Issue 31, 2007

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

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?

Article information

Article type
Communication
Submitted
03 Apr 2007
Accepted
14 May 2007
First published
07 Jun 2007

Chem. Commun., 2007, 3288-3290

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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