Quantifying the reactivity of a remarkably long-lived difluorinated enol in acidic methanol via solution kinetics and electronic structure calculations

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Griffith, Gerry A. and Hillier, Ian H. and Percy, Jonathan M. and Roig, Ricard and Vincent, Mark A. (2006) Quantifying the reactivity of a remarkably long-lived difluorinated enol in acidic methanol via solution kinetics and electronic structure calculations. Journal of Organic Chemistry, 71 (21). pp. 8250-8255. ISSN 0022-3263 (https://doi.org/10.1021/jo061450y)

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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.

ORCID iDs

Griffith, Gerry A., Hillier, Ian H., Percy, Jonathan M. ORCID logoORCID: https://orcid.org/0000-0001-8636-2704, Roig, Ricard and Vincent, Mark A.;
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