Studies of Isocyanide. II. The Reaction of Isocyanide with Some Radical Sources

Abstract

Abstract The reactions of cyclohexyl isocyanide with some radical sources, such as perbenzoic acid, benzoyl peroxide, t-butyl perbenzoate, N-nitrosoacetanilide, potassium phenylazoformate and di-t-butyl peroxide, have been studied. The isocyanide does not contribute kinetically to the mechanism of the decomposition of benzoyl peroxide, but the lone pair electrons existing on the carbon atom of isocyanide react very easily with free radicals, especially with acyloxy radicals. In the reaction with benzoyl peroxide, t-butyl perbenzoate or the N-nitrosoacetanilide acyloxy radical chiefly contributes to the reaction. With potassium phenylazoformate, the phenyl radical is the main reacting species. However, in the case of perbenzoic acid, the reaction is heterolytic, and the main product is cyclohexyl isocyanate.