| Abstract: | Benzofuroxan 5 , upon irradiation using a high pressure mercury lamp with a Pyrex filter in acetonitrile containing a little water, afforded 1H-azepine-2,7-dione 6 . The initial stage of this reaction would be formation of a highly reactive intermediate possessing two nitrile oxide functions. On the other hand, when compound 5 was irradiated using a low pressure mercury lamp in acetonitrile containing a little water, it afforded 6H-furazano4,5-c]carbazole 3-oxide 11 and compound 6 . The structure of compound 11 was determined by an X-ray structural analysis. In the presence of an aromatic hydrocarbon, the formation of compound 11 was decreased and that of compound 6 was increased. Mechanistic studies on the photoreaction suggest that the photosensitized formation of compound 6 with the aromatic hydrocarbon may be carried out by the reabsorption of the fluorescence of it near 365 nm and the presence of it may quench the formation of compound 11 . |
