| Comprehensive Organic Synthesis - Selectivity, Strategy and Efficiency in Modern Organic Chemistry, Volumes 1 - 9 |
Edited by: Trost, Barry M.; Fleming, Ian © 1991
Elsevier
Description: This set will be an essential reference work for all those seeking information on the solution of synthetic problems, whether they be experienced practitioners or chemists whose major interests lie outside organic synthesis.
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Volume 1. Additions to C—X π-Bonds, Part 1
Preface
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Contents of All Volumes
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Section 1. Nonstabilized Carbanion Equivalents
1.1 Carbanions of Alkali and Alkaline Earth Cations: (i) Synthesis and Structural Characterization
1.2 Carbanions of Alkali and Alkaline Earth Cations: (ii) Selectivity of Carbonyl Addition Reactions
1.3 Organoaluminum Reagents
1.4 Organocopper Reagents
1.5 Organotitanium and Organozirconium Reagents
1.6 Organochromium Reagents
1.7 Organozinc, Organocadmium and Organomercury Reagents
1.8 Organocerium Reagents
1.9 Samarium and Ytterbium Reagents
1.10 Lewis Acid Carbonyl Complexation
1.11 Lewis Acid Promoted Addition Reactions of Organometallic Compounds
1.12 Nucleophilic Addition to Imines and Imine Derivatives
1.13 Nucleophilic Addition to Carboxylic Acid Derivatives
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Section 2. Heteroatom-Stabilized Carbanion Equivalents
2.1 Nitrogen Stabilization
2.2 Boron Stabilization
2.3 Sulfur Stabilization
2.4 The Benzoin and Related Acyl Anion Equivalent Reactions
2.5 Silicon Stabilization
2.6 Selenium Stabilization
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Section 3. Transformation of the Carbonyl Group into Nonhydroxylic Groups
3.1 Alkene Synthesis
3.2 Epoxidation and Related Processes
3.3 Skeletal Reorganizations: Chain Extension and Ring Expansion
Author Index
Subject Index
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Volume 2. Additions to C—X π-Bonds, Part 2
Preface
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Contents of All Volumes
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Section 1. Uncatalyzed Additions of Nucleophilic Alkenes to C=X
1.1 Allyl Organometallics
1.2 Heteroatom-Stabilized Allylic Anions
1.3 Propargyl and Allenyl Organometallics
1.4 Formation of Enolates
1.5 The Aldol Reaction: Acid and General Base Catalysis
1.6 The Aldol Reaction: Group I and Group II Enolates
1.7 The Aldol Reaction: Group III Enolates
1.8 Zinc Enolates: The Reformatsky and Blaise Reactions
1.9 The Aldol Reaction: Transition Metal Enolates
1.10 The Henry (Nitroaldol) Reaction
1.11 The Knoevenagel Reaction
1.12 The Perkin Reaction
1.13 Darzens Glycidic Ester Condensation
1.14 Metal Homoenolates
1.15 Use of Enzymatic Aldol Reactions in Synthesis
1.16 Metalloenamines
1.17 Hydrazone Anions
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Section 2. Catalyzed Additions of Nucleophilic Alkenes to C=X
2.1 The Prins and Carbonyl Ene Reactions
2.2 Allylsilanes, Allylstannanes and Related Systems
2.3 Formation and Addition Reactions of Enol Ethers
2.4 Asymmetric Synthesis with Enol Ethers
2.5 Reactions of Activated Dienes with Aldehydes
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Section 3. Addition-Elimination Reactions (Acylations)
3.1 The Aliphatic Friedel-Crafts Reaction
3.2 The Bimolecular Aromatic Friedel-Crafts Reaction
3.3 The Intramolecular Aromatic Friedel-Crafts Reaction
3.4 The Reimer-Tiemann Reaction
3.5 The Vilsmeier-Haack Reaction
3.6 Acylation of Esters, Ketones and Nitriles
3.7 The Eschenmoser Coupling Reaction
