Photolysis of Acylsilanes in Cyclohexane and Other Solvents

Abstract

Whereas photolysis of acylsilanes in carbon tetrachloride has been shown to generate silyl radicals which yield chlorosilanes exclusively, and photolyses in alcohols yield siloxycarbenes which yield "mixed acetal" insertion products, it is shown that photolysis of acylsilanes in non-polar, non-halogenated solvents such as cyclohexane give complex mixtures of products which result primarily from the attack of silyl radicals on the carbonyl oxygen of an acylsilane, followed by conventional disproportionation or recombination reactions. Under some circumstances silyl radicals add to carbon–carbon double bonds. The structures of the products formed and the mechanism of their formation are described.