Issue 31, 2007
From the journal:

Chemical Communications

Sulfonylvs.carbonyl group: which is the more electron-withdrawing?

Isabelle Chataigner,*a   Cécilia Panel,a   Hélène Gérardb  and  Serge R. Piettre*a  

* Corresponding authors

a Laboratoire des Fonctions Azotées et Oxygénées Complexes, Université de Rouen, UMR CNRS 6014, Mont Saint Aignan, France
E-mail: Isabelle.Chataigner@univ-rouen.fr, Serge.Piettre@univ-rouen.fr
Fax: +33 23552 2971
Tel: +33 23552 2410

b Laboratoire de Chimie Théorique, Université Paris VI, 3 rue Galilée, Ivry sur Seine, France

Abstract

Unexpectedly high reactivity of nitrogenated aromatics protected as amides or carbamates, when compared to sulfonamides, can be explained by a decrease of the aromaticity due to a greater ability of the carbon-centered groups to achieve delocalisation of the nitrogen lone pair, resulting in stronger global withdrawing effects.

Graphical abstract: Sulfonyl vs. carbonyl group: which is the more electron-withdrawing?

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Article information

DOI
https://doi.org/10.1039/B705034H
Article type
Communication
Submitted
03 Apr 2007
Accepted
14 May 2007
First published
07 Jun 2007

Chem. Commun., 2007, 3288-3290

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Sulfonyl vs. carbonyl group: which is the more electron-withdrawing?

I. Chataigner, C. Panel, H. Gérard and S. R. Piettre, Chem. Commun., 2007, 3288 DOI: 10.1039/B705034H

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