Nitrones and Oxaziridines, XXIII. Photorearrangement of 2-Cyano-1-pyrroline 1-Oxides

Abstract

2-Cyano-1-pyrroline 1-oxides undergo photorearrangement at 254 nm in benzene to afford cyanoformylazetidines [(azetidinyl)oxoacetonitriles] via the related oxaziridines. The cyanoformylazetidines can be hydrated by means of manganese(IV) oxide to the crystalline oxamoyl azetidines. Several previously unreported 2-cyano nitrones have been prepared by dehydration of the related 2-hydroxyimino nitrones with 2,4-dinitrofluorobenzene followed by triethylamine. Several of the intermediate oxime ethers have been isolated and characterized.