Synthesis and diels-alder reactions of e-1-trimethylsilylbuta-1,3-diene

Abstract

A novel synthesis of E-1-trimethylsilylbuta-1,3-diene (1) has been achieved, and its Diels-Alder reactions with maleic anhydride, diethyl maleate, dimethyl fumarate, methyl propiolate, acrolein and acrylonitrile have been investigated. The structures of the products were studied to determine the stereoselectivity and regioselectivity of the reactions of this diene. In all cases with monosubstituted dienophiles the silyldiene 1 afforded the 1,3-disubstituted isomer (meta isomer) as the predominate regioisomer. © 1979.