PROSE Award Finalist 2019 - Multivolume Reference/Science
Association of American Publishers Award for Professional and Scholarly Excellence
This 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.
- Covers and cross references so practicing chemists can easily navigate through the book’s comprehensive coverage of reagents and reactions
- Updates and expands a best-selling guide through the year 2011
"...the book is undoubtedly still of great value and every chemist working in the area of synthesis should have it within reach in the laboratory."
- Angewandte Chemie review of the 2nd edition
"...an indispensable reference work for designing and carrying out modern organic chemical synthesis.... It is amazing that so much information is contained in a single volume that is arranged in a logical and easy to use fashion."
- Analytical Biochemistry review of the 2nd edition
Table of Contents
Literature Abbreviations xxxix
Chemical Abbreviations xlix
Alkanes and Arenes 1
General References 3
1. Reduction 5
2. Coupling Reactions 193
3. Friedel-Crafts and Related Alkylation Reactions 343
4. Ring-Forming Reactions 355
5. Aromatization 467
Alkenes 519
General References 521
1. Isomerization of Alkenes 523
2. Elimination 571
3. Alkylidenation of Carbonyl and Related Compounds 645
4. Wittig and Related Reactions 661
5. Metal-Promoted Coupling Reactions 693
6. Arene, Alkyne, and Diene Addition Reactions 767
7. Dienes and Polyenes 879
8. Diels–Alder Reactions 1017
9. Cyclization, Annulation, and Related Reactions 1105
Alkynes 1143
General References 1145
1. Isomerization and Metathesis 1147
2. Elimination Reactions 1151
3. Wittig and Related Approaches 1169
4. Alkylation, Alkenylation, and Arylation of Alkynes and Allenes 1175
Halides 1231
General References 1233
1. Halogenation of Hydrocarbons 1237
3. Halogenation of Alkenes and Dienes 1269
4. Halogenation of Alkynes 1313
5. Interconversion of Halides 1333
6. Halogenation of Nitrogen Compounds 1345
7. Halogenation of Ethers 1355
8. Halogenation of Alcohols 1361
9. Halogenation of Phenols 1385
10. Halogenation of Sulfur and Selenium Compounds 1387
11. Halogenation of Carbonyl and Related Compounds 1397
12. Halodecarboxylation and Decarbonylation of Acids and Derivatives 1459
13. Halogenation of Organometallics 1467
Amines 1479
General References 1481
1. From Alkanes 1483
2. From Arenes 1487
3. From Alkenes, Dienes, and Alkynes 1491
4. From Alkyl and Aryl Halides Or Sulfonates 1529
5. From Other Amines and Derivatives 1545
6. From Azides 1595
7. From Nitro Compounds 1605
8. Heteroatom and Metal Substitution 1617
9. From Ethers, Alcohols, and Derivatives 1621
10. From Aldehydes, Ketones, and Derivatives 1631
11. From Carboxylic Acids and Derivatives 1697
12. From Nitriles 1709
13. From Isonitriles and Azo Compounds 1715
Ethers 1717
General References 1719
1. From Other Ethers 1721
2. Alkylation of Alcohols, Phenols, and Derivatives 1743
3. Alkane, Arene, Alkene, and Alkyne Substitutions and Additions 1859
4. Acetal, Carbonyl, and Ortho Ester Conversions 1963
5. Miscellaneous Reactions 2053
Alcohols and Phenols 2057
General References 2059
1. Resolution 2061
2. Alcohol Transposition 2067
3. Substitution 2071
4. Oxidation 2083
5. Alkene, Diene, and Alkyne Additions 2107
6. Organoboranes 2143
7. Ether Cleavage 2163
8. Reduction 2269
9. Alkylation of Carbonyl Compounds 2339
10. Miscellaneous Reactions 2437
Aldehydes and Ketones 2439
General References 2441
1. Carbonyl Transposition 2443
2. Oxidation 2449
3. Reduction of Phenols, Carboxylic Acids and Derivatives, and Nitriles 2587
4. Rearrangements 2605
5. Condensation Reactions 2687
6. Cyclization and Annulation Reactions 2721
7. Carbonylation and Related Reactions 2783
8. Electrophilic Acylation 2831
9. Nucleophilic Acylation 2927
10. Sulfur, Selenium, and Tellurium Reagents 2949
11. Heterocycles 2961
12. Carbonyl Homologation 2969
13. Alkylation and Acylation of Aldehydes, Ketones,And Their Derivatives 2981
15. 1,4-Addition To Α,Β-Unsaturated Carbonyl Compounds and Derivatives 3141
Nitriles, Carboxylic Acids, and Derivatives 3243
General References 3245
1. Oxidation, Substitution, and Addition 3247
2. Reduction 3331
3. Carbonylation, Carboxylation, and Related Reactions 3335
4. Carbonyl Homologation and Degradation 3399
5. Alkylation, Acylation, and Substitution of Nitriles, Carboxylic Acids, and Derivatives 3409
6. Conjugate Addition To Α,Β-Unsaturated Nitriles, Carboxylic Acids, and Derivatives 3549
7. Rearrangements 3619
8. Lactone and Lactam Formation 3647
9. Interconversion of Nitriles, Carboxylic Acids, and Derivatives 3749
10. Miscellaneous Reactions 3831
