Reactions of organic peroxides. Part XVI. Amino-peroxides from autoxidation of imines

Abstract

A number of imines [graphic omitted]N·CHR¹ R²(R¹= aryl; R²= methyl or aryl), on oxygenation at –15 to –20°(u.v.) or at room temperature (R¹ and R²= aryl), gave the corresponding cyclic amino-peroxides [graphic omitted]. Thermal or base-catalysed decomposition of these amino-peroxides provided the corresponding ketones, R¹COR², caprolactam (low yield), and a number of by-products, some of which have been characterised. On the other hand the imines Ph₂CH·CH:NR (R = C₆H₁₁ or CHPh₂) gave rather unstable hydroperoxides, Ph₂C(O·OH)·CH:NR, on oxygenation.