Synthetic Applications of Chloromethyltrimethylsilane

The use of chloromethyltrimethylsilane and its derivatives to accomplish a wide range of synthetic transformations in organic chemistry is discussed. Organometallics, (Grignard and lithium reagents) derived from it, as well as key intermediates such as 3-chloro-2-trimethylsiloxypropene, ethyl trimethylsilylacetate, 2-trimethylsilylmethyl-1,3-butadiene, trimethylsilyldiazomethane, and a series of 2-(trimethylsilyl)-ethyl-based derivatizing reagents, play a major role in its applications. These compounds and other derivatives are important reagents for the preparation of such diverse products as unsaturated compounds, isoprenylated compounds, Diels-Alder adducts, ylids, and heterocyclic compounds. 1. Introduction 2. Reactions of Trimethylsilylmethylmagnesium Chloride 3. Lithium Derivatives 4. Trimethylsilyldiazomethane 5. Trimethylsilylmethyl Derivatives 6. Ylid Chemistry 7. 2-Alkynyl-trimethylsilanes