Advanced Organic Chemistry: Reactions and Synthesis / Edition 3

Advanced Organic Chemistry: Reactions and Synthesis / Edition 3

by Francis A. Carey, Richard J. Sundberg, Richard J. Sundberg

ISBN-10: 0306434571

ISBN-13: 9780306434570

Pub. Date: 09/01/1990

Publisher: Springer-Verlag New York, LLC

Product Details

Springer-Verlag New York, LLC
Publication date:
Advanced Organic Chemistry Series
Edition description:
Older Edition
Product dimensions:
7.14(w) x 9.98(h) x 1.82(d)

Related Subjects

Table of Contents

List of Figures
List of Tables
List of Schemes
Chapter 1. Alkylation of Nucleophilic Carbon. Enolates and Enamines
1.1. Generation of Carbanions by Deprotonation
1.2. Regioselectivity and Stereoselectivity in Enolate Formation
1.3. Other Means of Generating Enolates
1.4. Alkylation of Enolates
1.5. Generation and Alkylation of Dianions
1.6. Medium Effects in the Alkylation of Enolates
1.7. Oxygen versus Carbon as the Site of Alkylation
1.8. Alkylation of Aldehydes, Esters, Amides, and Nitriles
1.9. The Nitrogen Analogs of Enols and Enolates--Enamines and Imine Anions
1.10. Alkylation of Carbon Nucleophiles by Conjugate Addition
General References
Chapter 2. Reactions of Carbon Nucleophiles with Carbonyl Groups
2.1. Aldol Condensation
2.1.1. The General Mechanism
2.1.2. Mixed Aldol Condensations with Aromatic Aldehydes
2.1.3. Control of Regiochemistry and Stereochemistry of Mixed Aldol Condensations of Aliphatic Aldehydes and Ketones
2.1.4. Intramolecular Aldol Condensations and the Robinson Annulation
2.2. Condensation Reactions of Imines and Iminium Ions
2.2.1. The Mannich Reaction
2.2.2. Amine-Catalyzed Condensation Reactions
2.3. Acylation of Carbanions
2.4. The Witting and Related Reactions
2.5. Reactions of Carbonyl Compounds with a-Trimethylsilyl Carbanions
2.6. Sulfur Ylides and Related Nucleophiles
2.7. Nucleophilic Addition-Cyclization
General References
Chapter 3. Functional Group Interconversion by Nucleophilic Substitution
3.1. Conversion of Alcohols to Alkylating Agents
3.1.1. Sulfonate Esters
3.1.2. Halides
3.2. Introduction of Functional Groups by Nucleophilic Substitution at Saturated Carbon
3.2.1. General Solvent Effects
3.2.2. Nitriles
3.2.3. Azides
3.2.4. Alkylation of Amines and Amides
3.2.5. Oxygen Nucleophiles
3.2.6. Sulfur Nucleophiles
3.2.7. Phosphorus Nucleophiles
3.2.8. Summary of Nucleophilic Substitution at Saturated Carbon
3.3. Nucleophilic Cleavage of Carbon-Oxygen Bonds in Ethers and Esters
3.4. Interconversion of Carboxylic Acid Derivatives
3.4.1. Preparation of Reaction Reagents for Acylation
3.4.2. Preparation of Esters
3.4.3. Preparation of Amides
Chapter 4. Electrophilic Additions to Carbon-Carbon Multiple Bonds
4.1. Addition of Hydrogen Halides
4.2. Hydration and Other Acid-Catalyzed Additions
4.3. Oxymercuration
4.4. Addition of Halogens to Alkenes
4.5. Electrophilic Sulfur and Selenium Reagents
4.6. Addition of Other Electrophilic Reagents
4.7. Electrophilic Substitution Alpha to Carbonyl Groups
4.8. Additions to Allenes and Alkynes
4.9. Addition at Double Bonds via Organoboranes
4.9.1. Hydroboration
4.9.2. Reactions of Organoboranes
4.9.3. Enantioselective Hydroboration
4.9.4. Hydroboration of Alkynes
General References
Chapter 5. Reduction of Carbonyl and Other Functional Groups
5.1. Addition of Hydrogen
5.1.1. Catalytic Hydrogenation
5.1.2. Other Hydrogen-Transfer Reagents
5.2. Group III Hydride-Donor Reagents
5.2.1. Reduction of Carbonyl Compounds
5.2.2. Reduction of Other Functional Groups by Hydride Donors
5.3. Group IV Hydride Donors
5.4. Hydrogen Atom Donors
5.5. Dissolving-Metal Reductions
5.5.1. Addition of Hydrogen
5.5.2. Reductive Removal of Functional Groups
5.5.3. Reductive Carbon-Carbon Bond Formation
5.6. Reductive Deoxygenation of Carbonyl Groups
General References
Chapter 6. Cycloaddition, Unimolecular Rearrangements, and Thermal Eliminations
6.1. Cycloaddition Reactions
6.1.1. The Diels-Alder Reaction: General Features
6.1.2. The Diels-Alder Reaction: Dienophiles
6.1.3. The Diels-Alder Reaction: Dienes
6.1.4. Intramolecular Diels-Alder Reactions
6.2. Dipolar Cycloaddition Reactions
6.3. [2 + 2] Cycloadditions and Other Reactions Leading to Cyclobutanes
6.4. Photochemical Cycloaddition Reactions
6.5. [3,3]-Sigmatropic Rearrangements: Cope and Claisen Rearrangements
