Quantifying the reactivity of a remarkably long-lived difluorinated enol in acidic methanol via solution kinetics and electronic structure calculations.
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.
Griffith
Gerry A
GA
Department of Chemistry, University of Leicester, University Road, Leicester LE1 7RH, UK.
Hillier
Ian H
IH
Percy
Jonathan M
JM
Roig
Ricard
R
Vincent
Mark A
MA