Reactions of organic peroxides. Part XIV. Amino-peroxides from carbonyl compounds, primary amines, and hydrogen peroxide or hydroperoxide

Abstract

The reaction of a number of carbonyl compounds (cyclic and acyclic) with primary amines and hydrogen peroxide gives solid α-hydroperoxy-amines, R¹R²C(NHR³)·O·OH, unstable at room temperature. In such reactions cyclohexanone and hydrogen peroxide can be replaced by 1,1′-dihydroxydicyclohexyl peroxide. Treatment of these α-hydroperoxy-amines with acetic acid–acetic anhydride at room temperature yields the corresponding oxaziridines. Replacement of the hydrogen peroxide by t-butyl hydroperoxide leads to the formation of the correspondingα-t-butylperoxy-amines, R¹R²C(NHR³)·O·OBu^t, compounds which are fairly easily converted into the imines, R¹R²CNR³, by loss of t-butyl hydroperoxide. With acylic ketones only imines, but not t-butylperoxy-amines, could be obtained.