Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Edition

by Richard C. Larock
Edition: 2nd
Format: Hardcover
Pub. Date: 1999-11-01
Publisher(s): Wiley-VCH
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Summary

This long-awaited, greatly-expanded new edition of a best-selling guide offers an encyclopedic and systematic collection of useful synthetic methodology, including tens of thousands of reactions and synthetic transformations. The first edition has been reviewed in the professional journals as "clearly...the first choice for researchers seeking information on synthetic transformations." And as "useful to anyone who must do organic synthesis, especially those whose focus is not strictly organic chemistry. It provides a...clear road map to the synthetic literature and should be kept within easy reach of the chemist's desk."

Table of Contents

Literature Abbreviations xxxv
Chemical Abbreviations xli
ALKANES AND ARENES 1(2)
GENERAL REFERENCES 3(212)
Reduction
5(72)
Cyclic Alkanes
5(2)
Arenes
7(1)
Alkenes
7(21)
Catalytic Hydrogenation
7(5)
Diimide Reduction (HN=NH)
12(1)
Hydroboration--Protonolysis
12(1)
Metal Hydrides
12(1)
Miscellaneous Reagents
13(1)
Conjugate Reduction
13(15)
Reductive Dimerization
28(1)
Alkynes
28(1)
Catalytic Hydrogenation
28(1)
Hydroalumination--Protonolysis
28(1)
Miscellaneous Reagents
28(1)
Organic Halides
29(10)
Low-Valent Metals
29(1)
Metal Hydrides
30(4)
Miscellaneous Reagents
34(5)
Amines and Derivatives
39(2)
Nitro Compounds
41(1)
Ethers
42(2)
Alcohols and Phenols
44(9)
Direct Reduction
44(2)
Via Phosphorus Compounds
46(1)
Via Sulfonates
47(2)
Via Other Derivatives
49(4)
Sulfur Compounds
53(7)
Selenium Compounds
60(1)
Aldehydes and Ketones
61(7)
Direct Reduction
61(3)
Via Hydrazones
64(1)
Via Oxygen and Sulfur Derivatives
65(1)
Via Selenium Derivatives
65(1)
Decarbonylation
65(2)
Ketone Cleavage
67(1)
Reductive Coupling
67(1)
Acetals
68(1)
Carboxylic Acids
68(2)
Acid Halides
70(1)
Esters and Lactones
70(5)
Nitriles
75(1)
Isonitriles
76(1)
Coupling Reactions
77(52)
Symmetrical or Intramolecular Coupling
77(11)
Unsymmetrical Coupling
88(41)
Organolithium Reagents
88(12)
Organosodium or -Potassium Compounds
100(1)
Grignard Reagents
101(3)
Organoboron Reagents
104(2)
Organoaluminum Reagents
106(1)
Organothallium Reagents
107(1)
Organosilicon Reagents
108(1)
Organogermanium Reagents
109(1)
Organotin Reagents
109(2)
Lead Reagents
111(1)
Sulfur Reagents
111(1)
Selenium Reagents
112(1)
Tellurium Reagents
113(1)
Phosphorus Reagents
113(1)
Organotitanium and -zinc Reagents
113(1)
Organozirconium Reagents
114(1)
Vanadium Reagents
114(1)
Organochromium Reagents
115(1)
Organomanganese Reagents
116(1)
Organoiron Reagents
116(1)
Organonickel Reagents
116(1)
Organopalladium Reagents
117(1)
Organocopper Reagents
118(4)
Organosilver Reagents
122(1)
Organozinc Reagents
122(2)
Organomercury Reagents
124(1)
Miscellaneous Reagents
125(4)
Friedel--Crafts and Related Alkylation Reactions
129(6)
Ring-Forming Reactions
135(52)
Three-Membered Rings
135(26)
Four-Membered Rings
161(7)
Five-Membered Rings
168(6)
Six-Membered Rings
174(1)
Various Ring Sizes
175(10)
Carbocationic Cyclization
185(1)
Polycyclics
185(2)
Aromatization
187(28)
Dehydrogenation
187(4)
Elimination
191(2)
Reductive Elimination
193(2)
Rearrangement
195(1)
Cyclization and Annulation
196(11)
Diels-Alder and Related Reactions
207(8)
ALKENES 215(2)
