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

The reductive halogenation of aromatic azo compounds

BD Wilkinson and DAR Happer

Australian Journal of Chemistry 28(10) 2327 - 2332
Published: 1975

Abstract

The conversion of compounds of the type Ar-N=N-Y into p-X-ArNHNHY by the reaction with hydrogen halides has been re-examined and has been found to be not as general a reaction as expected. The most likely mechanism is one involving nucleophilic addition of halide ion to the aromatic nucleus at the position para to the azo group, this being facilitated by the strong -R character of the -N=N-YH+ substituent. This addition is made essentially irreversible by a series of prototropic shifts resulting in the formation of a stable hydrazo compound.

https://doi.org/10.1071/CH9752327

© CSIRO 1975

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