Reaction of cyanotrimethylsilane with oxiranes. Effects of catalysts or mediators on regioselectivity and ambident character

K Imi, N Yanagihara, K Utimoto

Index: Imi, Katsuharu; Yanagihara, Naoto; Utimoto, Kiitiro Journal of Organic Chemistry, 1987 , vol. 52, # 6 p. 1013 - 1016

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Citation Number: 70

Abstract

Reaction of cyanotrimethylsilane with oxiranes under the catalytic action of Lewis acids Pd (CN)*, SnC12, or MeaGa affords 2-trimethylsiloxy isocyanides by regio-and stereoselective attack of isocyanide on the more substituted carbon. The reaction mediated by aluminium alkoxides gives predominantly 3-trimethylsiloxy nitriles by the selective attack of cyanide on the less substituted carbon.