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

Photochemical reactions of azo compounds. IV. Further photochemical cyclodehydrogenations

GM Badger, NC Jamieson and GE Lewis

Australian Journal of Chemistry 18(2) 190 - 198
Published: 1965

Abstract

1,1'-, 1,2'-, 2,2'-Azonaphthalenes, and 2-phenylazonaphthalene are not cyclized photochemically under conditions in which azobenzene is converted into benzo[c]cinnoline and benzidine; but 1-phenylazonaphthalene has been shown to give naphtho[1,2-c]cinnoline, and 4-phenylazobenzene gave 2-phenylbenzo[c]cinnoline. Although 4-styrylazobenzene showed some evidence of cyclization, the reaction was extremely slow and was accompanied by considerable decomposition. 4-Phenylezoazobenzene was cleaved by sulphuric acid, and no cyclized product was obtained. Irradiation of 4,4'-bis(phenylazo)biphenyl gave two cleavage products, and two benzo[c]cinnoline derivatives. Simultaneous reduction and oxidation apparently occurred within the same molecule.

https://doi.org/10.1071/CH9650190

© CSIRO 1965

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