, 113, 141
– Hoveyda–Blechert complex 46-138
– Hoveyda–Blechert-type catalyst 46-127
– Hoveyda–Blechert-type initiator 46-127
Hoveyda–Grubbs catalyst
– Grubbs–Hoveyda alkylidene complex 47a-376
– Hoveyda–Grubbs carbene complex 47a-398
– Hoveyda–Grubbs catalyst 46-99
– Hoveyda–Grubbs complex 46-112–114, 47a-328, 348
– Hoveyda–Grubbs precatalyst 47a-387
Huang–Minlon modification
– Huang–Minlon conditions 48-133
– Huang–Minlon modification 48-97
– Huang–Minlon reduction 48-129
– Wolff–Kishner reduction, Huang–Minlon conditions 48-114
– Wolff–Kishner reduction, Huang–Minlon modification 48-112, 114, 117, 120, 140
– Wolff–Kishner reduction, Huang–Minlon procedure 48-120
– Wolff–Kishner reduction, Huang–Minlon reduction 48-115
Hückel rule
– Hückel ring system 45a-11
Hunsdiecker–Borodin degradation
– Hunsdiecker–Borodin-type degradation 48-592
I
Ireland rearrangement
– Ireland-type rearrangement 46-557
Ireland–Claisen rearrangement
– Ireland–Claisen rearrangement 46-557
J
Johnson rearrangement
– Johnson-type rearrangement 46-557
Joule–Thompson effect
– Joule–Thompson effect 48-698
Julia reaction
– Julia alkenation 45a-209, 216, 45b-1365–1367, 1389, 47a-1, 2, 105, 113, 152, 155
– Julia alkenation, modified 45a-218, 219
– Julia alkenation, second generation 47a-144–147, 149, 151–153, 155
– Julia method 45b-1390
– Julia reaction 45a-209, 216, 45b-1350, 46-1, 2, 54, 55, 57, 47a-105
– Julia reaction, modified 45a-218
– Julia reaction, one-pot 46-55, 56, 58
– Julia reaction, second generation 47a-143
– Julia reaction, two-step 46-56
– Julia reductive elimination 45a-216
– Retro-Julia disconnection 47a-106
– S. Julia alkenation 47a-143
Juliá–Colonna reaction
– Juliá–Colonna reaction 46-628
Julia–Kocienski reaction
– Julia–Kocienski alkenation 45a-218, 45b-1368, 1369, 1391, 47a-1, 2, 105, 143, 144, 152
– Julia–Kocienski reaction 45b-1368, 1392
Julia–Lythgoe reaction
– Julia–Lythgoe alkenation 43-249, 45a-216, 47a-105, 115, 119, 123, 125–127, 135, 138, 142, 143
– Julia–Lythgoe elimination 47a-130
– Julia–Lythgoe protocol 45b-1367
– Julia–Lythgoe reaction 45a-216, 47a-144
– Julia–Lythgoe sequence 47a-109
K
Kambe's protocol
– Kambe's protocol 48-52
Katsuki–Sharpless epoxidation
– Katsuki–Sharpless asymmetric epoxidation 44-92
Keck reaction
– Keck variation of the Julia reaction 46-59, 60
Keggin catalyst
– Keggin-type polyoxometalate catalyst 45a-193
Kishner–Leonard elimination
– Kishner–Leonard elimination 48-113
Knochel's catalyst
– Knochel's catalyst 48-52
– Knochel's protocol 48-52
– Knochel-type Grignard reagent 45b-600
Knoevenagel condensation
– Knoevenagel alkenation 43-13
– Knoevenagel approach 46-160, 162
– Knoevenagel condensation 45a-129, 45b-692, 693, 838, 1029, 1082, 1398, 1399, 46-162–165
– Knoevenagel conditions 46-161
– Knoevenagel reaction 43-249
– Knoevenagel reaction, vinylogous 46-165
– Knoevenagel strategy 46-153
– Knoevenagel strategy, vinylogous 46-164
– Knoevenagel-type condensation 43-251, 45a-430
– Knoevenagel-type preparation 46-163
– Domino Knoevenagel reaction 47b-561
Kochi's catalyst
– Kochi's catalyst 48-38, 40
Kolbe electrolysis
– Kolbe electrolysis 48-3, 85
– Kolbe reaction 48-29, 89
Kosugi–Migita–Stille coupling
– Kosugi–Migita–Stille coupling 45a-227, 47a-440, 447
– Kosugi–Migita–Stille reaction 45a-240, 47a-447
Krätschmer–Huffman reaction
– Krätschmer–Huffman conditions 43-108
Kumada coupling
– Kumada coupling 43-230, 45a-178, 403, 45b-600, 627, 636–638, 643
– Kumada cross coupling 45a-178, 179, 45b-636, 643
– Kumada-type cross coupling 43-230, 45a-178
Kumada–Corriu coupling
– Kumada–Corriu coupling 43-230, 45b-599–603, 605
– Kumada–Corriu cross coupling 43-13, 230, 45b-599, 601, 603–605
– Kumada–Corriu procedure 45b-547
– Kumada–Corriu reaction 43-566
– Kumada–Corriu-type coupling 43-355
Kumada–Tamao coupling
– Kumada–Tamao coupling 45b-1258
Kumada–Tamao–Corriu coupling
– Corriu–Kumada–Tamao coupling 47a-450, 463, 467
– Corriu–Kumada–Tamao reaction 47a-440, 450, 463
