A simple preparation of trimethylsilylacetonitrile and a novel ring-opening of epoxides with trimethylsilylacetonitrile anion

Abstract

Trimethylsilylacetonitrile (TMSAN) is prepared from halogenoacetonitrile and chlorotrimethylsilane using zinc as a halogen acceptor. TMSAN anion reacts with carbonyl compounds and epoxides to give αβ-unsaturated nitriles (1) and γ-trimethylsiloxynitriles (4) and (6), respectively. The formation of the latter compounds is explained by the intermediacy of (3) which is generated by 1,4-migration of the trimethylsilyl group. Nitriles (4) and (6) are readily transformed to γ-lactone derivatives (5) and (7) with hydrochloric acid in aqueous methanol.