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Amides substituted by one β-sulfonyl group and another β-sulfonyl, β-ester or β-CN group, form very low percentages of the corresponding enols, lo wer than for the β,β-diester and β-cyano, β-ester substituted systems, despite the equal or we aker electron delocalizing ability of the latter groups which help to stabilize the enols more than that of the sulfonyl group. This cannot be attributed to the non-planarity of the enols, since th calculated structures are planar. It is suggested that the sulfonyl-substituted amides are more stabilized than the β-esteror β-cyanosubstituted amides. An amide substituted by β−nonafluorosulfonyl, β−acetyl groups enolizes on the acetyl group, forming a strong, nearly symmetri cal intramolecular hydrogen bond. The use of 600 MHz NMR spectroscopy can extend the range of ob servable enols.

The low KEnol values of β-sulfonyl-substituted amides