Nitrones. Part III. Photolysis of cyclic nitrones

Abstract

Ultraviolet irradiation of 2-substituted 1-pyrroline 1-oxides yielded corresponding bicyclic oxaziridines. Prolonged irradiation of the 3,3,5-trimethyl-6-oxa-1-azabicyclo[3,1,0]hexane gave an N-acetylazetidine and a pyrroline. Acid hydrolyses of 2,2,5- and 3,3,5-trimethyl-6-oxa-1-azabicyclo[3,1,0]hexane yielded acetonylacetone and 3,3-dimethylpentan-5-al-2-one, respectively. The synthesis of the nitrone 3,3,5-trimethyl-1-pyrroline 1-oxide and its irradiation to form an oxaziridine is described. Prolonged irradiation of the latter yielded a pyrrolidinone.