GENERAL REFERENCES 217(346)
Isomerization of Alkenes
219(32)
Alkene Inversion
219(1)
Simple Rearrangement
220(7)
Thermal
220(1)
Photochemical
220(1)
Cation Radical
221(1)
Base-Promoted
222(1)
Acid-Catalyzed
223(1)
Sulfur Dioxide
223(1)
Ene Reaction--Reduction
223(1)
Iodine
223(1)
Transition Metal-Catalyzed
223(3)
Organoboranes
226(1)
Trimethylsilyl Chloride
226(1)
Addition--Elimination
227(1)
Functional Group Rearrangement
227(2)
Reductive Transposition
229(2)
Oxidative Transposition
231(3)
Metal and Heteroatom Displacement
234(2)
Ene Reaction
236(1)
Alkylative Transposition
236(15)
Elimination
251(66)
Dehydrogenation
251(5)
Dehydrohalogenation of Alkyl Halides
256(2)
1,1-Dihalides
258(1)
1,2-Dihalides
259(4)
1,3-Dihalides
263(1)
β-Halo Ethers
263(3)
Halohydrins
266(1)
β-Halo Esters
267(1)
β-Halo Sulfonates
268(1)
Amines
268(1)
β-Halo Amines
269(1)
Amine Oxides (Cope Elimination)
269(1)
Quaternary Ammonium Salts
269(1)
N-Alkyl-N,N-disulfonimides
270(1)
N-Nitrosocarboxamides
270(1)
Nitro compounds
270(1)
Diazo Compounds
271(1)
β-Substituted Azides
272(1)
Ethers
272(5)
β-Substituted Ethers
277(1)
Sulfides
278(1)
α-Halosulfides
279(1)
β-Halosulfides
279(1)
β-Hydroxysulfides
279(1)
Sulfoxides
280(1)
β-Hydroxysulfoxides
281(1)
Sulfones
281(2)
α-Halosulfones (Ramberg-backlund Reaction)
283(1)
β-Hydroxysulfones
283(1)
β-Acyloxysulfones
284(1)
Other β-Substituted Sulfones
285(1)
Disulfones
286(1)
Sulfonyl Halides
286(1)
β-Oxyselenides
286(1)
Selenoxides
287(3)
Tellurides
290(1)
Organosilanes
290(1)
β-Halosilanes
290(1)
β-Oxysilanes and -Stannanes
291(1)
β-Aminosilanes
291(1)
Dehydration of Alcohols
291(3)
Sulfonate Esters
294(1)
Sulfates
295(1)
Phosphates and Thiophosphates
295(1)
Xanthates
296(1)
Thiocarbonates
296(1)
Carbamates
297(1)
N-Methyl-4-alkoxypyridinium lodides
297(1)
1,2-Diols and Derivatives
297(3)
Stereospecific Cis Elimination
297(1)
Nonstereospecific or Unknown Stereochemistry
298(2)
1,2-Disulfonates
300(1)
1,3-Diols
300(1)
Acetals
300(1)
Dithioacetals
300(1)
Aldehydes and Ketones
301(8)
Direct Elimination
301(1)
Arenesulfonylhydrazone Eliminations
301(2)
Enone Conversions
303(1)
Reduction of Carbonyl Derivatives
304(1)
Dimerization of Aldehydes and Ketones
305(3)
Miscellaneous Reactions
308(1)
Lactols
309(1)
Carboxylic Acids
309(2)
Acid Halides
311(1)
Acid Anhydrides
312(1)
Esters and Lactones
312(2)
Thioesters
314(1)
Amides and Lactams
314(1)
Imides
315(1)
Nitriles
315(1)
Miscellaneous Reactions
315(2)
Alkylidenation of Carbonyl and Related Compounds
317(10)
Wittig and Related Reactions
327(24)
Wittig Reaction
327(5)
General
327(1)
Intramolecular Wittig
328(1)
Mechanism
328(1)
Miscellaneous Reactions
328(4)
β-Oxido Ylids
332(1)
Ylid Anions
332(1)
Phosphonates
332(2)
General
332(1)
Intramolecular
333(1)
Miscellaneous Reactions
333(1)
Phosphonamidates [(R2N)(RO)POCHLiR]
334(1)
Phosphonic Acid bis Amides [(R2N)2POCHLiR]
334(1)
Phosphinothioic Amides [PhPS(NR2)CHLiR]
334(1)
Phosphine Oxides
335(1)
Arsenic Ylids
335(1)
Sulfur Reagents
336(1)
Selenium Reagents
336(1)
Tellurium Reagents
337(1)
Boron Reagents
337(1)
Peterson Reaction (Oxysilane Elimination) and Related Reactions
337(4)
Isonitriles
341(1)
Miscellaneous Reactions
341(10)
Metal-Promoted Coupling Reactions
351(52)
Alkali Metal Reagents
351(8)
Grignard Reagents
359(3)
Boron Reagents
362(2)
Aluminum Reagents
364(1)
Indium Reagents
364(1)
Thallium Reagents
365(1)
