Nitrones and oxaziridines. XVIII. Synthesis and photochemistry of 2-Acyl-1-pyrroline 1-Oxides

Abstract

The preparations of 2-benzoyl-5,5-dimethyl-(4a), 2-benzoyl-5,5- dimethyl-4-phenyl-(4b) and 2-formyl-5,5-dimethyl- (13a) 1-pyrroline 1- oxide via the corresponding oximes are described. These oxo nitrones undergo photolysis mainly to 5,5-dimethyl- and 5,5-dimethyl-4-phenyl- pyrrolidin-2-one [(14a) and (14b)].     2-Benzoyl-5,5-dimethyl-1-pyrroline (15) is also a product of irradiation of (4a) and affords the lactam (14a) on reaction with peracid. 2-Benzoyl-5,5-dimethyl-3-oxo-1-pyrroline 1-oxide (9) and its dioxime (8) are also described.