What is included with this book?
Alkylation of Nucleophilic Carbon Intermediates | p. 1 |
Generation of Carbanions by Deprotonation | p. 1 |
Regioselectivity and Stereoselectivity in Enolate Formation | p. 5 |
Other Means of Generating Enolates | p. 10 |
Alkylation of Enolates | p. 11 |
Generation and Alkylation of Dianions | p. 20 |
Medium Effects in the Alkylation of Enolates | p. 20 |
Oxygen versus Carbon as the Site of Alkylation | p. 23 |
Alkylation of Aldehydes, Esters, Amides, and Nitriles | p. 28 |
The Nitrogen Analogs of Enols and Enolates--Enamines and Imine Anions | p. 31 |
Alkylation of Carbon Nucleophiles by Conjugate Addition | p. 39 |
General References | p. 47 |
Problems | p. 47 |
Reaction of Carbon Nucleophiles with Carbonyl Groups | p. 57 |
Aldol Addition and Condensation Reactions | p. 57 |
The General Mechanism | p. 57 |
Mixed Aldol Condensations with Aromatic Aldehydes | p. 60 |
Control of Regiochemistry and Stereochemistry of Mixed Aldol Reactions of Aliphatic Aldehydes and Ketones | p. 62 |
Intramolecular Aldol Reactions and the Robinson Annulation | p. 89 |
Addition Reactions of Imines and Iminium Ions | p. 96 |
The Mannich Reaction | p. 96 |
Amine-Catalyzed Condensation Reactions | p. 100 |
Acylation of Carbanions | p. 101 |
The Wittig and Related Reactions of Phosphorus-Stabilized Carbon Nucleophiles | p. 111 |
Reactions of Carbonyl Compounds with [alpha]-Trimethylsilylcarbanions | p. 120 |
Sulfur Ylides and Related Nucleophiles | p. 122 |
Nucleophilic Addition--Cyclization | p. 127 |
General References | p. 128 |
Problems | p. 128 |
Functional Group Interconversion by Nucleophilic Substitution | p. 141 |
Conversion of Alcohols to Alkylating Agents | p. 141 |
Sulfonate Esters | p. 141 |
Halides | p. 142 |
Introduction of Functional Groups by Nucleophilic Substitution at Saturated Carbon | p. 147 |
General Solvent Effects | p. 147 |
Nitriles | p. 150 |
Azides | p. 150 |
Oxygen Nucleophiles | p. 152 |
Nitrogen Nucleophiles | p. 155 |
Sulfur Nucleophiles | p. 158 |
Phosphorus Nucleophiles | p. 158 |
Summary of Nucleophilic Substitution at Saturated Carbon | p. 159 |
Nucleophilic Cleavage of Carbon-Oxygen Bonds in Ethers and Esters | p. 159 |
Interconversion of Carboxylic Acid Derivatives | p. 164 |
Preparation of Reactive Reagents for Acylation | p. 166 |
Preparation of Esters | p. 172 |
Preparation of Amides | p. 172 |
Problems | p. 180 |
Electrophilic Additions to Carbon--Carbon Multiple Bonds | p. 191 |
Addition of Hydrogen Halides | p. 191 |
Hydration and Other Acid-Catalyzed Additions of Oxygen Nucleophiles | p. 195 |
Oxymercuration | p. 196 |
Addition of Halogens to Alkenes | p. 200 |
Electrophilic Sulfur and Selenium Reagents | p. 209 |
Addition of Other Electrophilic Reagents | p. 216 |
Electrophilic Substitution Alpha to Carbonyl Groups | p. 216 |
Additions to Allenes and Alkynes | p. 222 |
Addition at Double Bonds via Organoborane Intermediates | p. 226 |
Hydroboration | p. 226 |
Reactions of Organoboranes | p. 232 |
Enantioselective Hydroboration | p. 236 |
Hydroboration of Alkynes | p. 239 |
General References | p. 240 |
Problems | p. 241 |
Reduction of Carbonyl and Other Functional Groups | p. 249 |
Addition of Hydrogen | p. 249 |
Catalytic Hydrogenation | p. 249 |
Other Hydrogen-Transfer Reagents | p. 262 |
Group III Hydride-Donor Reagents | p. 262 |
Reduction of Carbonyl Compounds | p. 262 |
Stereoselectivity of Hydride Reduction | p. 273 |