– Kumada–Tamao–Corriu coupling 47b-910, 48-38, 40, 42, 44, 46, 47
– Kumada–Tamao–Corriu cross coupling 48-42
– Kumada–Tamao–Corriu reaction 48-3, 29, 37, 38, 40
Kuwabata–Furukawa method
– Furukawa protocol 48-521
– Kuwabata–Furukawa method 48-519–521
L
Lalezari reaction
– Lalezari reaction 43-290
Lalezari–Meier fragmentation
– Lalezari–Meier fragmentation 43-32
Landor reagent
– Landor reagent 44-101
Lawesson's reagent
– Lawesson's reagent 45a-362, 45b-1005, 48-169
Liche reduction
– Liche conditions (reduction) 44-325
Linchpin reagent
– Linchpin reagent 45b-1357
Lindlar catalyst
– Lindlar catalyst 45a-410, 46-523–527, 529, 531, 47b-897, 898
– Lindlar catalyst, poisoned 46-527, 528
– Lindlar's catalytic hydrogenation 46-326
– Lindlar-type catalyst 47b-897
Lipshutz reagent
– Lipshutz cuprate 45b-1342
Lombardo reaction
– Lombardo reagent 46-75, 76, 47a-208, 209, 211
– Lombardo's modification of theTakai–Ohshima procedure 46-75
Lowe–Brewster rule
– Lowe–Brewster rule 44-151
M
Mander's reagent
– Mander's reagent 44-363
Mannich reaction
– Mannich base 47b-778
– Mannich reaction 44-375, 46-647, 48-671
Markovnikov orientation
– Anti-Markovnikov addition 44-123
– Markovnikov addition 44-123
Martin modification
– Martin modification, Clemmensen reduction 48-99, 102
Martin reagent
– Martin sulfurane 46-451, 452
Maryanoff reagent
– Maryanoff ylide 47a-49
Matsuda–Heck reaction
– Matsuda–Heck reaction 45a-232, 233
– Matsuda–Heck synthesis 45a-233
Matteson's reagent
– Matteson's reagent 46-52
McMurry coupling
– McMurry coupling 43-249, 434, 45a-220, 409, 410, 419, 45b-692, 996, 1318, 1319, 47a-1, 2, 247, 248, 250–258, 260, 262, 264, 265, 268, 273, 275, 277, 280, 282, 284, 287, 292, 297, 299, 301, 308, 310, 312, 318, 320, 836
– McMurry coupling, intermolecular 47a-318
– McMurry coupling, intramolecular 47a-288, 290, 291, 293, 296, 298, 301, 302, 306, 310, 311, 313–315
– McMurry coupling, twofold 47a-302, 304
– McMurry cross coupling 47a-276, 278, 279
– McMurry reaction 45a-220, 45b-692, 894, 917, 1318–1320
– McMurry self-coupling 47a-262, 270
– McMurry synthesis 45a-221
– McMurry-type coupling 43-16
– McMurry-type cross coupling 47a-278
– McMurry-type self-coupling 47a-252
Meerwein–Ponndorf–Verley reduction
– Meerwein–Ponndorf–Verley reduction 45b-806, 829, 845
Meldrum's acid
– Meldrum's acid 45a-290
Metathesis
– Alkene metathesis 43-243, 45b-1317, 46-4, 47a-1, 2, 327–430
– Alkene–diene metathesis 46-6
– Alkyne cross metathesis 43-386
– Alkyne metathesis 43-26, 243f., 385, 420–422, 516–519
– Co-metathesis 46-131
– Cross ene–yne metathesis 47a-331, 391–402
– Cross enyne metathesis 46-97, 99
– Cross metathesis 45a-226, 227, 46-98, 100, 104, 114, 118, 121–130, 132, 136–141, 47a-332–364, 419, 439, 910, 1068
– Diene–ene metathesis 46-97
– Diene metathesis 45b-690
– Diene metathesis polymerization 47a-331
– Diene metathesis, acyclic 47a-415
– Diyne metathesis, acyclic 43-387
– Ene–yne metathesis 46-5, 97, 47a-391–414
– Ene–yne ring-closing metathesis 47a-331
– Enyne cross-metathesis 46-5
– Enyne metathesis 43-14, 46-5, 97, 98, 102–105, 107, 110, 113, 115–117, 121, 125–130, 132
– Intramolecular metathesis 47a-31
– Metathesis 43-18, 345, 385, 393, 44-339, 341f., 438, 45a-273, 46-97–102, 107–110, 114, 47a-327–430
– Metathesis, intermolecular 45b-1318
– Metathesis–hydrogenation sequence 48-685
– Metathesis polymerization 45b-689
– Metathesis reaction 43-243
– Ring-closing alkene metathesis 45b-1317
– Ring-closing alkyne metathesis 43-386f., 644–647
– Ring-closing ene–yne metathesis 47a-402–414
– Ring-closing metathesis 43-31, 644, 45b-770, 895, 915, 916, 46-5, 98, 102–105, 107, 108, 113, 115–120, 142, 47a-331, 364–391, 48-653, 654
– Ring-closing metathesis, asymmetric 47a-385
– Ring-forming metathesis 46-107
– Ring-opening metathesis 45b-82, 681, 690, 691, 46-143, 47a-331, 419
– Ring-opening metathesis polymerization 47a-428
– Ring-opening/cross metathesis 47a-419–425
– Ring-opening/ring-closing metathesis 47a-425
