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Issue 3, 2002
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The quest for sulfoquinone imine intermediates in the reaction of sulfanilic acid derivatives with nucleophiles

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Abstract

Data from kinetic and trapping studies suggest that the alkaline hydrolyses of sulfanilyl chloride and of the corresponding N-acetyl derivative follow different reaction pathways. While results for the latter compound are fully consistent with the occurrence of the common associative, SN2 mechanism, the former shows somewhat different features suggesting the incursion of a mechanism of the dissociative type involving a sulfoquinone imine species as a reaction intermediate. The alkaline hydrolyses of the corresponding sulfonyl fluorides and 2,4-dinitrophenyl esters, whose leaving groups are worse than Cl as leaving groups, are all associative.

Graphical abstract: The quest for sulfoquinone imine intermediates in the reaction of sulfanilic acid derivatives with nucleophiles

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Article information


Submitted
12 Sep 2001
Accepted
18 Dec 2001
First published
30 Jan 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 611-614
Article type
Paper

The quest for sulfoquinone imine intermediates in the reaction of sulfanilic acid derivatives with nucleophiles

S. Thea, D. Vigo and G. Cevasco, J. Chem. Soc., Perkin Trans. 2, 2002, 611
DOI: 10.1039/B108215A

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