Journal of Organic Chemistry p. 3501 - 3507 (1988)
Update date:2022-09-26
Topics:
Shields, Charles J.
Falvey, Daniel E.
Schuster, Gary B.
Buchardt, Ole
Nielsen, Peter E.
Direct irradiation of 4-<(dimethylamino)carbonyl>phenyl azide (DAA) in an inert solvent with UV light causes ring expansion to an inermediate dehydroazepine and eventual isolation of 4,4'-azobis<<(dimethylamino)carbonyl>benzene> (AZB).The dehydroazepine can be trapped with nucleophilic reagents to give substituted 3H-azepines.The photochemistry of DAA takes a different course when it is sensitized by pyrene, 1-acetamidopyrene (5), or 9-acetamidoacridine (2).Under these conditions, single-electron transfer occurs in competition with energy transfer as evidenced by detection of radical ions in laser transient absorption spectroscopy and by formation of 4-<(dimethylamino)carbonyl>aniline (DAH) as a major product.Energy transfer and electron transfer compete also when the sensitizer and the aryl azide are linked together by a flexible chain of methylene groups.These results have particular significance for the application of such compounds to phtolabeling experiments.
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