– Ring-rearrangement metathesis 46-141–143
– Tanden enyne metathesis 46-114
Meyers reaction
– Meyers protocol, Ramberg–Bäcklund reaction 47b-848
Michael addition
– Anti-Michael addition 44-246
– Domino Michael–aldol reaction 48-672
– Michael acceptor 44-3, 371, 373, 45a-448
– Michael addition 44-261, 45a-431, 45b-1080, 1102, 1104, 1107, 46-149, 370, 377, 47a-69
– Michael 1,4-addition 44-209
– Michael addition, intramolecular 44-379, 48-671
– Michael addition, sequential 44-371
– Michael addition–intermolecular ring closure
(MIRC) 48-495
– Michael adduct 44-373, 46-377
– Michael attack, intramolecular 44-383
– Michael-type addition 47a-116, 48-666
Michael addition/Horner–Wadsworth–Emmons
reaction
– Tandem Michael/Horner–Wadsworth–Emmons reaction 44-209
Michael addition/aldol/Horner–Wadsworth–Emmons reaction
– Tandem Michael/aldol/Horner–Wadsworth–Emmons reaction 44-206
Michellamine
– Michellamine 45b-568
Migita–Stille coupling
– Migita–Stille coupling 47a-447
MIRC
– Michael addition–intermolecular ring closure 48-495
Mirozoki–Heck reaction
– Mirozoki–Heck coupling 45a-228, 229
– Mirozoki–Heck reaction 45a-227, 230, 231
– Mirozoki–Heck synthesis 45a-228
Mitsunobu reaction
– Mitsunobu conditions 48-173
– Mitsunobu displacement 48-170
– Mitsunobu inversion 44-87, 48-171
– Mitsunobu method 44-90
– Mitsunobu reaction 44-319, 46-124
– Mitsunobu-type amination 44-97
Mizoroki–Heck reaction
– Mizoroki–Heck reaction 45b-911, 47a-1, 440
– Mizoroki–Heck-type reaction 47a-466
Mçbius aromaticity
– Mçbius aromaticity 45a-413
Mori reaction
– Mori conditions 46-102, 103, 130
– Mori's conditions 47a-405
Morita reaction
– Morita reaction 45b-1066
Mosher ester
– Mosher ester 44-86
Mukaiyama reaction
– Mukaiyama aldol reaction 44-377, 46-651, 660
– Mukaiyama variation 45b-1388
Murai coupling
– Murai coupling 45b-636
N
Naarmann method
– Naarmann method 45b-1422
Nagata–Itazaki modification
– Nagata–Itazaki method 48-121
– Wolff–Kishner reduction, Nagata–Itazaki modification 48-112, 121
Nazarov reaction
– Nazarov cyclization 44-363, 364f., 45a-291, 292, 45b-1082, 1083
– Nazarov reaction 44-362–364, 45b-1082
– Nazarov-type cyclization 45b-1084
– Domino-Nazarov/Friedel–Crafts reaction 44-179
Nef reaction
– Nef-type reaction 45b-1291
Negishi coupling
– Negishi alkynylation 46-301, 303
– Negishi conditions 43-235
– Negishi coupling 43-96, 100, 235, 359, 377, 45a-180, 227, 45b-586, 588–590, 627, 639, 1351, 1355, 1385, 46-257, 260, 276, 301, 331, 47a-68, 453–458, 461, 462, 909, 951, 956, 973, 978, 1004–1006, 1009, 48-51, 54, 57
– Negishi cross coupling 43-235, 254, 45a-242, 45b-584, 586–589, 639, 640, 647, 47a-453, 457, 461
– Negishi protocol 43-17
– Negishi reaction 43-13, 234f., 311, 45a-242, 45b-547, 584, 647, 648, 47a-453, 461, 48-29, 37, 51, 54
– Negishi reagent 46-253
– Negishi synthesis 45a-242
– Negishi-type cross coupling 45a-180, 47a-455
– Negishi-type reaction 43-234
– Negishi-type synthesis 47a-455
Negishi–Suzuki coupling
– Negishi–Suzuki tandem cross coupling 46-341
Nenitzescu compound
– Nenitzescu's hydrocarbon 47b-779
Nicholas reaction
– Nicholas reaction 43-14, 245f., 294
Nolan catalyst
– Nolan catalyst 46-99, 120
Noyori reaction
– Noyori's protocol 44-91
Nysted reaction
– Nysted reagent 46-74, 47a-204, 207, 208
O
Oppolzer cyclization
– Oppolzer cyclization 47b-747, 748
Otera's coupling
– Otera's double-elimination protocol 43-462
P
Paar–Knorr reaction
– Paar–Knorr reaction 45b-1291, 1292, 1294, 1295
Paterno–Büchi reaction
– Paterno–Büchi reaction 45a-349
Pauling scale
– Pauling electronegativity 47b-935
– Pauling scale 47b-929
Pauson–Khand reaction
– Pauson–Khand process 43-345
– Pauson–Khand reaction 44-7, 91, 366–368, 375, 45b-1029, 46-131, 217
– Pauson–Khand reaction, intramolecular 44-367
– Tandem Pauson–Khand reaction 44-367
Perkin reaction
– Perkin condensation 45a-217
– Perkin reaction 45a-217
– Perkin synthesis 45a-218
Petasis reaction
– Petasis alkenation 47a-220