Silicon Reagents
365(8)
Germanium Reagents
373(1)
Tin Reagents
373(5)
Sulfur Reagents
378(1)
Selenium Reagents
379(1)
Tellurium Reagents
379(1)
Titanium Reagents
379(1)
Zirconium Reagents
379(1)
Molybdenum Reagents
380(1)
Manganese Reagents
380(1)
Iron Reagents
380(1)
Ruthenium Reagents
381(1)
Cobalt Reagents
381(1)
Nickel Reagents
382(4)
Palladium Reagents
386(6)
Copper Reagents
392(7)
Silver Reagents
399(1)
Zinc Reagents
399(1)
Mercury Reagents
400(1)
Olefin Metathesis
401(2)
Arene, Alkyne and Diene Addition Reactions
403(60)
Hydrogen Addition
403(7)
Alkylation and Functionalization
410(53)
Thermal or Lewis Acid-Promoted
410(3)
Photochemical
413(1)
Free Radical
413(5)
Michael Additions
418(1)
Organolithium Compounds
419(1)
Organomagnesium Compounds
420(1)
Organocalcium Compounds
421(1)
Organoboron Compounds
421(6)
Organoaluminum Compounds
427(5)
Organosilicon Compounds
432(2)
Organotin Compounds
434(3)
Organsulfur and -selenium Compounds
437(1)
Organotellurium Compounds
438(1)
Organotitanium Compounds
438(2)
Organozirconium Compounds
440(3)
Organotantalum Compounds
443(1)
Organochromium and -tungsten Compounds
444(1)
Organomanganese Compounds
444(1)
Organoiron Compounds
445(1)
Organoruthenium Compounds
445(1)
Organoosmium Compounds
446(1)
Organocobalt Compounds
446(1)
Organorhodium Compounds
446(1)
Organoiridium Compounds
447(1)
Organonickel Compounds
447(1)
Organopalladium Compounds
448(4)
Organopalladium and -platinum Compounds
452(1)
Organocopper Compounds
452(8)
Organosilver Compounds
460(1)
Organozinc Compounds
460(1)
Organomercury Compounds
461(1)
Miscellaneous Reagents
461(2)
Dienes and Polyenes
463(60)
Rearrangement
463(3)
Elimination Reactions
466(9)
Organometallic Approaches
475(41)
Organolithium and -sodium Compounds
475(1)
Organomagnesium Compounds
476(3)
Organobarium Compounds
479(1)
Organoboron Compounds
479(3)
Organoaluminum Compounds
482(2)
Organoindium Compounds
484(1)
Organosilicon Compounds
484(3)
Organotin Compounds
487(3)
Sulfur Reagents
490(1)
Tellurium Reagents
491(1)
Phosphorus Reagents
492(1)
Organotitanium Compounds
493(1)
Organozirconium Compounds
494(2)
Organoniobium Compounds
496(1)
Organochromium Compounds
496(1)
Organoiron Compounds
497(1)
Organoruthenium Compounds
498(1)
Organocobalt Compounds
499(1)
Organorhodium Compounds
499(1)
Organonickel Compounds
499(2)
Organopalladium Compounds
501(5)
Organocopper Compounds
506(7)
Organosilver Compounds
513(1)
Organozinc Compounds
514(1)
Organomercury Compounds
515(1)
Arene Conversions
516(2)
Cyclization
518(4)
Miscellaneous Reactions
522(1)
Diels-Alder Reactions
523(22)
General Reviews
523(1)
Regioselectivity
523(1)
Exo/Endo Selectivity
524(1)
Asymmetric Diels-Alder Reaction
524(4)
Reviews
524(1)
Regular Diels-Alder Reaction
525(2)
Inverse Electron-Demand Diels-Alder Reaction
527(1)
Hetero Diels-Alder Reaction
527(1)
Mechanism
528(1)
Use of High Pressure
528(1)
Microwave Irradiation
528(1)
Ultracentifugation
528(1)
Use of Ultrasound
528(1)
Catalysis
528(2)
Solvent Effects
530(1)
Retro-Diels-Alder Reaction
530(1)
Intramolecular Diels-Alder Reaction
530(2)
Inverse Electron-Demand Diels-Alder Reaction
532(1)
Radical Cation Diels-Alder Reaction
532(1)
Ionic Diels-Alder Reaction
532(1)
Use of Heterodienophiles
533(1)
Use of Heteroatom-Containing Dienes
533(1)
Use of substituted 1,3-Dienes
534(2)
Heteroatom-substituted 1,3-Dienes
534(1)
Carbon-Substituted 1,3-Dienes
