Studies of Isocyanides. I. The Formation of Urethanes and Ureas from Isocyanides

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Abstract
The reactions of isocyanides with alkyl hypochlorite, N-bromoamides, and hydroxylamine have been investigated. Cyclohexyl and phenyl isocyanides give t-butyl carbamates (urethanes) by the zinc chloride-catalyzed reaction with t-butyl hypochlorite, followed by treatment with water. An analogous reaction with N-bromosuccinimide or N-bromoacetamide in the presence of a small amount of water gives the corresponding acylureas. On treatment with hydroxylamine hydrochloride and zinc chloride, cyclohexyl isocyanide affords N-cyclohexylurea.