– Petasis reagent 46-63, 69, 47a-1, 177, 178, 180–186, 188, 190, 194, 195, 197–204, 210, 220, 227
Petasis–Ferrier rearrangement
– Petasis–Ferrier rearrangement 47a-197
Peterson reaction
– Corey–Schlesinger–Mills modified Peterson alkenation 47b-910
– Peterson alkenation 43-13, 252, 462, 44-190f., 330f., 45a-215, 431, 437, 439, 444, 445, 458, 46-338, 341, 469, 647, 47a-1, 2, 85, 162, 910
– Peterson approach 47a-87
– Peterson elimination 43-461, 44-179, 46-469, 471
– Peterson elimination, vinylogous 46-53
– Peterson products 46-49
– Peterson reaction 43-24, 44-190, 45a-209, 215, 46-1, 2, 23, 46, 47, 63, 47a-85, 86, 88, 90, 100, 162
– Peterson reaction, vinylogous 46-53
– Peterson-type approach 44-175
– Peterson-type intermediate 47b-843
Phillips catalyst
– Phillips catalyst 48-701, 702
Pinacol coupling
– Pinacol coupling 47a-214
– Cyclization–pinacol cascade 48-670
– Cyclization–pinacol reaction 48-671
Prato reaction
– Prato reaction 45b-1130
Prins reaction
– Imino Prins reaction 44-388
– Prins addition 44-389
– Prins addition reaction 44-387
– Prins product 44-388
– Prins reaction 44-385–390
– Prins reaction, bimolecular 44-389
– Prins reaction, intramolecular 44-387f., 389
– Prins-pinacol cyclization 48-670
Pschorr reaction
– Pschorr cycliztion 45b-892
– Pschorr reaction 45b-892, 907
Q
Quinkert reaction
– Quinkert's procedure 46-616
R
Ramberg–Bäcklund reaction
– Ramberg–Bäcklund alkene synthesis 46-516
– Ramberg–Bäcklund approach 46-427
– Ramberg–Bäcklund method 43-449
– Ramberg–Bäcklund reaction 43-14, 16, 24, 253, 314, 321, 326, 328–330, 332, 448, 45b-1019, 46-427, 428, 516, 47a-8, 846, 847
– Ramberg–Bäcklund reaction, vinylogous 46-428, 429
– Ramberg–Bäcklund rearrangement 45b-1376, 1400, 1401
Reformatsky reaction
– Reformatsky reaction 43-491, 46-153
– Reformatsky reagent 47b-949
Reimer–Tiemann reaction
– Reimer–Tiemann conditions 45a-337
– Reimer–Tiemann product 45a-337, 341
– Reimer–Tiemann reaction 46-598
Reppe reaction
– Reppe cyclotetramerization 45a-394
– Reppe synthesis 46-131
– Reppe's discovery 45a-195
Rieke metal
– Rieke copper 48-88
– Rieke nickel 45a-534
– Rieke zinc 46-540, 48-59
Rieske dioxygenase
– Rieske dioxygenase 48-590
Ritter reaction
– Ritter reaction 44-338
Robinson annulation
– Robinson annulation 45b-1080, 48-667
Rosenmund reaction
– Rosenmund catalyst 46-528, 529, 541
Russig–Laatsch reaction
– Russig–Laatsch conditions 45b-934
S
Salmond reagent
– Salmond ylide 47a-49
Schlenck technique
– Schlenck technique 47b-1116
Schlosser reaction
– Wittig alkenation, Schlosser modification 47a-49
– Wittig reaction, Schlosser modification 46-28, 29, 47a-49
Schmidt reaction
– Schmidt reaction 45a-285
Schmittel cyclization
– Schmittel cyclization 45b-917
Scholl reaction
– Scholl reaction 45b-975, 976, 991, 1003
– Scholl-type reaction 45b-1118
Schrock catalyst
– Schrock carbene 45b-681, 46-102
– Schrock catalyst 46-115, 116, 47a-327, 355, 365, 367, 427
– Schrock complex 46-116
– Schrock-type carbene 45b-1428, 47a-162
– Schrock molybdenum catalyst 47a-394
– Schrock precatalyst 47a-387
– Schrock-type catalyst 47a-328
– Schrock-type complex 47a-328
Schulz–Flory distribution
– Schulz–Flory distribution 47a-551
Schwartz reagent
– Schwartz reagent 46-179, 47b-904, 48-377–379, 380, 381
SCOOPY reaction
– SCOOPY method 47a-62
– SCOOPY procedure 47a-61
– SCOOPY reaction 47a-61
– SCOOPY variant 47a-61
Scorpio catalyst
– Scorpio catalyst 47a-329
Scott procedure
– Scott's procedure 45b-1063
Seyferth–Gilbert reaction
– Seyferth–Gilbert alkynylation 43-383
– Seyferth–Gilbert method 43-18
– Seyferth–Gilbert modification 43-382
– Seyferth–Gilbert process 43-383
– Seyferth–Gilbert reagent 43-18, 382, 456
Shapiro reaction
– Shapiro protocol 47b-866, 868
– Shapiro reaction 46-468, 47a-5, 8, 853, 860, 861, 864, 866
– Shapiro-type reaction 47b-865
Sharpless oxidation
– Sharpless asymmetric dihydroxylation 46-630
– Sharpless procedure 47b-588
Shi reaction
– Shi asymmetric epoxidation 44-96f.
