Organomercury Compounds in Organic Synthesis

by R.C. Larock

Overview

The field of organometallic chemistry has enjoyed explosive growth in recent years. During this time a rapidly increasing number of metals have found utility in organic synthesis as the corresponding organometallic compounds. The sub­ ject of "Organic Synthesis by Means of Transition Metal Complexes" was reviewed in the first volume of this series of monographs. This volume deals primarily with the appli­ cation of organomercury compounds in organic synthesis (exclusive of solvomercuration-demercuration reactions), but will of necessity involve a number of reactions of other organometallics as well. Organomercurials are among the oldest known organometallics and were perhaps the first to have an entire book devoted to their chemistry, when Whitmore wrote an American Chemical Society monograph on the subject in 1921. Subsequently, two very detailed monographs on the subject have appeared. In 1967 "The Organic Compounds of Mercury", volume 4 in the series "Methods of Elemento­ Organic Chemistry" appeared and this was followed in 1974 by Houben Weyl's full volume, Band XIII/2b, devoted entirely to the organometallic compounds of mercury. These books cover the entire field of organomercury chemistry.

Product Details

ISBN-13:	9783642700064
Publisher:	Springer Berlin Heidelberg
Publication date:	11/17/2011
Series:	Reactivity and Structure: Concepts in Organic Chemistry , #22
Edition description:	Softcover reprint of the original 1st ed. 1985
Pages:	424
Product dimensions:	6.69(w) x 9.61(h) x 0.04(d)

Table of Contents

I. Introduction.- References.- II. Preparation of Organomercury Compounds.- A. Introduction.- B. Direct Mercuration of Organic Halides.- C. Organomagnesium and -Lithium Procedures.- D. Organoboranes.- E. Other Transmetallation Reactions.- F. Mercuration of Carbon Monoxide.- G. Mercury Substitution in Activated C—H Containing Compounds.- H. Mercuration of Cyclopropanes.- I. Mercuration of Alkenes.- J. Mercuration of Alkynes.- K. Mercuration of Aromatic Compounds.- L. Mercury Substitution in Aryldiazonium Salts, Hydrazines, Hydrazones, and Diazo Compounds.- M. Decarboxylation of Mercury Carboxylates.- N. Sulfinate and Sulfonate Elimination Reactions.- References.- III. Hydrogen and Halogen Substitution.- A. Hydrogen Substitution.- B. Halogen Substitution.- References.- IV. Synthesis of Heteroatom-Containing Compounds.- A. Introduction.- B. Oxygen Compounds.- C. Sulfur, Selenium, and Tellurium Compounds.- D. Nitrogen Compounds.- E. Phosphorus Compounds.- F. Silicon Compounds.- G. Conclusion.- References.- V. Dimerization.- References.- VI. Alkylation.- References.- VII. Alkene and Alkyne Addition and Substitution Reactions.- References.- VIII. Carbonylation.- References.- IX. Acylation.- References.- X. Divalent Carbon Transfer Reactions.- A. Introduction.- B. Preparation of the Reagents.- C. Synthesis of Cyclopropanes.- D. Organomercurial Reactivity.- E. Mechanism of Cyclopropane Formation.- F. Synthesis of Cyclopropenones.- G. Ring Expansion Reactions.- H. Reactions with Oxygen, Nitrogen and Sulfur Compounds.- J. Insertion Reactions in Metal—Carbon, Metal—Halide and Metal—Metal Bonds.- References.- Subject Inde.