Advanced Organic Synthesis

Advanced Organic Synthesis

Methods and Techniques

1st Edition - January 1, 1971

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  • Author: Richard Monson
  • eBook ISBN: 9780323159975

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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.

Table of Contents

  • Preface

    I. 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


    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


    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


    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


    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


    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


    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


    II. 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


    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


    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. Carboxylations with Magnesium Methyl Carbonate (MMC)

    VI. Alkylationof β-Ketoesters

    VII. The Robinson Annelation Reaction


    11. The Wittig Reaction

    I. Benzyl-Containing Ylides

    II. Alkyl Ylides Requiring n-Butyl Lithium

    III. Methylsulfinyl Carbanion in the Generation of Ylides

    IV. The Wittig Reaction Catalyzed by Ethylene Oxide

    V. Cyclopropylidene Derivatives via the Wittig Reaction


    12. Reactions of Trialkylboranes

    I. Trialkylcarbinols from Trialkylboranes and Carbon Monoxide

    II. Dialkylketones from Trialkylboranes and Carbon Monoxide—Water

    III. The Reaction of Trialkylboranes with Methyl Vinyl Ketone and Acrolein

    IV. The Reaction of Trialkylboranes with Ethyl Bromoacetate


    13. Carbenes as Intermediates

    I. Carbene Addition by the Zinc-Copper Couple

    II. Dibromocarbenes

    III. Dihalocarbenes from Phenyl(trihalomethyl)mercury Compounds


    14. Ethynylation

    I. Generation of Sodium Acetylide in Liquid Ammonia

    II. The Generation of Sodium Acetylide in Tetrahydrofuran

    III. The Generation of Sodium Acetylide Via Dimsylsodium


    15. Structural Isomerizations

    I. Acid Catalyzed Rearrangement of Saturated Hydrocarbons

    II. Photolytic Ring Contraction

    III. Isomerization of 1-Ethynylcylohexanol: Three Methods

    IV. Photolytic Isomerization of 1,5-Cyclooctadiene

    V. Oxidative Rearrangement of β-Diketones

    VI. Base Catalyzed Rearrangement of 4-Benzoyloxycyclohexanone

    VII. Allenes from 1,1-Dihalocyclopropanes by Methyllithium


    16. Elimination, Substitution, and Addition Reactions Resulting in Carbon—Carbon Bond Formation

    I. Carboxylation of Carbonium Ions

    II. Paracyclophane via a 1,6-Hofmann Elimination

    III. Diphenylcyclopropenone from Commercial Dibenzyl Ketone

    IV. Phenylcyclopropane from Cinnamaldehyde

    V. Conversion of Alkyl Chlorides to Nitriles in DMSO

    VI. Photolytic Addition of Formamide to Olefins

    VII. Intermolecular Dehydrohalogenation

    VIII. Ring Enlargement with Diazomethane

    IX. Conjugate Addition of Grignard Reagents

    X. Dimethyloxosulfonium Methylide in Methylene Insertions

    XI. Acylation of a Cycloalkane: Remote Functionalization

    XII. The Modified Hunsdiecker Reaction


    17. Miscellaneous Preparations

    I. Derivatives of Adamantane

    II. Percarboxylic Acids

    III. Diazomethane

    IV. Trichloroisocyanuric Acid


    Appendix 1. Examples of Multistep Syntheses

    Appendix 2. Sources of Organic Reagents

    Appendix 3. Introduction to the Techniques of Synthesis

    I. The Reaction

    II. The Workup

    III. Purification of the Product


    Subject Index

Product details

  • No. of pages: 216
  • Language: English
  • Copyright: © Academic Press 1971
  • Published: January 1, 1971
  • Imprint: Academic Press
  • eBook ISBN: 9780323159975

About the Author

Richard Monson

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