– Shi's protocol 48-523
Shirakawa method
– Shirakawa method 45b-1421
Shell Higher Order Process
– Shell Higher Order Process (SHOP) 48-706
Sigmatropic rearrangement
– [1,3]-Sigmatropic rearrangement 43-328, 47b-1089
– [1,3]-Sigmatropic shift 47b-1089
– [2,3]-Sigmatropic rearrangement 43-495, 47b-1084, 1085
– [3,3]-Sigmatropic rearrangement 43-25, 269, 317, 322, 471f., 474, 47b-1077, 1086, 1087
Simmons–Smith reaction
– Simmons–Smith conditions 48-512
– Simmons–Smith cyclopropanation 48-509, 517–523, 527, 528, 533, 535, 543, 544
– Simmons–Smith cyclopropanation, one-step 48-532
– Simmons–Smith methodology 48-517
– Simmons–Smith protocol 48-533
– Simmons–Smith reaction 48-6, 517, 518, 523
– Simmons–Smith reagent 46-73, 48-523, 533, 535
– Simmons–Smith-type cyclopropanation 48-517
Skattebøl reaction
– Skattebøl reaction 44-175
Smiles rearrangement
– Smiles rearrangement 45b-1366, 47a-143, 151
Sommelet–Hauser reaction
– Thia-Sommelet–Hauser dearomatization 46-599
Sonogashira coupling
– Sonogashira alkynylation 43-227
– Sonogashira conditions 43-65, 82, 226f., 360f., 363
– Sonogashira coupling 43-6, 16f., 65, 75, 369, 44-445, 45a-399, 403, 424, 45b-875, 1221, 1222, 1351, 1358, 1359, 46-327, 642, 47b-889
– Sonogashira cross coupling 43-12, 65, 226, 345, 361, 366, 371
– Sonogashira modification of the Heck reaction 46-302
– Sonogashira protocol 43-350, 361, 363, 364, 366, 368
– Sonogashira reaction 43-225–227, 311, 349, 350, 359, 360, 362–366, 368–370, 373, 374, 44-232, 45a-203
– Sonogashira-like coupling 43-368
– Sonogashira-like reaction 43-373
– Sonogashira-type alkynylation 44-313
– Sonogashira-type coupling 43-64, 368
– Sonogashira-type cross coupling 43-357, 364, 44-132, 159f.
– Sonogashira-type reaction 43-234, 349, 359, 361, 371
– Tandem Sonogashira–benzannulation 45a-203
Sonogashira–Hagihara coupling
– Sonogashira–Hagihara coupling 43-352
– Sonogashira–Hagihara cross coupling 43-359
– Sonogashira–Hagihara reaction 43-19
Stetter reaction
– Stetter reaction 48-669
Stevens rearrangement
– Stevens rearrangement 45b-946, 1334–1336
Stevens–Castro reaction
– Stevens–Castro conditions 43-225
– Stevens–Castro coupling 43-396
– Stevens–Castro cross coupling 43-345
– Stevens–Castro process 43-13
– Stevens–Castro reaction 43-19, 225, 240, 325, 345, 351f., 359, 396f.
