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Photoreaction of benzofuroxan
Author(s) -
Hasegawa Minoru,
Takabatake Tohru
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280441
Subject(s) - chemistry , acetonitrile , nitrile , carbazole , photochemistry , mercury vapor lamp , fluorescence , mercury (programming language) , oxide , irradiation , hydrocarbon , inorganic chemistry , organic chemistry , physics , optoelectronics , quantum mechanics , computer science , nuclear physics , programming language
Benzofuroxan 5 , upon irradiation using a high pressure mercury lamp with a Pyrex filter in acetonitrile containing a little water, afforded 1 H ‐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 6 H ‐furazano[4,5‐ 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 .