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Communication | Regular issue | Vol 4, No. 4, 1976, pp.697-703
Published online, 1st January, 1970
DOI: 10.3987/R-1976-04-0697
Photochemical Reactions of 1,2,3,3a,4,5-Hexahydro-N-phenylacetylindol-6-ones

Hideo Iida,* Sakae Aoyagi, and Chihiro Kibayashi

*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


Upon irradiation, 1,2,3,3a,4,5-hexabydro-N-(2-iodo-4,5-dimethoxyphenylacetyl)indol-6-one (2) underwent photocyclization to the indolo[l,7-ab][3]benzazepine derivative (3) and deiodination followed by nonaromatic photo-Fries rearrangement to 1,2,3,3a,4,5-hexahydro-7-(3,4-dimethoxyphenylacetyl)indol-6-one (5), which, upon further irradiation, gave rise to the bibenzyl (11), aldehyde (12), and carboxylic acid (13). The production of these compounds (11 to 13) was accounted for by a mechanism involving an α-cleavage and subsequent ketene formation. The latter process was demonstrated by experiments using several nucleophiles as trapping agents.