Peracid oxidation of 1-pyrroline 1-oxides

Abstract

Peracid oxidation of twelve 1-pyrroline 1-oxides (a class of cyclic nitrones) has been carried out.  Those compounds without a substituent in position 2 yielded the corresponding hydroxamic acids. 2-Phenyl-substituted 1-pyrroline 1-oxides gave nitro ketones, whereas 2-alkyl substituted 1-pyrroline 1-oxides gave nitroso ketones (as dimers) or nitro ketones. 2,4,4-Trimethyl-1-pyrroline 1-oxide gave an abnormal oxidation product, 2,4,4-trimethyl-1-pyrrolin-5-ol 1-oxide. Possible mechanisms of these reactions are discussed.