Journal of the Chemical Society. Perkin transactions II p. 691 - 696 (1988)
Update date:2022-08-02
Topics:
Bamfield, Peter
Greenwood, David
Lotey, Harvinder
Stirling, Charles J. M.
The mechanism of conversion of o-nitrothiophenols into o-aminobenzenesulphonic acids in aqueous dioxane has been investigated with particular reference to evidence for the rate-determining formation of a cyclic intermediate.This intermediate is susceptible to interception by both external and internal nucleophilic functions, and the sulphonic acid is shown by isotope labelling experiments to take two oxygen atoms from H2(18)O in the reaction mixture, under conditons in which neither starting materials nor products exchange with H2(18)O.A tentative pathway is advanced.
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