Reactions and synthesis

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Reactions and synthesis / Francis A. Carey and Richard J. Sundberg

版:

4th ed

資料種別:

図書

出版情報:

New York : Kluwer Academic/Plenum Publishers, c2001

形態:

xii, 965 p. ; 26 cm

シリーズ名:

Advanced organic chemistry / Francis A. Carey and Richard J. Sundberg ; pt. B <BA49002999>

著者名:

ISBN:

9780306462443 [0306462443] (: hard)
9780306462450 [0306462451] (: pbk)

書誌ID:

BA53082834

子書誌情報

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書誌詳細

注記:

Includes bibliographical references and index

主題:

Chemistry, Organic

言語:

英語

目次情報:

Alkylation of Nucleophilic Carbon Intermediates / Chapter 1.：

Generation of Carbanions by Deprotonation / 1.1.：

Regioselectivity and Stereoselectivity in Enolate Formation / 1.2.：

Other Means of Generating Enolates / 1.3.：

Alkylation of Enolates / 1.4.：

Generation and Alkylation of Dianions / 1.5.：

Medium Effects in the Alkylation of Enolates / 1.6.：

Oxygen versus Carbon as the Site of Alkylation / 1.7.：

Alkylation of Aldehydes, Esters, Amides, and Nitriles / 1.8.：

The Nitrogen Analogs of Enols and Enolates--Enamines and Imine Anions / 1.9.：

Alkylation of Carbon Nucleophiles by Conjugate Addition / 1.10.：

General References

Problems

Reaction of Carbon Nucleophiles with Carbonyl Groups / Chapter 2.：

Aldol Addition and Condensation Reactions / 2.1.：

The General Mechanism / 2.1.1.：

Mixed Aldol Condensations with Aromatic Aldehydes / 2.1.2.：

Control of Regiochemistry and Stereochemistry of Mixed Aldol Reactions of Aliphatic Aldehydes and Ketones / 2.1.3.：

Intramolecular Aldol Reactions and the Robinson Annulation / 2.1.4.：

Addition Reactions of Imines and Iminium Ions / 2.2.：

The Mannich Reaction / 2.2.1.：

Amine-Catalyzed Condensation Reactions / 2.2.2.：

Acylation of Carbanions / 2.3.：

The Wittig and Related Reactions of Phosphorus-Stabilized Carbon Nucleophiles / 2.4.：

Reactions of Carbonyl Compounds with [alpha]-Trimethylsilylcarbanions / 2.5.：

Sulfur Ylides and Related Nucleophiles / 2.6.：

Nucleophilic Addition--Cyclization / 2.7.：

Functional Group Interconversion by Nucleophilic Substitution / Chapter 3.：

Conversion of Alcohols to Alkylating Agents / 3.1.：

Sulfonate Esters / 3.1.1.：

Halides / 3.1.2.：

Introduction of Functional Groups by Nucleophilic Substitution at Saturated Carbon / 3.2.：

