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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Photochemistry of 2,2'-dinitrodiphenylmethanes: Irradiations in neutral, acidic and alkaline media

CP Joshua and PK Ramdas

Australian Journal of Chemistry 29(4) 865 - 876
Published: 1976

Abstract

Photolysis of 2,2'-dinitrodiphenylmethane (1) in isopropyl alcohol affords dibenzo[c,f][l,2]diazepin-11-one 5-oxide (7) as the major product. Dibenzo[c,f][l,2]diazepin-11-one 5,6-dioxide (6), acridone (8) and 2,2'-dinitrobenzophenone (9) are also formed in the reaction. Irradiation of (1) in ethanolic sulphuric acid on the other hand yields 3-(2'-nitropheny1)-2,l-benzisoxazole (11) as the major product; small amounts of (7), (8) and (9) are also isolated. Photoconversion of (1) in triethylamine and alcoholic triethylamine proceeds very slowly and compounds (7), (8) and (9) only are isolated from the photolysed solution. Some aspects of the mechanism are discussed.

https://doi.org/10.1071/CH9760865

© CSIRO 1976

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