Reactions of organic peroxides. Part XIII. Amino-peroxides from carbonyl compounds, ammonia, and hydroperoxides

Abstract

Reaction of cyclohexanone with t-butyl hydroperoxide and ammonia gave 1-t-butylperoxycyclohexylamine which formed normal amine derivatives with phenyl isocyanate, acetyl chloride, benzoyl chloride, ethyl chloroformate, t-butyl hypochlorite, and toluene-p-sulphonyl chloride. Decomposition of the peroxyamine and several of its derivatives by pyrolysis and by treatment with bases was studied. When t-butyl hydroperoxide was replaced by cumene hydroperoxide the product contained the corresponding 1-cumylperoxycyclohexylamine. Treatment of acyclic ketones with t-butyl hydroperoxide and ammonia gave no peroxyamines, whereas evidence was obtained that acyclic aldehydes (acetaldehyde and n-butyraldehyde) gave rise to diperoxyamines.