Nitrones and oxaziridines. XXXII. Some reactions of bicyclic 1-pyrroline 1-oxides

Abstract

Oxidation of the bicyclic nitrone (2) with nitric acid gave the nitro diketone (3). Bridgehead hydroxylation was achieved by conversion of the nitrones (1), (2) and (8) into the imino-benzoates (4), (5) and (9) respectively with benzoyl chloride and subsequent base hydrolysis to give the hydroxy-imines (6), (7) and (10) respectively. Photoirradiation of the bicyclic nitrone (2) gave the oxaziridine (14), which on further irradiation gave the fused azetidine (15) and the fused pyrroline (16).