Advanced Organic Synthesis - 1st Edition - ISBN: 9780125049504, 9780323159975

Advanced Organic Synthesis

1st Edition

Methods and Techniques

Authors: Richard Monson
eBook ISBN: 9780323159975
Imprint: Academic Press
Published Date: 1st January 1971
Page Count: 216
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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


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


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Richard Monson

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