
%0 Journal Article
%A Dickson, NJ 
%A Dyall, LK 
%T Pyrolysis of aryl azides. V. Characterization of phenylazo, benzoyl and formyl as neighbouring groups
%J Australian Journal of Chemistry
%D 1980/01/01
%V 33
%N 1
%P 91-99
%K 
%R https://doi.org/10.1071/CH9800091
%U https://www.publish.csiro.au/paper/CH9800091 
%X The enhancements of thermolysis rate of azidobenzene produced by ortho phenylazo, benzoyl and substituents are 21180, 70.0 and 22.8 at 393.2 K (decalin solutions). The same ortho substituents produce much smaller enhancements (169, 8.56 and 10.7 respectively) in the pyrolysis rate of 1-azido-2,4-dibromobenzene. These results are interpreted as steric effects on an electro-cyclic thermolysis mechanism, and are not consistent with the alternative pathway of intramolecular 1,3-dipolar addition which continues to be advocated by Hall and Dolan. 