– Stevens–Castro route 43-17
Stille coupling
– Stille conditions 43-232
– Stille coupling 43-13, 16f., 232, 45a-81, 403, 45b-577–579, 581–583, 627, 641, 664, 665, 689, 1055, 1221, 1222, 1351–1354, 1357, 1360, 1368, 1382–1384, 1386, 46-642, 47a-447–449, 910
– Stille cross coupling 43-254, 44-158, 45a-182, 241, 45b-551, 577–582, 641, 664, 47a-447–449
– Stille protocol 43-17, 46-257
– Stille reaction 43-311, 44-159, 45b-547, 1351, 47a-448, 449
– Stille synthesis 45a-241
– Stille-type coupling 43-233, 349, 44-6, 313, 45b-985
– Stille-type cross coupling 45a-181
– Stille-type reaction 43-233
Still–Gennari reaction
– Still–Gennari alkenation 46-339, 341, 47a-68
– Still–Gennari modification 47a-68
– Still–Gennari modification of Horner–Emmons
protocol 47a-61
– Still–Gennari modification of Horner–Emmons
reaction 47a-68
– Still–Gennari modification of the Horner–Wadsworth–Emmons reaction 46-43, 44, 46, 278
– Still–Gennari reaction 46-332
– Still–Gennari variation of the Horner–Wadsworth–Emmons reaction 46-40
Stobbe reaction
– Stobbe reaction 46-166–168
Stork procedure
– Stork procedure 45b-1352
Stork–Zhao reaction
– Stork–Zhao alkenation 47a-68
– Stork–Zhao modification 47a-68
– Stork–Zhao modification of Wittig protocol 47a-61
– Stork–Zhao Wittig reaction 47a-68
Suda method
– Suda method 48-512
Suzuki coupling
– Suzuki arylation 45b-558
– Suzuki coupling 43-16, 67, 363, 45a-173, 175, 176, 403, 45b-550, 552, 553, 557–559, 564, 571–573, 627, 638, 644–646, 661–663, 671, 672, 966, 972, 974, 978, 1033, 1351, 1356, 1357, 1386, 1387, 46-299, 47a-68, 442, 461, 47b-889, 909, 978, 1004
– Suzuki cross coupling 45b-551–553, 555–557, 562–569, 571, 572, 575, 577, 638, 644, 661, 47a-445, 446, 48-4
– Suzuki reaction 43-311, 45b-547, 555, 559, 576, 645, 47a-442
– Suzuki version 46-257
Suzuki–Heck coupling
– Suzuki–Heck-type coupling 45b-987
Suzuki–Miyaura coupling
– Suzuki–Miyaura coupling 45a-175, 176, 227, 238, 45b-815, 896, 898, 899, 1055, 1155, 1221, 1222, 1261, 1269, 47a-440, 442–444, 460, 48-64, 65, 69
– Suzuki–Miyaura cross coupling 43-13, 228f., 380f., 45a-197, 45b-783, 46-178, 192, 47a-553
– Suzuki–Miyaura reaction 45a-175, 237, 47a-442, 48-3, 29, 37, 63–71
– Suzuki–Miyaura synthesis 45a-237, 238
Swern oxidation
– Swern oxidation 45a-371, 45b-838
– Swern protocol 44-320
– Swern reagent 47a-33
T
Takahashi reaction
– Takahashi reagent 46-253, 254
Takai reaction
– Takai alkenation 47a-235
– Takai reaction 47a-235
– Takai's homologation 45b-1352
Takai–Nozaki reaction
– Takai–Nozaki reagent 47a-206, 212
Takai–Ohshima reaction
– Takai–Ohshima conditions 47a-209
– Takai–Ohshima procedure 46-75
– Takai–Ohshima reagent 47a-208
Takai–Utimoto reaction
– Takai–Utimoto protocol 47a-232
– Takai–Utimoto reagent 47a-205, 210
Takeda reaction
– Takeda alkenation 47a-227, 230
Tamao–Kumada–Corriu reaction
– Tamao–Kumada–Corriu process 45a-243
– Tamao–Kumada–Corriu reaction 45a-227, 243
Tebbe reaction
– Tebbe alkenation 44-212
– Tebbe methylenation 46-65–68
– Tebbe reagent 46-3, 4, 63–69, 72, 47a-1, 162–177, 179, 183, 188, 191, 199, 200, 216, 220, 227, 974, 48-428
– Tebbe-like derivative 47a-232
Thorpe–Ingold effect
– Thorpe–Ingold effect 47a-412
Tiffeneau–Demjanov reaction
– Tiffeneau–Demjanov ring expansion 45a-366, 45b-1065
Tipson–Cohen reaction
– Tipson–Cohen reaction 47b-838
Toyooka reaction
– Toyooka endgame sequence 47a-25
Tsuji–Trost reaction
– Tsuji–Trost reaction 43-311, 46-313
– Tsuji–Trost-type α-allylation 47a-519
U
Ugi reaction
– Ugi condensation 45a-303
Ullmann reaction
– Ullmann coupling 45b-547–549, 820, 821, 863, 864, 1362
– Ullmann homocoupling 45b-548
– Ullmann protocol 45b-547
– Ullmann reaction 45b-547, 653, 654, 999, 1000
– Ullmann-type coupling 45b-655
Umpolung
– umpoled 43-17
Urushibara nickel catalyst
– Urushibara nickel catalyst 48-296, 297
V
Vaska's complex
– Vaska's complex 44-366, 48-344
Verkade superbase
– Verkade superbase 43-49
Vilsmeier reaction
– Vilsmeier complex 45a-450
– Vilsmeier formylation 45a-309
– Vilsmeier reaction 45b-816, 1091
– Vilsmeier reagent 45a-450
W
Wacker reaction
– Wacker-type carboxypalladation 46-327
Wagner–Meerwein rearrangement
– Wagner–Meerwein rearrangement 45b-907
– Wagner–Meerwein shift 45a-160
Weinreb amide
– Weinreb amide 44-88, 47a-37
– Weinreb enamide 44-364
Wessely oxidation
– Wessely oxidation 46-609, 610, 615, 617, 621
– Wessely reaction 46-609, 610
Wharton rearrangement
– Wharton rearrangement 48-113, 114
Wilkinson's catalyst
– Wilkinson's catalyst 43-277, 45a-423, 46-197, 230, 47a-218, 379, 1059, 48-268, 271, 342, 344, 345, 347, 348, 351, 364, 440, 648, 681
– Wilkinson's complex 46-225, 48-440, 441
– Wilkinson-type catalyst 48-342
Williamson etherification
– Williamson etherification 45b-1210, 1225, 1233, 1240, 1248, 1262
Wittig reaction
– Boron-Wittig transformation 44-203
– Double Wittig reaction 44-24f., 47f.
