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Reaction and Synthesis

ISBN-10: 0306462451

ISBN-13: 9780306462450

Edition: 4th 2001 (Revised)

Authors: Francis A. Carey, Richard J. Sundberg

List price: $49.50
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Description:

The control of reactivity to achieve specific syntheses is one of the overarching goals of organic chemistry. In the decade since the publication of the third edition, major advances have been made in the development of efficient new methods, particularly catalytic processes, and in means for control of reaction stereochemistry. This volume assumes a level of familiarity with structural and mechanistic concepts comparable to that in the companion volume, Part A, Structures and Mechanisms. Together, the two volumes are intended to provide the advanced undergraduate or beginning graduate student in chemistry with a sufficient foundation to comprehend and use the research literature in organic chemistry.
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Book details

List price: $49.50
Edition: 4th
Copyright year: 2001
Publisher: Springer
Publication date: 6/30/2002
Binding: Paperback
Pages: 958
Size: 7.00" wide x 10.00" long x 2.25" tall
Weight: 4.488
Language: English

Francis A. Carey is a native of Pennsylvania, educated in the public schools of Philadelphia, at Drexel University (B.S. in chemistry, 1959), and at Penn State (Ph.D. 1963). Following postdoctoral work at Harvard and military service, he was appointed to the chemistry faculty of the University of Virginia in 1966. Prior to retiring in 2000, he regularly taught the two-semester lecture courses in general chemistry and organic chemistry. With his students, Professor Carey has published over forty research papers in synthetic and mechanistic organic chemistry. In addition to this text, he is coauthor (with Robert C. Atkins) of Organic Chemistry: A Brief Course and (with Richard J. Sundberg) of Advanced Organic Chemistry, a two-volume treatment designed for graduate students and advanced undergraduates. He was a member of the Committee of Examiners of The Graduate Record Examination in Chemistry from 1993-2000. Frank and his wife Jill, who is a teacher/director of a preschool and a church organist, are the parents of Andy, Bob, and Bill and the grandparents of Riyad and Ava.

