Organomagnesium Methods in Organic Chemistry

by Wakefield

• ISBN13: 9780127309453
• ISBN10: 0127309454
• Edition: 1st
• Format: Hardcover
• Copyright: 1995-04-12
• Publisher: Elsevier Science

Summary

The book opens with a general overview of the constitution and reactivity of organomagnesium compounds, followed by information on handling them and on their detection and estimation. Throughout, practical aspects aswell as principles are emphasized. The chapters on the synthesis of organomagnesium compounds cover the preparation of special forms of metallic magnesium and the reaction of magnesium with substrates such as dienes, as well as the traditional preparation of Grignard reagents. Preparations by metallation and metal-halogen exchanges are also included, as are newer methods such as hydromagnesiation of alkenes and alkynes. Systematic coverage is provided on synthetically useful reactions of organomagnesium compounds. Of fundamental importance in organic synthesis are carbon-carbon bond forming reactions; additions to carbon-carbon, carbon-nitrogen, carbon-oxygen, and carbon-sulfur multiple bonds; and nucleophilic substitution at carbon. The formation of carbon-heteroatom bonds in organic compounds is described, where the heteroatom is hydrogen, nitrogen, oxygen, sulfur, or halogen. Finally, the use of organomagnesium compounds in preparing other organometalloid and organometallic compounds is outlined. Representative experimental procedures are included throughout the book, and tables with references to well-described examples are provided. Key Features * Presents a general overview of the constitution and reactivity of organomagnesium compounds * Provides coverage on the detection and estimation of organomagnesium compounds * Emphasizes practical aspects as well as principles * Covers the preparation of special forms of metallic magnesium and the reaction of magnesium with substrates such as dienes * Includes preparations by metallation and metal-halogen exchanges * Reviews new preparation methods such as hydromagnesiation of alkenes and alkynes * Outlines information on synthetically useful reactions of organomagnesium compounds * Describes the formation of carbon-heteroatom bonds in organic compounds * Addresses the use of organomagnesium compounds in preparing other organometalloid and organometallic compounds * Includes representative procedures and tables with references to well-described examples

Table of Contents

Introduction and General References

General Considerations in the Application of Organomagnesium Compounds in Organic and Organometallic Synthesis

Preparation of Organomagnesium Compounds

Addition of Organomagnesium Compounds to Carbon-Carbon Multiple Bonds

Addition of Organomagnesium Compounds to Carbon-Nitrogen Multiple Bonds

Addition of Organomagnesium Compounds to Carbonyl Groups

Carbophilic Addition of Organomagnesium Compounds to Thiocarbonyl Groups

Substitution atCarbon by Organomagnesium Compounds

Carbenoid and Arynoid Reactions of Organomagnesium Compounds

Reactions of Organomagnesium Compounds with Proton Donors

Formation of Carbon-Nitrogen Bonds via Organomagnesium Compounds

Formation of Carbon-Oxygen Bonds via Organomagnesium Compounds

Formation of Carbon-Sulfur, Carbon-Selenium, and Carbon-Tellurium Bonds via Organomagnesium Compounds

Formation of Carbon-Halogen Bonds via Organomagnesium Compounds

Synthesis of Organoboron, Organosilicon, and Organophosphorous Compounds from Organomagnesium Compounds

Organomagnesium Compounds in the Synthesis of Other Organometallic Compounds

Index of Compounds and Methods

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