General Solvent Effects / 3.2.1.：

Nitriles / 3.2.2.：

Azides / 3.2.3.：

Oxygen Nucleophiles / 3.2.4.：

Nitrogen Nucleophiles / 3.2.5.：

Sulfur Nucleophiles / 3.2.6.：

Phosphorus Nucleophiles / 3.2.7.：

Summary of Nucleophilic Substitution at Saturated Carbon / 3.2.8.：

Nucleophilic Cleavage of Carbon-Oxygen Bonds in Ethers and Esters / 3.3.：

Interconversion of Carboxylic Acid Derivatives / 3.4.：

Preparation of Reactive Reagents for Acylation / 3.4.1.：

Preparation of Esters / 3.4.2.：

Preparation of Amides / 3.4.3.：

Electrophilic Additions to Carbon--Carbon Multiple Bonds / Chapter 4.：

Addition of Hydrogen Halides / 4.1.：

Hydration and Other Acid-Catalyzed Additions of Oxygen Nucleophiles / 4.2.：

Oxymercuration / 4.3.：

Addition of Halogens to Alkenes / 4.4.：

Electrophilic Sulfur and Selenium Reagents / 4.5.：

Addition of Other Electrophilic Reagents / 4.6.：

Electrophilic Substitution Alpha to Carbonyl Groups / 4.7.：

Additions to Allenes and Alkynes / 4.8.：

Addition at Double Bonds via Organoborane Intermediates / 4.9.：

Hydroboration / 4.9.1.：

Reactions of Organoboranes / 4.9.2.：

Enantioselective Hydroboration / 4.9.3.：

Hydroboration of Alkynes / 4.9.4.：

Reduction of Carbonyl and Other Functional Groups / Chapter 5.：

Addition of Hydrogen / 5.1.：

Catalytic Hydrogenation / 5.1.1.：

Other Hydrogen-Transfer Reagents / 5.1.2.：

Group III Hydride-Donor Reagents / 5.2.：

Reduction of Carbonyl Compounds / 5.2.1.：

Stereoselectivity of Hydride Reduction / 5.2.2.：

Reduction of Other Functional Groups by Hydride Donors / 5.2.3.：

Group IV Hydride Donors / 5.3.：

Hydrogen-Atom Donors / 5.4.：

Dissolving-Metal Reductions / 5.5.：

Reductive Removal of Functional Groups / 5.5.1.：

Reductive Carbon--Carbon Bond Formation / 5.5.3.：

Reductive Deoxygenation of Carbonyl Groups / 5.6.：

Reductive Elimination and Fragmentation / 5.7.：

Cycloadditions, Unimolecular Rearrangements, and Thermal Eliminations / Chapter 6.：

Cycloaddition Reactions / 6.1.：

The Diels--Alder Reaction: General Features / 6.1.1.：

The Diels--Alder Reaction: Dienophiles / 6.1.2.：

The Diels--Alder Reaction: Dienes / 6.1.3.：

Asymmetric Diels--Alder Reactions / 6.1.4.：

Intramolecular Diels--Alder Reactions / 6.1.5.：

Dipolar Cycloaddition Reactions / 6.2.：

[2 + 2] Cycloadditions and Other Reactions Leading to Cyclobutanes / 6.3.：

Photochemical Cycloaddition Reactions / 6.4.：

[3,3] Sigmatropic Rearrangements / 6.5.：

Cope Rearrangements / 6.5.1.：

Claisen Rearrangements / 6.5.2.：

[2,3] Sigmatropic Rearrangements / 6.6.：

Ene Reactions / 6.7.：

Unimolecular Thermal Elimination Reactions / 6.8.：

Cheletropic Elimination / 6.8.1.：

Decomposition of Cyclic Azo Compounds / 6.8.2.：

[beta] Eliminations Involving Cyclic Transition States / 6.8.3.：

Organometallic Compounds of the Group I, II, and III Metals / Chapter 7.：

Preparation and Properties / 7.1.：

Reactions of Organomagnesium and Organolithium Compounds / 7.2.：

Reactions with Alkylating Agents / 7.2.1.：

Reactions with Carbonyl Compounds / 7.2.2.：

Organic Derivatives of Group IIB and Group IIIB Metals / 7.3.：

Organozinc Compounds / 7.3.1.：

Organocadmium Compounds / 7.3.2.：

Organomercury Compounds / 7.3.3.：

Organoindium Reagents / 7.3.4.：

Organolanthanide Reagents / 7.4.：

Reactions Involving the Transition Metals / Chapter 8.：

Organocopper Intermediates / 8.1.：

Preparation and Structure of Organocopper Reagents / 8.1.1.：

Reactions Involving Organocopper Reagents and Intermediates / 8.1.2.：

Reactions Involving Organopalladium Intermediates / 8.2.：

Palladium-Catalyzed Nucleophilic Substitution and Alkylation / 8.2.1.：

The Heck Reaction / 8.2.2.：

Palladium-Catalyzed Cross Coupling / 8.2.3.：

Carbonylation Reactions / 8.2.4.：

Reactions Involving Organonickel Compounds / 8.3.：

Reactions Involving Rhodium and Cobalt / 8.4.：

Organometallic Compounds with [pi] Bonding / 8.5.：

Carbon--Carbon Bond-Forming Reactions of Compounds of Boron, Silicon, and Tin / Chapter 9.：

Organoboron Compounds / 9.1.：

Synthesis of Organoboranes / 9.1.1.：

Carbon--Carbon Bond-Forming Reactions of Organoboranes / 9.1.2.：

Organosilicon Compounds / 9.2.：

Synthesis of Organosilanes / 9.2.1.：

Carbon--Carbon Bond-Forming Reactions / 9.2.2.：

Organotin Compounds / 9.3.：

Synthesis of Organostannanes / 9.3.1.：

Reactions Involving Carbocations, Carbenes, and Radicals as Reactive Intermediates / 9.3.2.：

