REACTIONS OF ORGANIC PEROXIDES .14. AMINO-PEROXIDES FROM CARBONYL COMPOUNDS,PRIMRY AMINES,AND HYDROGEN PEROXIDE OR HYDROPEROXIDE

The reaction of a number of carbonyl compounds (cyclic and acyclic) with primary amines and hydrogen peroxide gives solid α-hydroperoxy-amines. R1R4C(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 corresponding α-t-butylperoxy-amines, R1R2C(NHR 3)·O·OBut, compounds which are fairly easily converted into the imines, R1R2C=NR3, by loss of t-butyl hydroperoxide. With acylic ketones only imines, but not t-butylperoxy-amines, could be obtained.