Reactions of organic peroxides. Part XVIII. Photo-oxidation of cyclohexylamine and dicyclohexylamine

Abstract

Photo-oxidation of cyclohexylamine in various solvents gave products which included N-cyclohexyl-1-hydro-peroxycyclohexylamine, cyclohexylamine–hydrogen peroxide adduct, N-cyclohexylidenecyclohexylamine, cyclohexanone oxime, 2′-cyclohexylcyclohexanespiro-3′-oxaziridine, amides, and 1-hydroperoxycyclohexylamine; dicyclohexylamine, under similar conditions, generally provided its hydrogen peroxide adduct in addition to N-cyclohexyl-1-hydroperoxycyclohexylamine and N-cyclohexylidenecyclohexylamine. Suggested routes to these products, based on results of control experiments, are given.