Preparation of a Trans α,β-Epoxysilane by Selective Pyrolysis

Abstract

α,β-Epoxysilanes have been shown to be useful synthetic intermediates² for the preparation of carbonyl compounds³ and stereoisomerically-pure olefins⁴ and heteroatom-substituted olefins⁵ (vinyl bromides,⁵ enol acetates,⁵ enol ethers,⁵ enamides,⁵ and vinyl mesylates⁶). In many of their reactions, α,β-epoxysilanes serve as stereospecific vinyl cation equivalents;⁴–6 therefore methods to prepare stereoisomerically-pure α,β-epoxysilanes are of considerable importance. Although other methods for preparing α,β-epoxysilanes have recently been developed,⁷ the only general method for preparing stereoisomerically-pure α,β-epoxysilanes is epoxidation of the corresponding vinylsilanes.