Nitrones and oxaziridines. X. Photorearrangement of some bicyclic oxaziridines

Abstract

Photochemical irradiation of cis-5-t-butyl-2,2-dimethyl-3-phenyl-6-oxa- 1-aza-bicyclo[3,1,0]hexane (4) afforded 5,5-dimethyl-4- phenylpyrrolidin-2-one (7) and 2,2-di-methyl-3-phenyl-1- pivaloylazetidine (8), which was further hydrolysed by acid to 2-t- butyl-6,6-dimethyl-5-phenyl-5,6-dihydro-4H-1,3-oxazine (9). Photochemical irradiation of 2,2,4,4-tetramethyl-6-oxa-1- azabicyclo[3,1,0]hexane (5) gave only 2,2,4,4-tetramethyl-azetidine-1- carbaldehyde (12).