Chemistry Letters

A silyl-functionalized alkyl azide, trimethylsilylmethyl azide; synthesis and cycloaddition reaction to acetylenic dipolarophiles

O Tsuge, S Kanemasa, K Matsuda

Index: Tsuge, Otohiko; Kanemasa, Shuji; Matsuda, Koyo Chemistry Letters, 1983 , p. 1131 - 1134

Full Text: HTML

Citation Number: 12

Abstract

Thermally stable trimethylsilylmethyl azide was first synthesized from the reaction of chloromethyltrimethylsilane with sodium azide. Its use as an α-functionalized synthetic equivalent of methyl azide was demonstrated in the reaction with acetylenic dipolarophiles and the subsequent reaction of the cycloadducts with aldehydes and water in the presence of fluoride ion.