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Section 4. Additions of Nucleophilic Alkenes to C=NR and C=NR2+
4.1 The Bimolecular Aliphatic Mannich and Related Reactions
4.2 The Bimolecular Aromatic Mannich React Ion
4.3 Reactions of Allyl and Propargyl/Allenic Organometallics with Imines and Iminium Ions
4.4 The Intramolecular Mannich and Related Reactions
4.5 Additions to
N-Acyliminium Ions
4.6 The Passerini and Ugi Reactions
Author Index
Subject Index
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Volume 3. Carbon-Carbon σ-Bond Formation
Preface
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Contents of All Volumes
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Section 1. Alkylation of Carbon
1.1 Alkylations of Enols and Enolates
1.2 Alkylations of Nitrogen-Stabilized Carbanions
1.3 Alkylations of Sulfur- and Selenium-Containing Carbanions
1.4 Alkylations of Other Heteroatom-Stabilized Carbanions
1.5 Alkylations of Nonstabilized Carbanions
1.6 Alkylations of Vinyl Carbanions
1.7 Alkylations of Alkynyl Carbanions
1.8 Friedel-Crafts Alkylations
1.9 Polyene Cyclizations
1.10 Transannular Electrophilic Cyclizations
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Section 2. Coupling Reactions
2.1 Coupling Reactions between
sp3 Carbon Centers
2.2 Coupling Reactions between
sp3 and
sp2 Carbon Centers
2.3 Coupling Reactions between
sp2 Carbon Centers
2.4 Coupling Reactions between
sp2 and
sp Carbon Centers
2.5 Coupling Reactions between
sp Carbon Centers
2.6 Pinacol Coupling Reactions
2.7 Acyloin Coupling Reactions
2.8 Kolbe Reactions
2.9 Oxidative Coupling of Phenols and Phenol Ethers
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Section 3. Rearrangement Reactions
3.1 Wagner-Meerwein Rearrangements
3.2 The Pinacol Rearrangement
3.3 Acid-Catalyzed Rearrangements of Epoxides
3.4 The Semipinacol and Other Rearrangements
3.5 Dienone-Phenol Rearrangements and Related Reactions
3.6 Benzil-Benzilic Acid Rearrangements
3.7 The Favorskii Rearrangement
3.8 The Ramberg-Bäcklund Rearrangement
3.9 The Wolff Rearrangement
3.10 The Stevens and Related Rearrangements
3.11 The Wittig Rearrangement
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Section 4. Other Carbon-Carbon Bond Forming Reactions
4.1 Carbonylation and Decarbonylation Reactions
4.2 Carbon-Carbon Bond Formation by C—H Insertion
Author Index
Subject Index
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Volume 4. Additions to and Substitutions at C—C π-Bonds
Preface
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Contents of All Volumes
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Section 1. Polar Additions to Activated Alkenes and Alkynes
1.1 Stabilized Nucleophiles with Electron Deficient Alkenes and Alkynes
1.2 Conjugate Additions of Reactive Carbanions to Activated Alkenes and Alkynes
1.3 Conjugate Additions of Carbon Ligands to Activated Alkenes and Alkynes Mediated by Lewis Acids
1.4 Organocuprates in the Conjugate Addition Reaction
1.5 Asymmetric Nucleophilic Addition to Electron Deficient Alkenes
1.6 Nucleophilic Addition-Electrophilic Coupling with a Carbanion Intermediate
1.7 Addition of H—X Reagents to Alkenes and Alkynes
1.8 Electrophilic Addition of X—Y Reagents to Alkenes and Alkynes
1.9 Electrophilic Heteroatom Cyclizations
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Section 2. Nucleophilic Aromatic Substitutions
2.1 Arene Substitution
via Nucleophilic Addition to Electron Deficient Arenes
2.2 Nucleophilic Coupling with Aryl Radicals
2.3 Nucleophilic Coupling with Arynes
2.4 Nucleophilic Addition to Arene-Metal Complexes
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Section 3. Polar Additions to Alkenes and Alkynes
