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.
Original language | English |
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Pages (from-to) | 8250-8255 |
Number of pages | 6 |
Journal | Journal of Organic Chemistry |
Volume | 71 |
Issue number | 21 |
DOIs | |
Publication status | Published - 22 Sept 2006 |
Keywords
- difluorinated enol
- 2D NMR
- fluorinated enol
- organic chemistry
- reactivity
- long-lived difluorinated enol