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The Nucleophilicity of Persistent α‐Monofluoromethide Anions |
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| Authors: | Dr Zhe Zhang Dr Ángel Puente Dr Fang Wang Dr Martin Rahm Yuncai Mei Prof?Dr Herbert Mayr Prof?Dr G K Surya Prakash |
| Institution: | 1. Loker Hydrocarbon Research Institute, Department of Chemistry, University of Southern California, Los Angeles, CA, 90089-1661 USA;2. Department Chemie, Ludwig-Maximilians-Universit?t München, Butenandtstrasse 5–13 (Haus F), 81377 München, Germany;3. Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, NY, 14853-1301 USA |
| Abstract: | 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. |
| Keywords: | carbanions fluorine effect fluoromethylation linear free energy relationship nucleophilicity |