3.1 Heteroatom Nucleophiles with Metal-Activated Alkenes and Alkynes
3.2 Carbon Nucleophiles with Alkenes and Alkynes
3.3 Nucleophiles with Allyl-Metal Complexes
3.4 Nucleophiles with Cationic Pentadienyl-Metal Complexes
3.5 Carbon Electrophiles with Dienes and Polyenes Promoted by Transition Metals
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Section 4. Nonpolar Additions to Alkenes and Alkynes
4.1 Radical Addition Reactions
4.2 Radical Cyclizations and Sequential Radical Reactions
4.3 Vinyl Substitutions with Organopalladium Intermediates
4.4 Carbometallation of Alkenes and Alkynes
4.5 Hydroformylation and Related Additions of Carbon Monoxide to Alkenes and Alkynes
4.6 Methylene and Nonfunctionalized Alkylidene Transfer to Form Cyclopropanes
4.7 Formation and Further Transformations of 1,1-Dihalocyclopropanes
4.8 Addition of Ketocarbenes to Alkynes, Alkynes and Aromatic Systems
4.9 Intermolecular 1,3-Dipolar Cycloadditions
4.10 Intramolecular 1,3-Dipolar Cycloadditions
Author Index
Subject Index
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Volume 5. Combining C—C π-Bonds
Preface
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Contents of All Volumes
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Section 1. Ene Reactions
1.1 Ene Reactions with Alkenes as Enophiles
1.2 Metallo-Ene Reactions
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Section 2. [2 + 2] Cycloadditions
2.1 Thermal Cyclobutane Ring Formation
2.2 Formation of Four-Membered Heterocycles
2.3 Photochemical Cycloadditions
2.4 The Paterno-Büchi Reaction
2.5 Di-π-Methane Photoisomerizations
2.6 Oxa-Di-π-Methane Photoisomerizations
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Section 3. [3 + 2] Cycloadditions
3.1 Thermal Cycloadditions
3.2 Transition Metal Mediated Cycloadditions
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Section 4. [4 + 2] Cycloadditions
4.1 Intermolecular Diels-Alder Reactions
4.2 Heterodienophile Additions to Dienes
4.3 Heterodiene Additions
4.4 Intramolecular Diels-Alder Reactions
4.5 Retrograde Diels-Alder Reactions
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Section 5. Higher-Order Cycloadditions
5.1 [4 + 3] Cycloadditions
5.2 [4 + 4] and [6 + 4] Cycloadditions
5.3 [3 + 2] and [5 + 2] Arene-Alkene Photocycloadditions
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Section 6. Electrocyclic Processes
6.1 Cyclobutene Ring Opening Reactions
6.2 1,3-Cyclohexadiene Formation Reactions
6.3 Nazarov and Related Cationic Cyclizations
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Section 7. Sigmatropic Processes
7.1 Cope, Oxy-Cope and Anionic Oxy-Cope Rearrangements
7.2 Claisen Rearrangements
7.3 Consecutive Rearrangements
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Section 8. Small Ring Rearrangements
8.1 Rearrangements of Vinylcyclopropanes and Related Systems
8.2 Rearrangements of Divinylcyclopropanes
8.3 Charge-Accelerated Rearrangements
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Section 9. Other Transition Metal Associated Reactions
9.1 The Pauson-Khand Reaction
9.2 Metal-Carbene Cycloadditions
9.3 Alkene Metathesis and Related Reactions
9.4 [2 + 2 + 2] Cycloadditions
9.5 Zirconium-Promoted Bicyclization of Enynes
9.6 Metal-Catalyzed Cycloaddition of Small Ring Compounds
Author Index
Subject Index
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Volume 6. Heteroatom Manipulation
Preface
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Contents of All Volumes
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Section 1. Displacement by Substitution Processes
1.1 Synthesis of Alcohols and Ethers