535(1)
o-Quinodimethanes and Heterocyclic Analogues
536(1)
Arynes
537(1)
Some Other Dienophiles
537(4)
Dienophile Equivalents
541(3)
Transition Metal Carbenes as Dienophiles
544(1)
Cyclization, Annulation and Related Reactions
545(16)
Three-Membered Rings
545(1)
Four-Membered Rings
546(1)
Five-Membered Rings
547(9)
Six-Membered Rings
556(2)
Seven-Membered Rings
558(1)
Eight-Membered Rings
559(1)
Nine-Membered Rings
559(1)
Various-Membered Rings
559(2)
Miscellaneous Reactions
561(2)
ALKYNES 563(2)
GENERAL REFERENCES 565(42)
Isomerization
567(2)
Elimination Reactions
569(12)
Wittig and Related Approaches
581(4)
Alkylation, Alkenylation and Arylation of Alkynes and Allenes
585(22)
Organolithium, -sodium and -magnesium Compounds
585(4)
Organoboron Compounds
589(1)
Organoaluminum Compounds
590(1)
Organothallium Compounds
591(1)
Organosilicon Compounds
591(1)
Organotin Compounds
592(2)
Organozirconium Compounds
594(1)
Organocobalt Compounds
594(2)
Organonickel Compounds
596(1)
Organopalladium Compounds
596(3)
Organocopper Compounds
599(5)
Organozinc Compounds
604(1)
Organomercury Compounds
604(1)
Organosamarium Compounds
604(1)
Miscellaneous Reactions
605(2)
HALIDES 607(2)
GENERAL REFERENCES 609(144)
Halogenation of Hydrocarbons
611(8)
Aliphatic Halogenation
611(3)
Allylic Halogenation
614(1)
Benzylic Halogenation
615(4)
Aromatic Halogenation
619(10)
Halogenation of Alkenes
629(26)
Halogen Addition
629(4)
Hydrohalogenation
633(3)
Markovnikov Addition
633(2)
Anti-Markovnikov Addition
635(1)
Unknown Regiochemistry
636(1)
Isomerization--Addition
636(1)
Hydrogen Substitution
636(2)
Halofunctionalization
638(9)
Haloalkylation
647(6)
Miscellaneous Reactions
653(2)
Halogenation of Alkynes
655(12)
Interconversion of Halides
667(10)
Aliphatic Halides
667(4)
Vinylic Halides
671(1)
Aromatic Halides
671(1)
Homologation of Halides
672(2)
Rearrangement of Halides
674(3)
Halogenation of Nitrogen Compounds
677(8)
Halogenation of Ethers
685(4)
Halogenation of Alcohols
689(14)
Direct Methods
689(8)
Via Sulfonates
697(3)
Via Haloformates
700(1)
Other Approaches
701(1)
Diols
701(2)
Halogenation of Phenols
703(2)
Halogenation of Sulfur and Selenium Compounds
705(4)
Halogenation of Carbonyl and Related Compounds
709(32)
Aldehydes and Ketones
709(18)
Acetals
727(3)
Lactols
730(1)
Carboxylic Acids
730(1)
Acid Halides
731(1)
Esters and Lactones
732(4)
Amides
736(3)
Imides and Related Compounds
739(1)
Nitriles
739(2)
Halodecarboxylation and Decarbonylation of Acids and Derivatives
741(4)
Halogenation of Organometallics
745(8)
AMINES 753(2)
GENERAL REFERENCES 755(126)
From Alkanes
757(2)
From Arenes
759(2)
From Alkenes, Dienes and Alkynes
761(18)
From Alkyl and Aryl Halides or Sulfonates
779(6)
From Other Amines and Derivatives
785(30)
Reduction
785(4)
Alkylation on Nitrogen
789(3)
Alkylation on Carbon
792(10)
Ring Opening
802(5)
Dealkylation
807(3)
Rearrangement
810(5)
From Azides
815(6)
From Nitro Compounds
821(8)
Heteroatom and Metal Displacement
829(2)
From Ethers, Alcohols and Derivatives
831(4)
From Aldehydes, Ketones and Derivatives
835(32)
Transamination
835(1)
Reductive Amination
835(12)
Alkylative Amination
847(16)
Mannich and Related Reactions
863(2)
α-Amination
865(1)
Miscellaneous Reactions
866(1)
From Carboxylic Acids and Derivatives
867(8)
Molecular Rearrangements
867(2)
Hoffman
867(1)
Curtius
868(1)
Lossen
869(1)
Schmidt
869(1)
Miscellaneous
