Organomagnesium Methods in Organic Chemistry

Basil J. Wakefield

• Publisher: Academic Press
• Year: 1995
• Print ISBN: 9780127309453
• eBook ISBN: 9780080538174
• Topic: Naturwissenschaften
• Subtopic: Organische Chemie

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. - 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

• Front Cover
• Organomagnesium Methods in Organic Synthesis
• Copyright Page
• Contents
• Foreword
• Preface
• Detailed Contents
• Abbreviations
• Chapter 1. Introduction and General References
• Chapter 2. General Considerations in the Application of Organomagnesium Compounds in Organic and Organometallic Synthesis
• Chapter 3. Preparation of Organomagnesium Compounds
• Chapter 4. Addition of Organomagnesium Compounds to Carbon–Carbon Multiple Bonds
• Chapter 5. Addition of Organomagnesium Compounds to Carbon–Nitrogen Multiple Bonds
• Chapter 6. Addition of Organomagnesium Compounds to Carbonyl Groups
• Chapter 7. Carbophilic Addition of Organomagnesium Compounds to Thiocarbonyl Groups
• Chapter 8. Substitution at Carbon by Organomagnesium Compounds
• Chapter 9. Carbenoid and Arynoid Reactions of Organomagnesium Compounds
• Chapter 10. Reactions of Organomagnesium Compounds with Proton Donors
• Chapter 11. Formation of Carbon–Nitrogen Bonds via Organomagnesium Compounds
• Chapter 12. Formation of Carbon–Oxygen Bonds via Organomagnesium Compounds
• Chapter 13. Formation of Carbon–Sulfur, Carbon-Selenium and Carbon-Tellurium Bonds via Organomagnesium Compounds
• Chapter 14. Formation of Carbon–Halogen Bonds via Organomagnesium Compounds
• Chapter 15. Synthesis of Organoboron, Organosilicon and Organophosphorus Compounds from Organomagnesium Compounds
• Chapter 16. Organomagnesium Compounds in the Synihesis of Other Organometallic Compounds
• Index of Compounds and Methods