
%0 Journal Article
%A Badger, GM 
%A Jamieson, NC 
%A Lewis, GE 
%T Photochemical reactions of azo compounds. IV. Further photochemical cyclodehydrogenations
%J Australian Journal of Chemistry
%D 1965/02/01
%V 18
%N 2
%P 190-198
%K 
%R https://doi.org/10.1071/CH9650190
%U https://www.publish.csiro.au/paper/CH9650190 
%X 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. 