869(1)
Reduction of Amides and Imides
869(3)
Reductive Alkylation
872(2)
Substitution
874(1)
From Nitriles
875(4)
From Isonitriles
879(2)
ETHERS 881(2)
GENERAL REFERENCES 883(76)
From Other Ethers
885(4)
Alkylation of Alcohols and Phenols
889(22)
Alkane, Arene, Alkene and Alkyne Additions and Substitutions
911(20)
Alkane Substitution
911(1)
Arene Addition and Substitution
911(1)
Alkene Substitution
912(1)
Alkene Addition
912(3)
Expoxidation of Alkenes
915(12)
Diene Addition
927(1)
Alkyne Addition
928(3)
Acetal, Carbonyl and Ortho Ester Conversions
931(26)
Acetals
931(11)
Aldehydes and Ketones
942(9)
Lactols
951(2)
Carboxylic Acids
953(1)
Esters and Lactones
953(3)
Peresters
956(1)
Ortho Esters and Related Compounds
956(1)
Miscellaneous Reactions
957(2)
ALCOHOLS AND PHENOLS 959(2)
GENERAL REFERENCES 961(236)
Resolution
963(2)
Alcohol Transposition
965(4)
Substitution
969(6)
Hydrogen Substitution
969(1)
Halide and Sulfonate Substitution
970(2)
Cyclic Sulfite and Thiocarbonate Substitution
972(1)
Nitrogen Substitution
973(1)
Acetate Substitution
974(1)
Oxidation
975(16)
Alkanes
975(2)
Arenes
977(1)
Alkenes
978(2)
Dienes
980(1)
Alkynes
981(1)
Alcohols
981(1)
Carbonyl Compounds
981(6)
Organometallics
987(4)
Alkene, Diene and Alkyne Additions
991(14)
Alkenes
991(12)
Dienes
1003(1)
Alkynes
1003(2)
Organoboranes
1005(8)
Hydroboration--Oxidation
1005(4)
Asymmetric Hydroboration
1008(1)
Carbonylation and Related Reactions
1009(1)
Other Reactions
1010(3)
Ether Cleavage
1013(60)
Cleavage of Acyclic Ethers
1013(6)
Reductions of Cyclic Ethers
1019(8)
Nucleophilic Opening of Cyclic Ethers
1027(18)
Alkylation of Cyclic Ethers
1045(18)
Epoxides
1045(16)
Oxetanes
1061(1)
Larger Rings
1061(2)
Various Rings
1063(1)
Rearrangement
1063(4)
Acetal Cleavage
1067(6)
Reduction
1073(52)
Peroxides
1073(2)
Aldehydes and Ketones
1075(39)
Hydrogenation
1075(1)
Reduction by Metals
1076(1)
Metal Hydride Reduction
1077(10)
Misecellaneous Reagents
1087(2)
Reduction of Aldehydes in Preference to Ketones
1089(1)
Reduction of Ketones in Preference to Aldehydes
1090(1)
Selective Reduction Between Aldehydes
1091(1)
Reduction of Conjugated Aldehydes in Preference to Nonconjugated Aldehydes
1091(1)
Reduction of Conjugated Aldehydes in Preference to Enones
1091(1)
Selective Reduction Between Ketones
1091(1)
Reduction of Enones in Preference to Aldehydes
1091(1)
Reduction of Enones in Preference to Ketones
1092(1)
Reduction of Ketones in Preference to Enones
1092(1)
Reduction of Enals and Enones to Allylic Alcohols
1092(4)
Reduction of Enals and Enones to Saturated Alcohols
1096(1)
Asymmetric Reduction of Aldehydes and Ketones
1097(14)
Pinacol Reaction
1111(3)
Carboxylic Acids and Derivatives
1114(11)
Alkylation of Carbonyl Compounds
1125(70)
Addition to Carbon Monoxide
1125(1)
Addition to Aldehydes and Ketones
1125(63)
Organometallic Additions
1125(51)
Miscellaneous Additions
1176(12)
Alkylation of α-Haloketones
1188(1)
Addition to Hemiacetals
1189(1)
Addition to Carboxylic Acids and Derivatives
1190(5)
Miscellaneous Reactions
1195(2)
ALDEHYDES AND KETONES 1197(2)
GENERAL REFERENCES 1199(422)
Carbonyl Transposition
1201(4)
Oxidation
1205(58)
Alkanes
1205(2)
AlKenes
1207(8)
Enamines
1215(1)
Alkenylphosphonates
1216(1)
Dienes and Polyenes
1216(1)
Alkynes
1217(5)
Halides, Nitrates and Sulfonates
1222(3)
Amines
1225(2)
Nitro Compounds
1227(2)
Diazo Compounds
1229(1)
Azides
1229(1)
