文档介绍：anic Synthesis
METHODS AND TECHNIQUES
RICHARD S. MONSON
DEPARTMENT OF CHEMISTRY
CALIFORNIA STATE COLLEGE, HAYWARD
HAYWARD, CALIFORNIA
ACADEMIC PRESS
New York and London
COPYRIGHT © 1971, BY ACADEMIC PRESS, INC.
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Contents
Preface xi
I. FUNCTIONAL GROUP MODIFICATIONS
1. Chemical Oxidations
I. Chromium Trioxide Oxidation 3
II. Periodate-Permanganate Cleavage of Olefins 5
III. Free Radical Oxidation of an Allylic Position 7
IV. Epoxidation of Olefins 8
V. Baeyer-Villiger Oxidation of Ketones 9
VI. Lead Tetraacetate Oxidation of Cycloalkanols 11
VII. Photolytic Conversion of Cyclohexane to Cyclohexanone Oxime 11
VIII. Oxidation of Ethers to Esters 12
IX. Partial Oxidation of an Aliphatic Side Chain 13
X. Bisdecarboxylation with Lead Tetraacetate 14
XI. Oxidation with Selenium Dioxide 15
References 16
2. Hydride and Related Reductions
I. Reduction by Lithium Aluminum Hydride 18
II. Mixed Hydride Reduction 20
III. Reduction with Iridium-Containing Catalysts 22
IV. Reduction of Conjugated Alkenes with Chromium (H) Sulfate 23
References 24
3. Dissolving Metal Reductions
I. Reduction by Lithium-Amine 25
II. Reduction by Lithium-Ethylenediamine 26
III. Reduction of a,/MJnsaturated Ketones by Lithium-Ammonia 27
IV. Reduction of a,/9-Unsaturated Ketones in Hexamethylphosphoric Triamide .... 28
V. Reduction of an a,/?-Unsaturated y-Diketone with Zinc 29
References 30
VI CONTENTS
4. Hydroboration
I. Hydroboration of Olefins as a Route to Alcohols 32
II. Selective