Issue 3, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

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

Sergio Thea,*a   Daniele Vigoa  and  Giorgio Cevasco*b  

* Corresponding authors

a Dipartimento di Chimica e Chimica Industriale, Università di Genova, Via Dodecaneso 31, 16146 Genova, Italy
E-mail: Sergio.Thea@chimica.unige.it
Fax: +39 010 36 24337
Tel: +39 010 353 8745

b CNR, Centro di Studio per la Chimica dei Composti Cicloalifatici e Aromatici, Via Dodecaneso 31, 16146 Genova, Italy
E-mail: giocev@chimica.unige.it
Fax: +39 010 36 24337
Tel: +39 010 353 6107

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

DOI
https://doi.org/10.1039/B108215A
Article type
Paper
Submitted
12 Sep 2001
Accepted
18 Dec 2001
First published
30 Jan 2002

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

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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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