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Organometallic Reaction Mechanisms Of The Nontransition Elements - 1st Edition - ISBN: 9780124811508, 9780323141222

Organometallic Reaction Mechanisms Of The Nontransition Elements

1st Edition

Author: Donald Matteson
eBook ISBN: 9780323141222
Imprint: Academic Press
Published Date: 28th January 1974
Page Count: 365
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Organometallic Reaction Mechanisms of the Nontransition Elements provides selected significant developments in organometallic reaction mechanisms and outlines a self-consistent set of interpretations of these mechanisms. This book is organized into eight chapters and begins with discussions on bonding in theoretically important types of organometallic compounds and the potential surfaces and their relation to mechanisms. This is followed by significant chapters on electrophilic displacement reactions. Polar 1,2-addition and elimination reactions are covered in a separate chapter. Radical and photochemical reactions are described in the concluding chapters of the book, including the reverse reaction involving incorporation of a free metal and an organic halide into an organometallic compound. Organic chemists and researchers will find this book invaluable.

Table of Contents


Chapter 1 Bonding, Structure, and Potential Energy Surfaces

I. Introduction

II. Carbon-Metal Bonds

III. Three-Center Bonds

IV. Potential Energy Surfaces


Chapter 2 Electrophilic Displacement: NMR Studies of Metal Exchange

I. Introduction

II. Principles of NMR Line Broadening

ΙII. Group III

IV. Group II

V. Lithium

VI. Group IV


Chapter 3 Electrophilic Displacement: Replacements of Metal Cations

I. Transition State Models

II. Mercury(II) Electrophiles

III. Halogen Electrophiles

IV. The Proton as Electrophile or Electrofuge

V. Group IV and V Electrophiles with Grignard and Related Reagents


Chapter 4 Electrophilic Displacement Involving Neighboring Sites

I. Introduction

II. Migrations to Electron-Deficient Oxygen or Nitrogen

III. Migrations to Electron-Deficient Carbon

IV. Migrations of Group VI and VII Anions from Boron to Carbon

V. Migrations of Silicon from Carbon to Oxygen

VI. Cyclopropane Openings and Closings

VII. Electrophilic Displacements with Allylic Rearrangement


Chapter 5 Polar 1, 2-Additions and Eliminations

I. Introduction

II. Carbon-Metal Hyperconjugation

III. Oxymercuration and Oxythallation

IV. Group IV Halide and Related Eliminations

V. Boron Halide Eliminations

VI. Hydroboration

VII. Hydralumination

VIII. Metal Alkyl Additions to Double Bonds


Chapter 6 Carbene Transfer Agents, Carbenes, and Related Topics

I. Introduction

II. Methylene Transfer Reagents

III. Dihalocarbenes

IV. Silenes and Fluoroborene


Chapter 7 Free-Radical and Photochemical Reactions

I. Introduction

II. Principles of Radical Chemistry

III. Replacements of Metal Atoms

IV. Lithium and Sodium Compounds and CIDNP

V. Silyl and Stannyl Radicals

VI. Neighboring Metal Atoms in Carbon Radicals

VII. Photochemistry


Chapter 8 Free Metals and Metal Anions

I. Introduction

II. Mercury Atoms and Mercury Surfaces

III. Thallium and Lead Compounds

IV. Formation of Grignard and Lithium Reagents

V. Organocopper Chemistry

VI. Group IV Anions

VII Notes on Some Topics Not Covered

VIII. Prognosis for Future Research


Author Index

Subject Index


No. of pages:
© Academic Press 1974
28th January 1974
Academic Press
eBook ISBN:

About the Author

Donald Matteson

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