1.2 Synthesis of Glycosides
1.3 Synthesis of Amines and Ammonium Salts
1.4 Synthesis of Nitroso, Nitro and Related Compounds
1.5 Synthesis of Sulfides, Sulfoxides and Sulfones
1.6 Synthesis of Phosphonium Ylides
1.7 Synthesis of Halides
1.8 Synthesis of Pseudohalides, Nitriles and Related Compounds
1.9 Ritter-Type Reactions
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Section 2. Acylation-Type Reactions
2.1 Synthesis of Acid Halides, Anhydrides and Related Compounds
2.2 Synthesis of Esters, Activated Esters and Lactones
2.3 Synthesis of Amides and Related Compounds
2.4 Synthesis of Thioamides and Thiolactams
2.5 Synthesis of Thioesters and Thiolactones
2.6 Selenoesters of All Oxidation States
2.7 Synthesis of Iminium Salts, Orthoesters and Related Compounds
2.8 Inorganic Acid Derivatives
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Section 3. Protecting Groups
3.1 Protecting Groups
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Section 4. Functional Group Interconversion
4.1 Carbonyl Group Derivatization
4.2 Use of Carbonyl Derivatives for Heterocyclic Synthesis
4.3 Functional Group Transformations
via Carbonyl Derivatives
4.4 Degradation Reactions
4.5 Functional Group Transformations
via Allyl Rearrangement
4.6 2,3-Sigmatropic Rearrangements
4.7 Polonovski- and Pummerer-Type Reactions and the Nef Reaction
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Section 5. Elimination Reactions
5.1 Eliminations to Form Alkenes, Allenes and Alkynes and Related Reactions
5.2 Reductive Elimination, Vicinal Deoxygenation and Vicinal Desilylation
5.3 The Cope Elimination, Sulfoxide Elimination and Related Thermal Reactions
5.4 Fragmentation Reactions
Author Index
Subject Index
Preface
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Contents of All Volumes
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Section 1. Oxidation of Unactivated C—H Bonds
1.1 Oxidation by Chemical Methods
1.2 Oxidation by Nitrene Insertion
1.3 Oxidation by Remote Functionalization Methods
1.4 Oxidation by Microbial Methods
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Section 2. Oxidation of Activated C—H Bonds
2.1 Oxidation Adjacent to C=C Bonds
2.2 Oxidation Adjacent to C=X Bonds by Dehydrogenation
2.3 Oxidation Adjacent to C=X Bonds by Hydroxylation Methods
2.4 Oxidation Adjacent to Sulfur
2.5 Oxidation Adjacent to Nitrogen
2.6 Oxidation Adjacent to Oxygen of Ethers
2.7 Oxidation Adjacent to Oxygen of Alcohols by Chromium Reagents
2.8 Oxidation Adjacent to Oxygen of Alcohols by Activated DMSO Methods
2.9 Oxidation Adjacent to Oxygen of Alcohols by Other Methods
2.10 Vinylic and Arylic C—H Oxidation
2.11 Synthesis of Quinones
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Section 3. Oxidation of C=C Bonds
3.1 Addition Reactions with Formation of Carbon-Oxygen Bonds: (i) General Methods of Epoxidation
3.2 Addition Reactions with Formation of Carbon-Oxygen Bonds: (ii) Asymmetric Methods of Epoxidation
3.3 Addition Reactions with Formation of Carbon-Oxygen Bonds: (iii) Glycol Forming Reactions
3.4 Addition Reactions with Formation of Carbon-Oxygen Bonds: (iv) The Wacker Oxidation and Related Reactions
3.5 Addition Reactions with Formation of Carbon-Nitrogen Bonds
3.6 Addition Reactions with Formation of Carbon-Sulfur or Carbon-Selenium Bonds
3.7 Addition Reactions with Formation of Carbon-Halogen Bonds
3.8 Cleavage Reactions
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Section 4. Oxidation of C—X Bonds
4.1 Oxidation of Carbon-Boron Bonds
4.2 Oxidation of Carbon-Metal Bonds
4.3 Oxidation of Carbon-Silicon Bonds
4.4 Oxidation of Carbon-Halogen Bonds
