OZONATION OF AMINES .2. COMPETITION BETWEEN AMINE OXIDE FORMATION AND SIDE-CHAIN OXIDATION

The competition between amine oxide formation and side-chain oxidation during ozonation of tri-n-butylamine in several different solvents has been studied, using ozone-nitrogen mixtures. To obtain a better understanding of the side-chain oxidation, 1-di-n-butylamino-2-butanone (XV) was synthesized and ozonized. A preference for attack at the methylene group between the amino and carbonyl groups was observed. The results, including solvent effects, are explained on the basis of competitive fates of an initial amine-ozone adduct. © 1968, American Chemical Society. All rights reserved.