Reactions of organic peroxides. Part XI. Amino-peroxides from cyclic ketones
Abstract
It has been found that reaction of various cyclic ketones (cyclopentanone, 2-methyl-, 3-methyl-, 4-methyl- and 3,3,5-trimethylcyclohexanone and cycloheptanone) with hydrogen peroxide and ammonia produces the corresponding 1,1′-peroxydicycloalkylamine and, in some cases, the 1-hydroperoxycycloalkylamine. From cyclododecanone only the hydroperoxy-amine was obtained, whereas isophorone gave, in addition to its epoxide, both 2,3-epoxy-1-hydroperoxy-3,5,5-trimethylcyclohexylamine and 1,1′-peroxybis(2,3-epoxy-3,5,5-trimethylcyclohexyl)amine. The reactions of these peroxides studied included: (i) the formation of unsymmetrical peroxyamines from 1-hydroperoxy-3,3,5-trimethylcyclohexylamine and carbonyl compounds, and (ii) thermal and base-catalysed decomposition of some of the peroxy-amines, both symmetrical and unsymmetrical.