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Photochemical Transformations of Oxadiazepinones and Related Systems'

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The results of our studies on the phototransformations of a few oxadiazepinones are presented. Irradiation of a benzene solution of 2-oxo-7,8-dimethyl-9,9-diphenyt-2,9-dihydro-1,4,5-benzoxadiazepine (1) . gives a mixture of 6,7- dimethyl-2,2- diphenyl-2(H)-1,4,5- bezoxadiazine (4, 8%) and 5,6-dimethyl-2,2-diphenylmethylenebenzo-1,9-dioxole (10, 50%), whereas the irradiation in moist benzene gives 2-hydroxy-4,5-dimethylphenyl diphenylacetate (13). Irradiation of 1 in methanol gives a mixture of 10 (12%), 9,4-dimethylphenol (7, 9%), methyl diphenylacetate (14b, 92%) and 2,9-dimethyl-6-hydroxy-6-methoxy-2-(4,5-dimethyl-2-hydroxyphenylazo)fulvene (17, 14%). Similarly, the irradiation of 2- oxo-9,9- diphenyl-2,9- dihydronaphtho[1,2- b]-1,4, 5- oxadiazepine (18) in benzene gives a mixture of 2-indenylidenenaphtho[1,2-d]-1,9dioxole (22, 4%), indene-9-carboxylic acid (23a, 97%), diphenylacetic acid (14a, 95%) and diphenylacetic anhydride (24, 15%). In contrast, the irradiation of 18 in methanol gives a mixture of 2-methyl diphenylacetate (14b, 61%) and methyl indene-8-carboxylate (23b, 65%). Irradiation of 2,5-dioxo-1,1,4,4-tetraphenylphenanthro[9,10-b] diazetidino[1,2-b]-perhydro-1,4,5-oxadiazepine (25) in benzene gives a mixture of 2,2-diphenylphenanthro[9,10-b]-furan-9(2H)-one (29, 19%) and ,S'-oxo2, 2, 2',2' -tetraphenylphenanthro(9,10-b]-2, 9- dihydrofuran-9-spiro-4'-oxetane (28), whereas the irradiation of 2-oxo-2,5-dihydro-1,4,5-benxoxadiazepine (31) in benzene does not give rise to any product. Irradiation of 31 in methanol, however, gives a mixture of Z-methyl (2-hydrozyphenylhydrazono)glyozalate (34, 12%) and E-methyl (2-hy-droxyphenylhydrazano)glyoxlate (33, 45%). It has been shown that both 33 and 34 undergo interconversion, on irradiation in methanol.

Affiliations: 1: Department of Chemistry Indian Institute of Technology Kanpur 208016, India; 2: Photochemistry Research Unit Regional Research Laboratory (CSIR) Trivandrum 695 019, India, Radiation Laboratory and Department of Chemistry and Biochemistry University of Notre Dame Notre Dame, IN 46556, USA


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