Abstract
2H-Perfluorocyclopentanone (1k) and its enol (1e) have been independently synthesized and equilibrated. In carbon tetrachloride, the enol is the only detectable form at equilibrium. In addition to its high relative stability, this enol displays interesting reactivity, including reversible bromination and hydrolysis reactions. Replacing the vinyl fluorine of 1e with hydrogen changes the relative enol stability dramatically as the enol is only present to the extent of 13% in carbon tetrachloride under equilibrating conditions. In Lewis basic solvents, however, the enol is the only detectable form because of its strength as a hydrogen bond donor. Quantum mechanical calculations on both systems suggest that ketone destabilization, but not enol stabilization, by fluorination is responsible for the remarkable relative stability of the enols.
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