Phosphorus Yields
1229(1)
Ethers
1230(3)
Sulfides
1233(1)
Sulfoxides
1233(1)
Sulfones
1234(1)
Phenols
1234(1)
Alcohols
1234(15)
Allylic Alcohols
1249(1)
Homoallylic Alcohols
1250(1)
Propargylic Alcohols
1250(1)
Diols and Derivatives
1250(6)
Halohydrins
1256(1)
α-Hydroxyketones
1256(1)
Hydroxyacids and Derivatives
1256(1)
Aldehydes
1257(1)
Ketones
1257(1)
Actals
1258(1)
Carboxylic Acids
1258(1)
Esters
1259(1)
Amides
1259(1)
Nitriles
1260(1)
Furans
1260(1)
Organometallics
1261(2)
Reduction of Phenols, Carboxylic Acids and Derivatives, and Nitriles
1263(12)
Phenols
1263(1)
Acylsilances
1263(1)
Carboxylic Acids
1263(2)
Acid Halides
1265(1)
Anhydrides
1266(1)
Esters
1267(1)
Thioesters
1268(1)
Selenoesters
1268(1)
Lactones
1268(1)
Amides and Imides
1269(2)
Nitriles
1271(2)
4,5-Dihydrooxazoles
1273(2)
Rearrangements
1275(38)
Isomerization
1275(2)
Epoxides
1277(3)
Vinylic Ethers
1280(1)
Pinacol and Related Rearrangements
1281(2)
Ring Rearrangement
1283(1)
Ring Opening
1284(1)
Ring Contraction
1285(2)
Ring Expansion
1287(15)
Electrocyclic Rearrangements
1302(9)
1,3-Claisen
1302(1)
3,3-Claisen
1302(1)
Amino-Claisen
1303(1)
Oxy-Claisen
1304(1)
Thio-Claisen
1304(1)
Claisen-Cope
1304(1)
Cope-Claisen
1305(1)
2,3-Wittig-Oxy-Cope
1305(1)
1,3-Oxy-Cope
1305(1)
3,3-Oxy-Cope
1306(1)
Oxy-Cope-Claisen
1307(1)
Oxy-Cope-Cope
1307(1)
Mannich-Aza-Coipe
1308(1)
Carroll
1308(1)
Nazarov
1308(1)
Electrocyclization
1309(1)
2,3-Sigmatropic Rearrangements
1309(1)
Fries Rearrangement
1310(1)
Miscellaneous Rearrangements
1311(2)
Condensation Reactions
1313(16)
Acetoacetic Ester
1313(1)
Acyloin
1313(2)
Benzoin and Related Reactions
1315(1)
Dieckmann and Related Reactions
1316(1)
Mannich
1317(1)
Michael
1317(1)
Thorpe-Ziegler
1317(1)
Aldol and Related Reactions
1317(10)
Metal Enolates
1318(7)
Related Reactions
1325(2)
Other Condensation Reactions
1327(2)
Cyclization and Annulation Reactions
1329(34)
Cyclization
1329(8)
Spiroannulation
1337(1)
One-Carbon Annulation
1338(1)
Two-Carbon Annulation
1338(7)
Three-Carbon Annulation
1345(11)
Four-Carbon Annulation
1356(6)
Robinson and Related Annulations
1356(2)
Reversed Robinson Annulation
1358(1)
Other Four-Carbon Annulations
1358(4)
Four-and Five-Carbon Annulation
1362(1)
Five-and Six-Carbon Annulation
1362(1)
Six-Carbon Annulation
1362(1)
Carbonylation and Related Reactions
1363(18)
Alkanes
1363(1)
Free Radicals
1363(1)
Organolithium Compounds
1364(1)
Organoboron Compounds
1365(2)
Organosilicon Compounds
1367(1)
Organotin Compounds
1367(1)
Organotitanium Compounds
1368(1)
Organozirconium Compounds
1368(1)
Organomolybedenum Compounds
1369(1)
Organotungsten Compounds
1369(1)
Organomanganese Compounds
1369(1)
Organoiron Compounds
1370(1)
Organoruthenium Compounds
1370(1)
Organocobalt Compounds
1371(1)
Organorhodium Compounds
1372(1)
Organonickel Compounds
1373(1)
Organopalladium Compounds
1374(3)
Organoplatinum Compounds
1377(1)
Organocopper Compounds
1377(1)
Organomercury Compounds
1378(1)
Organosamarium Compounds
1378(1)
Hydroformylation, Hydroacylation and Related Reactions
1378(3)
Electrophilic Acylation
1381(54)
Synthesis of Aldehydes
1381(2)
Synthesis of Ketones
1383(39)
From Carbonyl Cation Equivalents
1383(1)
From Acylium Salts
1384(1)
From Aldehydes
1384(2)
From Acylsilanes
1386(1)
From Carboxylic Acids
1386(3)
From Acid Halides
1389(11)
From Acid Anhydrides
1400(3)
From Esters and Lactones
1403(8)
From Thioesters
