2007•Chemical CommunicationsRequires access
Sulfonyl vs. carbonyl group: which is the more electron-withdrawing?
Isabelle Chataigner, Cécilia Panel, Hélène Gérard, Serge R. Piettre
Open publisher page 112 citations
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.