Sulfonyl vs. carbonyl group: which is the more electron-withdrawing?
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.
Laboratoire des Fonctions Azotées et Oxygénées Complexes, Université de Rouen, UMR CNRS 6014, F-76821, Mont Saint Aignan, France. Isabelle.Chataigner@univ-rouen.fr
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