Advanced Organic Synthesis: Methods and Techniques

by Richard Monson

Overview

Advanced Organic Synthesis: Methods and Techniques presents a survey and systematic introduction to the modern techniques of organic synthesis. The book attempts to acquaint the reader with a variety of laboratory techniques as well as introduce chemical reagents that require deftness and care in handling. Chapters are devoted that discuss the techniques of organic synthesis; apparatus and terminology used in the description of synthetic procedures; the scope and mechanism of chemical reactions; and technical procedures on how to perform chemical experiments. The text will be of vital importance to advanced undergraduate student or beginning graduate student of chemistry.

Product Details

ISBN-13:	9780323159975
Publisher:	Elsevier Science & Technology Books
Publication date:	12/02/2012
Sold by:	Barnes & Noble
Format:	eBook
Pages:	216
File size:	6 MB

Table of Contents

PrefaceI. Functional Group Modifications 1. Chemical Oxidations I. Chromium Trioxide Oxidation II. Periodate—Permanganate Cleavage of Olefins III. Free Radical Oxidation of an Allylic Position IV. Epoxidation of Olefins V. Baeyer-Villiger Oxidation of Ketones VI. Lead Tetraacetate Oxidation of Cycloalkanols VII. Photolytic Conversion of Cyclohexane to Cyclohexanone Oxime VIII. Oxidation of Ethers to Esters IX. Partial Oxidation of an Aliphatic Side Chain X. Bisdecarboxylation with Lead Tetraacetate XI. Oxidation with Selenium Dioxide References 2. Hydride and Related Reductions I. Reduction by Lithium Aluminum Hydride II. Mixed Hydride Reduction III. Reduction with Iridium-Containing Catalysts IV. Reduction of Conjugated Alkenes with Chromium (II) Sulfate References 3. Dissolving Metal Reductions I. Reduction by Lithium—Amine II. Reduction by Lithium—Ethylenediamine III. Reduction of α,β-Unsaturated Ketones by Lithium—Ammonia IV. Reduction of α,β-Unsaturated Ketones in Hexamethylphosphoric Triamide V. Reduction of an α,β-Unsaturated Υ-Diketone with Zinc References 4. Hydroboration I. Hydroboration of Olefins as a Route to Alcohols II. Selective Hydroborations Using Bis(3-Methyl-2-Butyl)Borane (BMB) III. Purification of a Mixture of Δ9,10- and Δ1(9)-Octalins References 5. Catalytic Hydrogenation I. Hydrogenation Over Platinum Catalyst II. Low-Pressure Hydrogenation of Phenols Over Rhodium Catalysts III. Cis-4-Hydroxycyclohexanecarboxylic Acid from p-Hydroxybenzoic Acid IV. 3-Isoquinuclidone from p-Aminobenzoic Acid V. Homogeneous Catalytic Hydrogenation References 6. The Introduction of Halogen I. Halides from Alcohols by Triphenylphosphine—Carbon Tetrahalide II. Halides from Alcohols and Phenols by Triphenylphosphine Dihalide III. Allylic and Benzylic Bromination with N-Bromosuccinimide IV. α-Bromination of Ketones and Dehydrobromination V. Stereospecific Synthesis of Trans-4-Halocyclohexanols References 7. Miscellaneous Elimination, Substitution, and Addition Reactions I. Methylenecyclohexane by Pyrolysis of an Amine Oxide II. The Wolff-Kishner Reduction III. Dehydration of 2-Decalol IV. Boron Trifluoride Catalyzed Hydrolysis of Nitriles V. Bridged Sulfides by Addition of Sulfur Dichloride to Dienes VI. Methylation by Diazomethane VII. Oxymercuration: A Convenient Route to Markovnikov Hydration of Olefins VIII. Esterification of Tertiary Alcohols IX. Ketalization X. Half-Esterification of a Diol XI. Substitution on Ferrocene XII. Demethylation of Aryl Methyl Ethers by Boron Tribromide ReferencesII. Skeletal Modifications 8. The Diels-Alder Reaction I. 3,6-Diphenyl-4,5-Cyclohexenedicarboxylic Anhydride II. Reactions with Butadiene III. Catalysis by Aluminum Chloride IV. Generation of Dienes from Diones V. Reactions with Cyclopentadiene References 9. Enamines as Intermediates I. Preparation of the Morpholine Enamine of Cyclohexanone II. Acylation of Enamines III. Enamines as Michael Addition Reagents IV. Reactions of Enamines with β-Propiolactone V. Reactions of Enamines with Acrolein References 10. Enolate Ions as Intermediates I. Ketones as Enolates: Carbethoxylation of Cyclic Ketones II. Esters as Enolates: 1,4-Cyclohexanedione and Meerwein's Ester III. Methylsulfinyl Carbanion as a Route to Methyl Ketones IV. Cyclization with Diethyl Malonate V.