
%0 Journal Article
%A Lewis, GE 
%A Mayfield, RJ 
%T Photochemical reactions of azo compounds. XII. Dark reaction of <I>cis</I>-azobenzene with acetyl chloride
%J Australian Journal of Chemistry
%D 1967/09/01
%V 20
%N 9
%P 1899-1904
%K 
%R https://doi.org/10.1071/CH9671899
%U https://www.publish.csiro.au/paper/CH9671899 
%X cis-Azobenzene has been shown to react with acetyl chloride in the absence of light to form N,N?-diacetyl-4-chlorohydrazobenzene and N?- acetyl-4-chloro-hydrazobenzene as the principal products; 4- phenylaminoazobenzene and acetanilide are also formed in small amounts. In the course of the reaction a metastable dark blue product arises, and, although this could not be satisfactorily characterized, it was found to yield 4-phenylaminoazobenzene on decomposition in methanolic potassium hydroxide or in acetyl chloride.   The intense blue-purple coloration, which occurs as soon as the reactants are mixed, enables cis-azobenzene to be readily distinguished from its trans isomer.   The nature of the currently reported reaction is discussed in relation to the previously reported photo-induced reaction of trans- azobenzene with acetyl chloride, which yields N,N?-diacetyl-4- chlorohydrazobenzene practically exclusively. 
