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A si
mple enol acetal underwent rapid cleavage in acidic solution to generate a difluorinated enol, whichwas sufficiently long-lived to be characterized by 2D NMR in a protic solvent at a
mbient te
mperature.Density functional theory calculations on a
model reaction suggest that there are significant differencesin protonation transition state ti
ming between the fluorinated and nonfluorinated enols.