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Photolysis of Acetyl Esters of 2,2'-Dinitrodiphenyl-Carbinols in Protic and Aprotic Solvents

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Irradiation of acetyl esters of 2,2'-dinitrodiphenyl-carbinols (1a-d) in a protic medium like 2-propanol yielded dibenzo[c,f]-[1,2]diazepin-11-one-5-oxides (5a-d) as the major product. Dibenzo[c,f]-[1,2]diazepin-11-one (2a-d), 2,2' -dinitrobenzophenones (3a-d), 2-amino-2' -nitrobenzophenones (4a-d), and N-hydroxyacridones (6a-d) were also formed in varying amounts. Irradiation of 1a-d in an aprotic medium like benzene yielded the above products along with benzisoxazoles (7a-d) also. When triethylamine was used as the solvent the major product obtained was N-hydroxyacridones (6a-d). Plausible mechanisms for the formation of the products are discussed.

Affiliations: 1: Department of Chemistry University of Kerala Trivandrum-695034, Kerala, INDIA


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