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Categories: Organic Chemistry >> Synthesis

Silicon-mediated Transformations of Functional Groups

Helmut Vorbrueggen

Hardcover, 366 Pages
First Edition, 2004
ISBN: 3-527-30668-4


In the first work to comprehensively cover this all-important topic, the recognized expert Helmut Vorbrüggen provides both organic and bioorganic chemists with much new and valuable information for preparative synthesis. Its compact form and clear structure make this a long-awaited ready reference.

Editorial Review

The enormous range of silicon-containing functional groups and the variety of applications of silicon-based reagents make authoring an overview challenging. In contrast to their well-known use in protecting groups, applications of silyl functional groups in activation, as leaving groups and as pseudohalides seem to remain in the shadows.

By itself, the number of methods for silylating various functional groups is quite impressive!

The palette of silylating agents available for use in preparing the necessary intermediates is extensive, and they are distinguished by significant differences in reactivity.

Some silicon-based reagents are used as oxidants, and silanes have found applications as reducing agents. A common thread among nearly all of these reactions and reagents is that they allow ready scale-up without difficulty.

The present book provides a broad and comprehensive survey of the reagents, the reactions and their applicable scope. Numerous interesting transformations and practical tips are presented. The author’s own extensive experience is evident in a number of the examples and representative procedures. It is somewhat disappointing that some of the literature references are limited to a few lines and a very busy scheme. On balance, though, "Silicon-mediated Transformations of Functional Groups" is an excellent reference work that highlights a number of alternative transformations to address many important problems in synthesis.


Techniques of Preparative Silylation and Desilylations
Preparation and Properties of Siliconoxy-Leaving Groups
Reactions of Free and Derivatized Carboxylic Acids and Carbonates
Reactions of Aldehydes and Ketones
Reactions of Alcohols, Ethers and Epoxides
Reactions of N-O Systems
Reactions of S-O and Se-O Systems
Cyclizations and Ring Enlargements
Acid- and Base (Fluoride) Catalyzed Eliminations of Trimethylsilanol and Trimethylsilyl Fluoride
Formation of Carbon-Phosphorous Double- and Triple Bonds
Reductions and Oxidations
Dehydration-Activation as well as Silylation of Metalorganic Compounds and of Inorganic Salts
Formation of Polymers