
%0 Journal Article
%A Dyall, LK 
%A Ferguson, JA 
%A Jarman, TB 
%T Pyrolysis of Aryl Azides. XIII. Conformational Effects on the Ability of Carbonyl as a Neighbouring Group
%J Australian Journal of Chemistry
%D 1996/11/01
%V 49
%N 11
%P 1197-1202
%K 
%R https://doi.org/10.1071/CH9961197
%U https://www.publish.csiro.au/paper/CH9961197 
%X Our previous claim, that locking an ortho carbonyl group into a favourable conformation causes very large increases in the rate of thermolysis of aryl azides , has been reexamined. In 8-azido-5-methoxy-1-tetralone the rate advantage over an azide with a rotatable  ortho acetyl group is estimated to be only 18-fold. Nevertheless, this factor is large enough to invalidate attempts to explain relative neighbouring group abilities on simple electronic effects alone. The very large rate increases we reported previously for 1-azidoacridin-g(10H)-one and 1-azidoanthracene-9,10-dione are partly due to favourable retention of conjugation in the transition state. 