1411(1)
From Selenoesters
1411(1)
From Ortho Esters
1412(1)
From Ketenes
1412(1)
From Amides
1412(6)
From Thioamides
1418(1)
From Imides
1418(1)
From Acid Nitriles
1419(1)
From Nitriles
1420(2)
From Isocyanide Dichlorides
1422(1)
Friedel-Crafts and Related Reactions
1422(13)
Nucleophilic Acylation
1435(16)
Cyanohydrin Derivatives
1435(3)
Isonitriles
1438(1)
Iron Carbonyl Reagents
1439(1)
Allylic Amides
1440(1)
Allylic Ethers and Carbamates
1440(1)
Vinylic Ethers
1441(4)
Other Metallated Ethers
1445(1)
Amino Acetals
1446(1)
Miscellaneous Nucleophilic Acylation Reactions
1447(4)
Sulfur, Selenium and Tellurium Reagents
1451(10)
Sulfur Acetals
1451(4)
α-Thiosulfoxides
1455(1)
α-Substituted Sulfones
1456(1)
Thiocarbamates
1456(1)
Thioesters
1457(1)
Vinylic and Allylic Sulfides and Selenides
1457(1)
Miscellaneous Reactions
1458(3)
Heterocycles
1461(6)
Pyrylium Salts
1461(1)
1,3-Dioxanes
1461(1)
5,6-Dihydro-4H-1,3-oxazines
1462(1)
4,5-Dihydrooxazoles
1463(1)
4,5-Dihydroisoxazoles
1463(1)
4,5-Dihydro-1 H-imidazoles
1464(1)
Benzotriazoles
1464(1)
4,5-Dihydrothiazoles
1464(1)
Thiazoles
1465(1)
Benzothiazoles
1465(1)
1,3-Oxathiolane-3, 3-dioxides
1465(1)
1,3-Benzoxathiolium Salts
1465(2)
Carbonyl Homologation
1467(8)
Alkylation and Acylation of Aldehydes, Ketones and their Derivatives
1475(84)
Free Radical Alkylation
1475(1)
Direct Enol or Enolate Alkylation and Acylation
1476(7)
Enol Ethers
1483(1)
Enol Esters
1484(3)
Synthesis of Enol Esters
1484(1)
Applications
1485(2)
Enol Alanes
1487(1)
Enol Boranes
1488(1)
Enol Silanes
1488(18)
Preparation
1488(6)
Reactions
1494(12)
Enol Stannanes and Related Compounds
1506(1)
Enol Phosphorus Compounds
1507(1)
Enol Triflates
1507(1)
Enamines
1507(4)
Nitroalkenes
1511(2)
Imines
1513(3)
Hydrazones
1516(3)
Oxime Ethers
1519(1)
Oximes
1519(1)
Blocking Groups
1520(1)
Alkylation and Acylation of Carbonyl Dianions
1520(1)
Alkylation and Acylation of β-Ketoaldehydes
1521(1)
Alkylation and Acylation of β-Diketones
1522(6)
Alkylation and Acylation of β-Polyketones
1528(1)
Synthesis of β-Keto Acids, Esters, Amides, Imides and Nitriles and Decarboxylation
1528(18)
Alkylation of Enones
1546(13)
Alkylation of &alpha-and β-Substituted Carbonyl Compounds
1559(8)
Alkylation of Cyclopropyl Ketones
1559(1)
Reduction and Alkylation of α-Substituted Ketones
1560(2)
Substitutive Alkylation of α-Halocarbonyl Compounds
1562(2)
Free Radical Reactions
1562(1)
Electrophilic Substitution
1562(1)
Organolithium and -magnesium Compounds
1562(1)
Organoboron Compounds
1563(1)
Tin Reagents
1563(1)
Organocopper Compounds
1564(1)
Substitutive Alkylation of β-Halocarbonyl Compounds
1564(1)
Substitutive Alkylation of α-Diazocarbonyl Compounds
1565(1)
Decarboxylation--Allylation of β-Keto Acids and Esters
1566(1)
1,4-Addition to α,β-Unsaturated Carbonyl Compounds and Derivatives
1567(50)
Free Radical and Related Addition Reactions
1567(4)
Michael and Michael-like Addition Reactions
1571(17)
Organoboron Compounds
1588(1)
Organoaluminum -gallium and -thallium Compounds
1589(2)
Organosilicon Compounds
1591(2)
Organogermanium Compounds
1593(1)
Organotin Compounds
1593(1)
Organolead Compounds
1594(1)
Organostibine Compounds
1594(1)
Titanium Reagents
1594(1)
Organozirconium Compounds
1595(1)
Organomanganese Compounds
1595(1)
Organoiron Compounds
1595(1)
Organocobalt Compounds
1596(1)
Organorhodium Compounds
1596(1)
Organonickel Compounds
1596(2)