– Silyl-Wittig reaction 45a-431
– Tandem-oxidation–Wittig reaction 46-34
– Thioester reduction–Wittig alkenation 47a-39
– Wittig alkenation 43-13, 18, 38, 79, 249, 376, 380, 44-330, 45a-212, 431, 45b-575, 576, 1396, 46-326, 647, 47a-2, 20, 21, 26–30, 33–45, 49, 53, 54, 61, 69, 71, 162, 843, 1135
– Wittig alkenation, Corey–Fuchs-type 43-100
– Wittig alkenation, intramolecular 47a-70
– Wittig alkenylation 43-76
– Wittig chemistry 46-24
– Wittig conditions 45a-85, 46-28
– Wittig elimination, one-pot 43-445
– Wittig methylenation 47a-22, 24
– Wittig preparation, butatriene 44-46f.
– Wittig procedure, one-pot 43-444
– Wittig procedure, Schlosser modification 47a-49
– Wittig product 45b-1370
– Wittig protocol, Stork–Zhao modification 47a-61
– Wittig reaction 43-24, 250, 254, 434, 454, 455, 472, 44-4, 24f., 25, 46f., 49, 207, 214, 45a-209–211, 215, 355, 393, 409, 419, 431, 487, 522, 45b-686, 687, 755, 911, 923, 925, 966, 1080, 1316, 1317, 1350, 1369, 1370, 1381, 1396, 1397, 46-1, 23, 24, 26, 28, 31, 32, 35, 37, 63, 82, 239, 257, 332, 370, 47a-1, 21, 27, 31, 32, 42, 49, 54, 56, 58, 63, 87, 162, 1135, 1136
– Wittig reaction, intramolecular 45b-1081
– Wittig reaction, oxidative 47b-1136
– Wittig reagent 45b-838, 1370, 1371, 46-35, 82, 47a-168, 183, 207
– Wittig ring-contraction reaction 43-313
– Wittig route 43-380
– Wittig salt 45b-1396
– Wittig sequence 48-678
– Wittig synthesis 43-79f., 45a-211, 47a-28
– Wittig ylide 44-24, 45b-1370
– Wittig-like reaction 46-65
– Wittig-type alkenation 44-437
– Wittig-type approach 44-175
– Wittig-type methylenation 46-70, 71, 47a-162
– Wittig-type reaction 44-203, 208, 46-23, 47b-161, 1135
– Wittig-type strategy 46-158, 168
Wittig rearrangement
– [2,3] Wittig rearrangement 44-294
– Wittig rearrangement 43-295, 45a-417, 45b-1333, 1334
Wittig–Horner reaction
– Wittig–Horner alkenation 43-13, 47a-46, 47, 50, 51, 64
– Wittig–Horner reaction 45a-391, 409, 47a-46, 49, 50, 54
– Wittig–Horner synthesis 47a-65
– Wittig–Horner transformation 43-13
– Wittig–Horner-type alkenation 43-382
– Wittig–Horner-type process 43-18
Wittig–Horner–Emmons reaction
– Wittig–Horner–Emmons reaction 43-249, 250
Wittig–Schlosser reaction
– Wittig–Schlosser alkenation 47a-49
– Wittig–Schlosser reaction 47a-54
Wittig–Wadsworth–Emmons reaction
– Wittig–Wadsworth–Emmons alkenation 43-18
Wolff rearrangement
– Photo-Wolff rearrangement 45a-265, 266, 45b-1305
– Wolff rearrangement 45b-1048, 1276, 1277, 48-687, 689
Wolff–Kishner reduction
– Kishner conditions 48-125
– Kishner procedure 48-129
– Wolff–Kishner conditions 45a-184, 185, 45b-921, 48-196
– Wolff–Kishner deoxygenation 48-125
– Wolff–Kishner method 48-139, 140
– Wolff–Kishner procedure 48-98, 638
– Wolff–Kishner reaction 45a-185, 45b-778, 787, 816, 824, 832, 870, 873, 48-163, 638
– Wolff–Kishner reduction 45a-184–187, 45b-1298, 1299, 48-4, 97, 111–114, 117, 120, 125, 140, 141
– Wolff–Kishner reduction, Barton modification 48-112, 117
– Wolff–Kishner reduction, Cram–Henbest modification 48-112, 119
– Wolff–Kishner reduction, Furrow–Myers modification 48-112, 123
– Wolff–Kishner reduction, Huang–Minlon modification 48-97, 112, 114
– Wolff–Kishner reduction, Nagata–Itazaki modification 48-112, 121, 122
Woodward–Hoffmann rules
– Woodward–Hoffmann rules 45a-347, 46-385, 389, 401, 413, 426, 433, 435
Wurtz coupling
– Wurtz coupling 43-22, 45b-1321, 48-3, 29, 88, 89
– Wurtz cyclization 45b-907
– Wurtz reaction 48-87, 88
– Wurtz–Grignard reaction 48-88
– Wurtz-type coupling 43-393f.