6.6. [2,3]-Sigmatropic Rearrangements
6.7. Ene Reactions
6.8. Unimolecular Thermal Elimination Reactions
6.8.1. Cheletropic Elimination
6.8.2. Decomposition of Cyclic Azo Compounds
6.8.3. \xDF-Eliminations Involving Cyclic Transition States
General References
Chapter 7. Organometallic Compounds of Group I and II Metals
7.1. Preparation and Properties of Organolithium and Organomagnesium Compounds
7.2. Reactions of Organolithium and Organomagnesium Compounds
7.2.1. Reactions with Alkylating Agents
7.2.2. Reactions with Carbonyl Compounds
7.3. Organic Derivatives of Group IIB Metals
7.3.1. Organozinc Compounds
7.3.2. Organocadmium Compounds
7.3.3. Organomercury Compounds
7.4. Organocerium Compounds
General References
Chapter 8. Reactions Involving the Transition Metals
8.1. Reactions Involving Organocopper Intermediates
8.2. Reactions Involving Organopalladium Intermediates
8.3. Reactions Involving Organonickel Compounds
8.4. Reactions Involving Rhodium, Iron, and Cobalt
8.5. Organometallic Compounds with p Bonding
General References
Chapter 9. Carbon-Carbon Bond-Forming Reactions of Compounds of Boron, Silicon, and Tin
9.1. Organoboron Compounds
9.1.1. Synthesis of Organoboranes
9.1.2. Carbon-Carbon Bond-Forming Reactions
9.2. Organosilicon Compounds
9.2.1. Synthesis of Organosilanes
9.2.2. Carbon-Carbon Bond-Forming Reactions
9.3. Organotin Compounds
9.3.1. Synthesis of Organostannanes
9.3.2. Carbon-Carbon Bond-Forming Reactions
General References
Chapter 10. Reactions Involving Highly Reactive Electron-Deficient Intermediates
10.1. Reactions Involving Carbocation Intermediates
10.1.1. Carbon-Carbon Bond-Formation Involving Carbocations
10.1.2. Rearrangements of Carbocations
10.1.3. Related Rearrangements
10.1.4. Fragmentation Reactions
10.2. Reactions Involving Carbenes and Nitrenes
10.2.1. Structure and Reactivity of Carbenes
10.2.2. Generation of Carbenes
10.2.3. Addition Reactions
10.2.4. Insertion Reactions
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
10.3. Reactions Involving Free-Radical Intermediates
10.3.1. Sources of Radical Intermediates
10.3.2. Introduction of Functionality by Radical Reactions
10.3.3. Addition Reactions of Radicals with Substituted Alkenes
10.3.4. Cyclization of Free-Radical Intermediates
10.3.5. Fragmentation and Rearrangement Reactions
General References
Chapter 11. Aromatic Substitution Reactions
11.1. Electrophilic Aromatic Substitution
11.1.1. Nitration
11.1.2. Halogenation
11.1.3. Friedel-Crafts Alkylations and Acylations
11.1.4. Electrophilic Metalation
11.2. Nucleophilic Aromatic Substitution
11.2.1. Aromatic Diazonium Ions as Synthetic Intermediates
11.2.2. Substitution by the Addition-Elimination Mechanism
11.2.3. Substitution by the Elimination-Addition Mechanism
11.2.4. Copper-Catalyzed Reactions
11.3. Aromatic Radical Substitution Reactions
11.4. Substitution by the SRN1 Mechanism
Chapter 12. Oxidations
12.1. Oxidation of Alcohols to Aldehydes, Ketones, or Carboxylic Acids
12.1.1. Transition Metal Oxidants
12.1.2. Other Oxidants
12.2. Addition of Oxygen at Carbon-Carbon Double Bonds
12.2.1. Transition Metal Oxidants
12.2.2. Epoxides from Alkenes and Peroxidic Reagents
12.2.3. Subsequent Transformations of Epoxides
12.2.4. Reactions of Alkenes with Singlet Oxygen
12.3. Cleavage of Carbon-Carbon Double Bonds
12.3.1. Transition Metal Oxidants
12.3.2. Ozonolysis
12.4. Selective Oxidative Cleavages at Other Functional Groups
12.4.1. Cleavage of Glycols
12.4.2. Oxidative Decarboxylation
12.5. Oxidation of Ketones and Aldehydes
12.5.1. Transition Metal Oxidants
12.5.2. Oxidation of Ketones and Aldehydes by Oxygen and Peroxidic Compounds
12.5.3. Oxidation with Other Reagents
12.6. Allylic Oxidation
12.6.1. Transition Metal Oxidants
12.6.2. Other Oxidants
12.7. Oxidations at Unfunctionalized Carbon
General References
Chapter 13. Multistep Syntheses
13.1. Protective Groups
13.1.1. Hydroxyl-Protecting Groups
13.1.2. Amino-Protecting Groups
13.1.3. Carbonyl-Protecting Groups
13.1.4. Carboxy Acid-Protecting Groups
13.2. Synthetic Equivalent Groups
13.3. Synthetic Analysis and Planning
13.4. Control of Stereochemistry
13.5. Illustrative Syntheses
13.5.1. Juvabione
13.5.2. Longifolene
13.5.3. Prelog-Djerassi Lactone
13.5.4. Aphidicolin
General References
References for Problems

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