Reactions Involving Carbocation Intermediates / 10.1.：

Carbon-Carbon Bond Formation Involving Carbocations / 10.1.1.：

Rearrangement of Carbocations / 10.1.2.：

Related Rearrangements / 10.1.3.：

Fragmentation Reactions / 10.1.4.：

Reactions Involving Carbenes and Nitrenes / 10.2.：

Structure and Reactivity of Carbenes / 10.2.1.：

Generation of Carbenes / 10.2.2.：

Addition Reactions / 10.2.3.：

Insertion Reactions / 10.2.4.：

Generation and Reactions of Ylides by Carbenoid Decomposition / 10.2.5.：

Rearrangement Reactions / 10.2.6.：

Related Reactions / 10.2.7.：

Nitrenes and Related Intermediates / 10.2.8.：

Rearrangements to Electron-Deficient Nitrogen / 10.2.9.：

Reactions Involving Free-Radical Intermediates / 10.3.：

Sources of Radical Intermediates / 10.3.1.：

Introduction of Functionality by Radical Reactions / 10.3.2.：

Addition Reactions of Radicals to Substituted Alkenes / 10.3.3.：

Cyclization of Free-Radical Intermediates / 10.3.4.：

Fragmentation and Rearrangement Reactions / 10.3.5.：

Aromatic Substitution Reactions / Chapter 11.：

Electrophilic Aromatic Substitution / 11.1.：

Nitration / 11.1.1.：

Halogenation / 11.1.2.：

Friedel-Crafts Alkylations and Acylations / 11.1.3.：

Electrophilic Metalation / 11.1.4.：

Nucleophilic Aromatic Substitution / 11.2.：

Aryl Diazonium Ions as Synthetic Intermediates / 11.2.1.：

Substitution by the Addition-Elimination Mechanism / 11.2.2.：

Substitution by the Elimination-Addition Mechanism / 11.2.3.：

Transition-Metal-Catalyzed Substitution Reactions / 11.2.4.：

Aromatic Radical Substitution Reactions / 11.3.：

Substitution by the S[subscript RN]1 Mechanism / 11.4.：

Oxidations / Chapter 12.：

Oxidation of Alcohols to Aldehydes, Ketones, or Carboxylic Acids / 12.1.：

Transition-Metal Oxidants / 12.1.1.：

Other Oxidants / 12.1.2.：

Addition of Oxygen at Carbon-Carbon Double Bonds / 12.2.：

Epoxides from Alkenes and Peroxidic Reagents / 12.2.1.：

Transformations of Epoxides / 12.2.3.：

Reaction of Alkenes with Singlet Oxygen / 12.2.4.：

Cleavage of Carbon-Carbon Double Bonds / 12.3.：

Oxonolysis / 12.3.1.：

Selective Oxidative Cleavages at Other Functional Groups / 12.4.：

Cleavage of Glycols / 12.4.1.：

Oxidative Decarboxylation / 12.4.2.：

Oxidation of Ketones and Aldehydes / 12.5.：

Oxidation of Ketones and Aldehydes by Oxygen and Peroxidic Compounds / 12.5.1.：

Oxidation with Other Reagents / 12.5.3.：

Allylic Oxidation / 12.6.：

Oxidations at Unfunctionalized Carbon / 12.6.1.：

Planning and Execution of Multistep Syntheses / Chapter 13.：

Protective Groups / 13.1.：

Hydroxyl-Protecting Groups / 13.1.1.：

Amino-Protecting Groups / 13.1.2.：

Carbonyl-Protecting Groups / 13.1.3.：

Carboxylic Acid-Protecting Groups / 13.1.4.：

Synthetic Equivalent Groups / 13.2.：

Synthetic Analysis and Planning / 13.3.：

Control of Stereochemistry / 13.4.：

Illustrative Syntheses / 13.5.：

Juvabione / 13.5.1.：

Longifolene / 13.5.2.：

Prelog-Djerassi Lactone / 13.5.3.：

Taxol / 13.5.4.：

Epothilone A / 13.5.5.：

Solid-Phase Synthesis / 13.6.：

Solid-Phase Synthesis of Polypeptides / 13.6.1.：

Solid-Phase Synthesis of Oligonucleotides / 13.6.2.：

Combinatorial Synthesis / 13.7.：

References for Problems

Index

Alkylation of Nucleophilic Carbon Intermediates / Chapter 1.：

Generation of Carbanions by Deprotonation / 1.1.：

Regioselectivity and Stereoselectivity in Enolate Formation / 1.2.：

Other Means of Generating Enolates / 1.3.：

Alkylation of Enolates / 1.4.：

Generation and Alkylation of Dianions / 1.5.：

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