– Wurtz-type reaction 43-635
Wurtz–Fittig reaction
– Wurtz–Fittig dehalogenation 45b-698, 715, 716
– Wurtz–Fittig reaction 45b-653, 654, 698
Y
Yamaguchi reaction
– Yamaguchi esterification 46-138
Yamamoto reagent
– Yamamoto reagent 44-246
Z
Zaitsev rule
– Hofmann/Zaitsev ratio 47b-795, 796
– Zaitsev product 47b-781, 796
– Zaitsev rule 47b-781
Zeise salt
– Zeise salt 48-595
Ziegler catalyst
– Ziegler catalyst 48-428, 699, 702, 708–710, 718, 719, 723, 730
– Ziegler system 48-702
– Ziegler–Natta system 48-702
– Ziegler-type catalyst 43-428, 45b-1336, 48-342
Ziegler–Hafner synthesis
– Ziegler–Hafner method 45b-1084
– Ziegler–Hafner route 45b-1072
– Ziegler–Hafner synthesis 45b-1084
Ziegler–Natta catalyst
– Ziegler–Natta catalyst 45b-1422, 48-695, 699–701, 709, 716, 724, 726, 727, 730
– Ziegler–Natta catalyst, first generation 48-699, 700, 720
– Ziegler–Natta catalyst, second generation 48-700, 720
– Ziegler–Natta catalyst, third generation 48-701
– Ziegler–Natta-type catalyst 48-728
Ziegler–Natta polymerization
– Ziegler–Natta 45b-733
– Ziegler–Natta polymerization 45b-666
– Ziegler-type catalyst 45b-776
Zipper reaction
– Acetylene zipper 43-26, 503f.
– Zipper reaction 43-26, 82
In this cumulative index for Volumes 43–48, which should be used in conjunction with the Tables of Contents of the individual volumes, starting materials are indicated in an italic font, products are identified by an arrow (→), and all other entries are given in a roman font.
A
→ Aceanthrylenes, from cycloaddition of anthracenes with alkynes, zirconium mediated 45b-1023
→ Aceanthrylenes, from cycloaddition of 9-bromoanthracenes with terminal alkynes, palladium catalyzed 45b-1023, 45b-1024
→ Aceanthrylenes, from pyrolysis of 9-ethynylanthracene 45b-1022, 45b-1023
Acecorannulenes – see Acenaphth[3,2,1,8-lmnoa]acephenanthrylenes
→ Acenaphth[3,2,1,8-lmnoa]acephenanthrylenes, 8,9-dihydro-, from intramolecular Stille-type coupling of 1,10-bis(bromomethyl)dibenzo[ghi,mno]fluoranthenes, using hexamethyldistannane, palladium catalyzed 45b-985
→ Acenaphth[3,2,1,8-lmnoa]acephenanthrylenes, from reductive ring closure of 1,3,4,6,7,10-hexakis(dibromomethyl)fluoranthenes, using various reagents 45b-984
Acenaphthoquinones, Knoevenagel condensation with ketones, then dehydration, Diels–Alder cycloaddition with alkenes, and decarbonylation–dehydrogenation using palladium/charcoal, fluoranthene synthesis45b-1029, 45b-1030
Acenaphthylenes, 1,2-bis(silylethynyl)-, cycloaromatization, tellurium mediated, fluoranthene synthesis45b-1035, 45b-1036
Acenaphthylenes, cycloaddition with alkynes, cobalt catalyzed, tetracyclic fused cyclobutene synthesis47b-890, 47b-891
Acenaphthylenes, Diels–Alder cycloaddition with butadienes, then dehydrogenation using palladium/barium sulfate, fluoranthene synthesis45b-1031, 45b-1032
Acenaphthylenes, Diels–Alder cycloaddition with 1,3-diphenylbenzo[c]furan, 7,12-diphenylbenzo[k]fluoranthene synthesis45b-1037, 45b-1038
→ Acenaphthylenes, from annulation of 1,8-diiodonaphthalenes with alkynes, palladium catalyzed 45b-1020, 45b-1021
→ Acenaphthylenes, from 1,2-dihydroacenaphthylenes, using various methods 45b-1018, 45b-1019
→ Acenaphthylenes, from Ramberg–Bäcklund reaction of 1,3-dibromonaphtho[1,8-cd]thiopyran 2,2-dioxides with sodium methoxide 45b-1019, 45b-1020
Acenaphthylen-5-ones, 4-diazo-2,4-dihydro, photolytic Wolff rearrangement, then gas-phase dehydrogenation–decarboxylation using palladium/carbon, cyclopenta[cd]indene synthesis45b-1048
Acenes, angular, atypical 45b-885, 45b-886
→ Acenes, angular, synthesis by photodehydrocyclization, ring-closing alkene metathesis, or cycloisomerization 45b-946–45b-948
Acetaldehydes, (indan-1-yl)-, decarbonylation, rhodium catalyzed, 1-methylindane synthesis48-440
Acetaldehydes, phenyl-, cyclization with alkynes, titanium catalyzed, substituted naphthalene synthesis45b-750