Alkylation of Nucleophilic Carbon Intermediates
Generation of Carbanions by Deprotonation
Regioselectivity and Stereoselectivity in Enolate Formation
Other Means of Generating Enolates
Alkylation of Enolates
Generation and Alkylation of Dianions
Medium Effects in the Alkylation of Enolates
Oxygen versus Carbon as the Site of Alkylation
Alkylation of Aldehydes, Esters, Amides, and Nitriles
The Nitrogen Analogs of Enols and Enolates--Enamines and Imine Anions
Alkylation of Carbon Nucleophiles by Conjugate Addition
General References
Problems
Reaction of Carbon Nucleophiles with Carbonyl Groups
Aldol Addition and Condensation Reactions
The General Mechanism
Mixed Aldol Condensations with Aromatic Aldehydes
Control of Regiochemistry and Stereochemistry of Mixed Aldol Reactions of Aliphatic Aldehydes and Ketones
Intramolecular Aldol Reactions and the Robinson Annulation
Addition Reactions of Imines and Iminium Ions
The Mannich Reaction
Amine-Catalyzed Condensation Reactions
Acylation of Carbanions
The Wittig and Related Reactions of Phosphorus-Stabilized Carbon Nucleophiles
Reactions of Carbonyl Compounds with [alpha]-Trimethylsilylcarbanions
Sulfur Ylides and Related Nucleophiles
Nucleophilic Addition--Cyclization
General References
Problems
Functional Group Interconversion by Nucleophilic Substitution
Conversion of Alcohols to Alkylating Agents
Sulfonate Esters
Halides
Introduction of Functional Groups by Nucleophilic Substitution at Saturated Carbon
General Solvent Effects
Nitriles
Azides
Oxygen Nucleophiles
Nitrogen Nucleophiles
Sulfur Nucleophiles
Phosphorus Nucleophiles
Summary of Nucleophilic Substitution at Saturated Carbon
Nucleophilic Cleavage of Carbon-Oxygen Bonds in Ethers and Esters
Interconversion of Carboxylic Acid Derivatives
Preparation of Reactive Reagents for Acylation
Preparation of Esters
Preparation of Amides
Problems
Electrophilic Additions to Carbon--Carbon Multiple Bonds
Addition of Hydrogen Halides
Hydration and Other Acid-Catalyzed Additions of Oxygen Nucleophiles
Oxymercuration
Addition of Halogens to Alkenes
Electrophilic Sulfur and Selenium Reagents
Addition of Other Electrophilic Reagents
Electrophilic Substitution Alpha to Carbonyl Groups
Additions to Allenes and Alkynes
Addition at Double Bonds via Organoborane Intermediates
Hydroboration
Reactions of Organoboranes
Enantioselective Hydroboration
Hydroboration of Alkynes
General References
Problems
Reduction of Carbonyl and Other Functional Groups
Addition of Hydrogen
Catalytic Hydrogenation
Other Hydrogen-Transfer Reagents
Group III Hydride-Donor Reagents
Reduction of Carbonyl Compounds
Stereoselectivity of Hydride Reduction
Reduction of Other Functional Groups by Hydride Donors
Group IV Hydride Donors
Hydrogen-Atom Donors
Dissolving-Metal Reductions
Addition of Hydrogen
Reductive Removal of Functional Groups
Reductive Carbon--Carbon Bond Formation
Reductive Deoxygenation of Carbonyl Groups
Reductive Elimination and Fragmentation
General References
Problems
Cycloadditions, Unimolecular Rearrangements, and Thermal Eliminations
Cycloaddition Reactions
The Diels--Alder Reaction: General Features
The Diels--Alder Reaction: Dienophiles
The Diels--Alder Reaction: Dienes
Asymmetric Diels--Alder Reactions
Intramolecular Diels--Alder Reactions
Dipolar Cycloaddition Reactions
[2 + 2] Cycloadditions and Other Reactions Leading to Cyclobutanes
Photochemical Cycloaddition Reactions
[3,3] Sigmatropic Rearrangements
Cope Rearrangements
Claisen Rearrangements
[2,3] Sigmatropic Rearrangements
Ene Reactions
Unimolecular Thermal Elimination Reactions
Cheletropic Elimination
Decomposition of Cyclic Azo Compounds
[beta] Eliminations Involving Cyclic Transition States
General References
Problems
Organometallic Compounds of the Group I, II, and III Metals
Preparation and Properties
Reactions of Organomagnesium and Organolithium Compounds
Reactions with Alkylating Agents
Reactions with Carbonyl Compounds
Organic Derivatives of Group IIB and Group IIIB Metals
Organozinc Compounds
Organocadmium Compounds
Organomercury Compounds
Organoindium Reagents
Organolanthanide Reagents
General References
Problems
Reactions Involving the Transition Metals
Organocopper Intermediates
Preparation and Structure of Organocopper Reagents
Reactions Involving Organocopper Reagents and Intermediates
Reactions Involving Organopalladium Intermediates
Palladium-Catalyzed Nucleophilic Substitution and Alkylation
The Heck Reaction
Palladium-Catalyzed Cross Coupling
Carbonylation Reactions
Reactions Involving Organonickel Compounds
Reactions Involving Rhodium and Cobalt
Organometallic Compounds with [pi] Bonding
General References
Problems
Carbon--Carbon Bond-Forming Reactions of Compounds of Boron, Silicon, and Tin
Organoboron Compounds
Synthesis of Organoboranes
Carbon--Carbon Bond-Forming Reactions of Organoboranes
Organosilicon Compounds
Synthesis of Organosilanes
Carbon--Carbon Bond-Forming Reactions
Organotin Compounds
Synthesis of Organostannanes
Carbon--Carbon Bond-Forming Reactions
General References
Problems
Reactions Involving Carbocations, Carbenes, and Radicals as Reactive Intermediates
Reactions Involving Carbocation Intermediates
Carbon-Carbon Bond Formation Involving Carbocations
Rearrangement of Carbocations
Related Rearrangements
Fragmentation Reactions
Reactions Involving Carbenes and Nitrenes
Structure and Reactivity of Carbenes
Generation of Carbenes
Addition Reactions
Insertion Reactions
Generation and Reactions of Ylides by Carbenoid Decomposition
Rearrangement Reactions
Related Reactions
Nitrenes and Related Intermediates
Rearrangements to Electron-Deficient Nitrogen
Reactions Involving Free-Radical Intermediates
Sources of Radical Intermediates
Introduction of Functionality by Radical Reactions
Addition Reactions of Radicals to Substituted Alkenes
Cyclization of Free-Radical Intermediates
Fragmentation and Rearrangement Reactions
General References
Problems
Aromatic Substitution Reactions
Electrophilic Aromatic Substitution
Nitration
Halogenation
Friedel-Crafts Alkylations and Acylations
Electrophilic Metalation
Nucleophilic Aromatic Substitution
Aryl Diazonium Ions as Synthetic Intermediates
Substitution by the Addition-Elimination Mechanism
Substitution by the Elimination-Addition Mechanism
Transition-Metal-Catalyzed Substitution Reactions
Aromatic Radical Substitution Reactions
Substitution by the S[subscript RN]1 Mechanism
General References
Problems
Oxidations
Oxidation of Alcohols to Aldehydes, Ketones, or Carboxylic Acids
Transition-Metal Oxidants
Other Oxidants
Addition of Oxygen at Carbon-Carbon Double Bonds
Transition-Metal Oxidants
Epoxides from Alkenes and Peroxidic Reagents
Transformations of Epoxides
Reaction of Alkenes with Singlet Oxygen
Cleavage of Carbon-Carbon Double Bonds
Transition-Metal Oxidants
Oxonolysis
Selective Oxidative Cleavages at Other Functional Groups
Cleavage of Glycols
Oxidative Decarboxylation
Oxidation of Ketones and Aldehydes
Transition-Metal Oxidants
Oxidation of Ketones and Aldehydes by Oxygen and Peroxidic Compounds
Oxidation with Other Reagents
Allylic Oxidation
Transition-Metal Oxidants
Other Oxidants
Oxidations at Unfunctionalized Carbon
General References
Problems
Planning and Execution of Multistep Syntheses
Protective Groups
Hydroxyl-Protecting Groups
Amino-Protecting Groups
Carbonyl-Protecting Groups
Carboxylic Acid-Protecting Groups
Synthetic Equivalent Groups
Synthetic Analysis and Planning
Control of Stereochemistry
Illustrative Syntheses
Juvabione
Longifolene
Prelog-Djerassi Lactone
Taxol
Epothilone A
Solid-Phase Synthesis
Solid-Phase Synthesis of Polypeptides
Solid-Phase Synthesis of Oligonucleotides
Combinatorial Synthesis
General References
Problems
References for Problems
Index