Tetrahedron

Substituent effects in keto-enol tautomerism. Part 3. 1 influence of substitution on the equilibrium composition of of β-dicarbonyl compounds

M Bassetti, G Cerichelli, B Floris

Index: Bassetti, M.; Cerichelli, G.; Floris, B. Tetrahedron, 1988 , vol. 44, # 10 p. 2997 - 3004

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Citation Number: 53

Abstract

The enol content and equilibrium free energies for the keto-enol tautomerism have been determined for a series of 1, 3-diketones, at 40° C, in deuterochloroform and dimethylsulfoxide-d6 (DMSO), by1H nmr. Compounds containing methyl, phenyl, t-butyl, 2- thienyl, trifluoromethyl and ethoxy groups have been examined. The equilibrium free energies in DMSO are characterized by a linear additivity effect, and substituent ...