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Section 5. Oxidation of C—C Bonds
5.1 The Baeyer-Villiger Reaction
5.2 The Beckmann and Related Reactions
5.3 Glycol Cleavage Reactions
5.4 The Hunsdiecker and Related Reactions
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Section 6. Oxidation of Heteroatoms
6.1 Oxidation of Nitrogen and Phosphorus
6.2 Oxidation of Sulfur, Selenium and Tellurium
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Section 7. Special Topics
7.1 Oxidation by Electrochemical Methods
7.2 Oxidative Rearrangement Reactions
7.3 Solid-Supported Oxidants
7.4 Electron-Transfer Oxidation
Author Index
Subject Index
Preface
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Contents of All Volumes
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Section 1. Reduction of C=X Bonds
1.1 Reduction of C=O to CHOH by Metal Hydrides
1.2 Reduction of C=N to CHNH by Metal Hydrides
1.3 Reduction of C=X to CHXH by Hydride Delivery from Carbon
1.4 Reduction of C=X to CHXH by Dissolving Metals and Related Methods
1.5 Reduction of C=X to CHXH Electrolytically
1.6 Reduction of C=X to CHXH by Catalytic Hydrogenation
1.7 Reduction of C=X to CHXH by Chirally Modified Hydride Reagents
1.8 Reduction of C=X to CHXH Using Enzymes and Microorganisms
1.9 Reduction of Acetals, Azaacetals and Thioacetals to Ethers
1.10 Reduction of Carboxylic Acid Derivatives to Alcohols, Ethers and Amines
1.11 Reduction of Carboxylic Acids to Aldehydes by Metal Hydrides
1.12 Reduction of Carboxylic Acids to Aldehydes by Other Methods
1.13 Reduction of C=X to CH
2 by Dissolving Metals and Related Methods
1.14 Reduction of C=X to CH
2 by Wolff-Kishner and Other Hydrazone Methods
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Section 2. Reduction of X=Y Bonds
2.1 Reduction of Nitro and Nitroso Compounds
2.2 Reduction of N=N, N—N, N—O and O—O Bonds
2.3 Reduction of S=O and SO
2 to S, P=O to P, and of S—X to S—H
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Section 3. Reduction of C=C and C≡C Bonds
3.1 Heterogeneous Catalytic Hydrogenation of C=C and C≡C
3.2 Homogeneous Catalytic Hydrogenation of C=C and C≡C
3.3 Reductions of C=C and C≡C by Noncatalytic Chemical Methods
3.4 Partial Reduction of Aromatic Rings by Dissolving Metals and by Other Methods
3.5 Partial Reduction of Enones, Styrenes and Related Systems
3.6 Partial and Complete Reduction of Pyridines and Their Benzo Analogs
3.7 Partial and Complete Reduction of Pyrroles, Furans, Thiophenes and Their Benzo Analogs
3.8 Partial and Complete Reduction of Heterocycles Containing More Than One Heteroatom
3.9 Hydrozirconation of C=C and C≡C and Hydrometallation by Other Metals
3.10 Hydroboration of C=C and C≡C
3.11 Hydroalumination of C=C and C≡C
3.12 Hydrosilylation of C=C and C≡C
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Section 4. Reduction of C—X to C—H
4.1 Reduction of Saturated Alkyl Halides to Alkanes
4.2 Reduction of Saturated Alcohols and Amines to Alkanes
4.3 Reduction of Sulfur-Carbon Bonds and of Other Heteroatoms Bonded to Tetrahedral Carbon
4.4 Reduction of Epoxides
4.5 Reduction of Vinyl Halides to Alkenes, and of Aryl Halides and Related Compounds to Arenes
4.6 Reduction of Ketones to Alkenes
4.7 Hydrogenolysis of Allyl and Benzyl Halides and Related Compounds
4.8 Reduction of α-Substituted Carbonyl Compounds—CX—CO—to Carbonyl Compounds—CH—CO—
Author Index
Subject Index
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Volume 9. Cumulative Indexes
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Contents of All Volumes
Cumulative Author Index
Cumulative Subject Index
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