Reduction of Other Functional Groups by Hydride Donors | p. 280 |
Group IV Hydride Donors | p. 286 |
Hydrogen-Atom Donors | p. 288 |
Dissolving-Metal Reductions | p. 290 |
Addition of Hydrogen | p. 292 |
Reductive Removal of Functional Groups | p. 296 |
Reductive Carbon--Carbon Bond Formation | p. 299 |
Reductive Deoxygenation of Carbonyl Groups | p. 307 |
Reductive Elimination and Fragmentation | p. 310 |
General References | p. 315 |
Problems | p. 316 |
Cycloadditions, Unimolecular Rearrangements, and Thermal Eliminations | p. 331 |
Cycloaddition Reactions | p. 331 |
The Diels--Alder Reaction: General Features | p. 332 |
The Diels--Alder Reaction: Dienophiles | p. 339 |
The Diels--Alder Reaction: Dienes | p. 345 |
Asymmetric Diels--Alder Reactions | p. 349 |
Intramolecular Diels--Alder Reactions | p. 353 |
Dipolar Cycloaddition Reactions | p. 359 |
[2 + 2] Cycloadditions and Other Reactions Leading to Cyclobutanes | p. 367 |
Photochemical Cycloaddition Reactions | p. 370 |
[3,3] Sigmatropic Rearrangements | p. 376 |
Cope Rearrangements | p. 376 |
Claisen Rearrangements | p. 383 |
[2,3] Sigmatropic Rearrangements | p. 394 |
Ene Reactions | p. 399 |
Unimolecular Thermal Elimination Reactions | p. 403 |
Cheletropic Elimination | p. 403 |
Decomposition of Cyclic Azo Compounds | p. 405 |
[beta] Eliminations Involving Cyclic Transition States | p. 408 |
General References | p. 414 |
Problems | p. 414 |
Organometallic Compounds of the Group I, II, and III Metals | p. 433 |
Preparation and Properties | p. 433 |
Reactions of Organomagnesium and Organolithium Compounds | p. 445 |
Reactions with Alkylating Agents | p. 445 |
Reactions with Carbonyl Compounds | p. 446 |
Organic Derivatives of Group IIB and Group IIIB Metals | p. 458 |
Organozinc Compounds | p. 459 |
Organocadmium Compounds | p. 463 |
Organomercury Compounds | p. 464 |
Organoindium Reagents | p. 465 |
Organolanthanide Reagents | p. 467 |
General References | p. 468 |
Problems | p. 468 |
Reactions Involving the Transition Metals | p. 477 |
Organocopper Intermediates | p. 477 |
Preparation and Structure of Organocopper Reagents | p. 477 |
Reactions Involving Organocopper Reagents and Intermediates | p. 481 |
Reactions Involving Organopalladium Intermediates | p. 499 |
Palladium-Catalyzed Nucleophilic Substitution and Alkylation | p. 501 |
The Heck Reaction | p. 503 |
Palladium-Catalyzed Cross Coupling | p. 507 |
Carbonylation Reactions | p. 521 |
Reactions Involving Organonickel Compounds | p. 525 |
Reactions Involving Rhodium and Cobalt | p. 529 |
Organometallic Compounds with [pi] Bonding | p. 531 |
General References | p. 535 |
Problems | p. 536 |
Carbon--Carbon Bond-Forming Reactions of Compounds of Boron, Silicon, and Tin | p. 547 |
Organoboron Compounds | p. 547 |
Synthesis of Organoboranes | p. 547 |
Carbon--Carbon Bond-Forming Reactions of Organoboranes | p. 549 |
Organosilicon Compounds | p. 563 |
Synthesis of Organosilanes | p. 563 |
Carbon--Carbon Bond-Forming Reactions | p. 567 |
Organotin Compounds | p. 576 |
Synthesis of Organostannanes | p. 576 |
Carbon--Carbon Bond-Forming Reactions | p. 579 |
General References | p. 585 |
Problems | p. 586 |
Reactions Involving Carbocations, Carbenes, and Radicals as Reactive Intermediates | p. 595 |
Reactions Involving Carbocation Intermediates | p. 595 |
Carbon-Carbon Bond Formation Involving Carbocations | p. 596 |
Rearrangement of Carbocations | p. 602 |
