The Chemistry of N-Substituted Benzotriazoles. Part 22 [1]: Transformations of 1-(Trimethylsilylmethyl)benzotriazoles

Abstract

1 -(Trimethylsilylmethyl)benzotriazole is readily prepared from benzotriazole and chloromethyltrimethylsilane. It undergoes fluoride-catalyzed desilylation with carbonyl compounds and forms an anion that can be alkylated and acylated readily and undergoes Peterson olefination. 1 -(Cyclohexylidenemethyl)benzotriazole is lithiated exclusively at the a carbon atom, and the anion can be cleanly alkylated. 1 -(a-Acylalky1)benzotriazoles are reduced to ketones with zinc and acid. The stability of l-alkenylbenzotriazoles to hydrolysis has been studied.