Quantifying the reactivity of a remarkably long-lived difluorinated enol in acidic methanol via solution kinetics and electronic structure calculations |
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Authors: | Griffith Gerry A Hillier Ian H Percy Jonathan M Roig Ricard Vincent Mark A |
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Affiliation: | Department of Chemistry, University of Leicester, University Road, Leicester LE1 7RH, UK. |
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Abstract: | A simple enol acetal underwent rapid cleavage in acidic solution to generate a difluorinated enol, which was sufficiently long-lived to be characterized by 2D NMR in a protic solvent at ambient temperature. Density functional theory calculations on a model reaction suggest that there are significant differences in protonation transition state timing between the fluorinated and nonfluorinated enols. |
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