Related Rearrangements | p. 609 |
Fragmentation Reactions | p. 612 |
Reactions Involving Carbenes and Nitrenes | p. 614 |
Structure and Reactivity of Carbenes | p. 617 |
Generation of Carbenes | p. 620 |
Addition Reactions | p. 625 |
Insertion Reactions | p. 634 |
Generation and Reactions of Ylides by Carbenoid Decomposition | p. 637 |
Rearrangement Reactions | p. 639 |
Related Reactions | p. 641 |
Nitrenes and Related Intermediates | p. 642 |
Rearrangements to Electron-Deficient Nitrogen | p. 646 |
Reactions Involving Free-Radical Intermediates | p. 651 |
Sources of Radical Intermediates | p. 652 |
Introduction of Functionality by Radical Reactions | p. 654 |
Addition Reactions of Radicals to Substituted Alkenes | p. 657 |
Cyclization of Free-Radical Intermediates | p. 660 |
Fragmentation and Rearrangement Reactions | p. 674 |
General References | p. 679 |
Problems | p. 680 |
Aromatic Substitution Reactions | p. 693 |
Electrophilic Aromatic Substitution | p. 693 |
Nitration | p. 693 |
Halogenation | p. 695 |
Friedel-Crafts Alkylations and Acylations | p. 699 |
Electrophilic Metalation | p. 711 |
Nucleophilic Aromatic Substitution | p. 714 |
Aryl Diazonium Ions as Synthetic Intermediates | p. 714 |
Substitution by the Addition-Elimination Mechanism | p. 722 |
Substitution by the Elimination-Addition Mechanism | p. 724 |
Transition-Metal-Catalyzed Substitution Reactions | p. 728 |
Aromatic Radical Substitution Reactions | p. 731 |
Substitution by the S[subscript RN]1 Mechanism | p. 734 |
General References | p. 736 |
Problems | p. 736 |
Oxidations | p. 747 |
Oxidation of Alcohols to Aldehydes, Ketones, or Carboxylic Acids | p. 747 |
Transition-Metal Oxidants | p. 747 |
Other Oxidants | p. 752 |
Addition of Oxygen at Carbon-Carbon Double Bonds | p. 757 |
Transition-Metal Oxidants | p. 757 |
Epoxides from Alkenes and Peroxidic Reagents | p. 767 |
Transformations of Epoxides | p. 772 |
Reaction of Alkenes with Singlet Oxygen | p. 782 |
Cleavage of Carbon-Carbon Double Bonds | p. 786 |
Transition-Metal Oxidants | p. 786 |
Oxonolysis | p. 788 |
Selective Oxidative Cleavages at Other Functional Groups | p. 790 |
Cleavage of Glycols | p. 790 |
Oxidative Decarboxylation | p. 792 |
Oxidation of Ketones and Aldehydes | p. 794 |
Transition-Metal Oxidants | p. 794 |
Oxidation of Ketones and Aldehydes by Oxygen and Peroxidic Compounds | p. 798 |
Oxidation with Other Reagents | p. 802 |
Allylic Oxidation | p. 803 |
Transition-Metal Oxidants | p. 803 |
Other Oxidants | p. 805 |
Oxidations at Unfunctionalized Carbon | p. 807 |
General References | p. 809 |
Problems | p. 809 |
Planning and Execution of Multistep Syntheses | p. 821 |
Protective Groups | p. 822 |
Hydroxyl-Protecting Groups | p. 822 |
Amino-Protecting Groups | p. 831 |
Carbonyl-Protecting Groups | p. 835 |
Carboxylic Acid-Protecting Groups | p. 837 |
Synthetic Equivalent Groups | p. 839 |
Synthetic Analysis and Planning | p. 845 |
Control of Stereochemistry | p. 846 |
Illustrative Syntheses | p. 848 |
Juvabione | p. 848 |
Longifolene | p. 859 |
Prelog-Djerassi Lactone | p. 869 |
Taxol | p. 881 |
Epothilone A | p. 890 |
Solid-Phase Synthesis | p. 897 |
Solid-Phase Synthesis of Polypeptides | p. 897 |
Solid-Phase Synthesis of Oligonucleotides | p. 900 |
Combinatorial Synthesis | p. 903 |
General References | p. 909 |
Problems | p. 910 |
References for Problems | p. 923 |
Index | p. 947 |
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