The Nucleophilicity of Persistent α-Monofluoromethide Anions.

α-Fluorocarbanions are key intermediates in nucleophilic fluoroalkylation reactions. Although frequently discussed, the origin of the fluorine effect on the reactivity of α-fluorinated CH acids has remained largely unexplored. We have now investigated the kinetics of a series of reactions of α-substituted carbanions with reference electrophiles to elucidate the effects of α-F, α-Cl, and α-OMe substituents on the nucleophilic reactivities of carbanions.