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

Pyrolysis of Aryl Azides. XIII. Conformational Effects on the Ability of Carbonyl as a Neighbouring Group

LK Dyall, JA Ferguson and TB Jarman

Australian Journal of Chemistry 49(11) 1197 - 1202
Published: 1996

Abstract

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.

https://doi.org/10.1071/CH9961197

© CSIRO 1996

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