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.
- difluorinated enol
- 2D NMR
- fluorinated enol
- organic chemistry
- long-lived difluorinated enol
Percy, J. M., Griffith, G. A., Hillier, I. H., Vincent, M. A., & Roig, R. (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, 8250-8255. https://doi.org/10.1021/jo061450y