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

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CHEMICAL COMMUNICATIONS
卷 -, 期 31, 页码 3288-3290

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ROYAL SOC CHEMISTRY
DOI: 10.1039/b705034h

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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.

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