Organopalladium Compounds
1598(1)
Organocopper Compounds
1599(14)
Organosilver Compounds
1613(1)
Organozinc Compounds
1614(1)
Organomercury Compounds
1615(1)
Other Reagents
1616(1)
Miscellaneous Reactions
1617(4)
NITRILES, CARBOXYLIC ACIDS AND DERIVATIVES 1621(2)
GENERAL REFERENCES 1623(374)
Oxidation, Substitution and Addition
1625(52)
Alkanes
1625(2)
Arenes
1627(1)
Alkenes
1628(6)
Dienes
1634(2)
Alkynes
1636(3)
Allkyl Halides
1639(1)
Amines
1640(1)
Imines
1641(1)
Nitro Compounds
1641(1)
Nitrothioalkenes
1641(1)
Ethers
1641(5)
Sulfides
1646(1)
Alcohols
1646(4)
Diols
1650(2)
Aminoalcohols
1652(1)
Phenols
1653(1)
Aldehydes and Derivatives
1653(8)
Ketones
1661(9)
Hemiacetals and Lactols
1670(1)
Acetals
1670(2)
Carboxylic Acids
1672(1)
Esters
1673(1)
Amides
1674(1)
Nitriles
1675(2)
Reduction
1677(4)
Carbonylation, Carboxylation and Related Reactions
1681(30)
Carboxylic Acids
1681(9)
Acid Halides
1690(1)
Esters
1690(10)
Lactones
1700(1)
Acid Anhydrides
1700(1)
Amides
1700(4)
Lactams
1704(1)
Imides
1704(1)
Nitriles
1705(6)
Carboynl Homologation and Degradation
1711(6)
Homologation
1711(5)
Degradation
1716(1)
Alkylation, Acylation and Substitution of Nitriles, Carboxylic Acids and Derivatives
1717(92)
Carboxylic Acids
1717(7)
Esters
1724(53)
Anhydrides
1777(1)
Amides and Carbamates
1778(14)
Imides and Related Derivatives
1792(9)
Nitriles
1801(8)
Conjugate Addition To α,β-Unsaturated Nitriles, Carboxylic Acids and Derivatives
1809(34)
Rearrangements
1843(18)
Willgerodt and Related Reactions
1843(2)
Baeyer-Villager
1845(1)
Beckmann and Related Reactions
1845(1)
Schmidt
1846(1)
Curtius
1847(1)
Oxaziridine --- Amide
1847(1)
Favorski and Related Reactions
1847(2)
Benzilic Acid
1849(1)
Arndt-Eistert and Wolff
1850(1)
Cope
1851(1)
Aza-Cope
1851(1)
Claisen
1851(4)
Aza-Claisen and Related Rearrangements
1855(2)
Allylic Selendies
1857(1)
Imidate Esters
1857(1)
2,3-Sigmatropic Rearrangement
1858(1)
Ene Reaction--Oxidation
1859(1)
Ring Opening
1859(1)
Ring Expansion
1859(1)
Decarboxylation--Allylation
1860(1)
Other Reactions
1860(1)
Lactone and Lactam Formation
1861(68)
Interconversion of Nitriles, Carboxylic Acids and Derivatives
1929(66)
Carboxylic Acids to Acid halides
1929(1)
Carboxylic Acids to Acid Anhydrides
1930(2)
Carboxylic Acids to Esters
1932(9)
Carboxylic Acids to Amides
1941(8)
Carboxylic Acids to Imides
1949(1)
Carboxylic Acids to Nitriles
1949(1)
Acid Halides to Other Acid Halides
1950(1)
Acid Halides to Acid Anhydrides
1951(1)
Acid Halides to Esters
1952(1)
Acid Halides to Amides
1953(1)
Acid Halides to Imides
1954(1)
Acid Halides to Nitriles
1955(1)
Acid Anhydrides to Acid Halides
1955(1)
Acid Anhydrides to Esters
1955(2)
Acid Anhydrides to Amides
1957(1)
Acid Anhydrides to Imides
1958(1)
Esters to Carboxylic Acids
1959(9)
Esters to Acid Halides
1968(1)
Esters to Acid Anhydrides
1968(1)
Esters to Other Esters
1969(4)
Esters to Amides
1973(3)
Esters to Nitriles
1976(1)
Amides to Carboxylic Acids
1976(1)
Amides to Esters
1977(1)
Amides to Other Amides
1978(4)
Amides to Imides
1982(1)
Amides to Nitriles
1983(2)
Imides to Esters of Lactones
1985(1)
Imides to Amides
1985(1)
Imides to Other Imides
1986(1)
Nitriles to Carboxylic Acids
1986(1)
Nitriles to Esters
1987(1)
Nitriles to Amides
1988(2)
Other Interconversions
1990(5)
Miscellaneous Reactions
1995(2)
Transformation Index 1997

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