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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.

the journal of organic chemistry

Quantifying the Reactivity of a Remarkably Long-Lived Difluorinated Enol in Acidic Methanol via Solution Kinetics and Electronic Structure Calculations