Direct Azidation of Adamantane and Norbornane by Stable Azidoiodinanes

Abstract

Stable azidoiodinanes 1 and 2 react with norbornane, adamantane and 1,3-dimethyladamantane upon heating in the presence of catalytic amounts benzoyl peroxide with the formation of the respective azides 6-8 in moderate yields. In these reactions, reagent 2 can be generated in situ from 2-iodosobenzoic acid and azidotrimethylsilane, and used without isolation.