Journal of the American Chemical Society p. 5544 - 5546 (1984)
Update date:2022-08-03
Topics:
Krespan, Carl G.
Van-Catledge, Frederic A.
Smart, Bruce E.
Fluorocarbanions that are produced by the addition of nucleophiles to fluoroolefins can be trapped in many cases with CO2 to form β-substituted polyfluoropropionates directly and in excellent to modest yields.The scope of the reaction encompasses the nucleophiles CN-, N3-, C6H5O-, RS-, (RO)2P(O)-, CF3CH2O- and even Cl-, and the fluoroolefins CF2=CF2, CF2=CFCl, CF2=CFOCF3, and CF2=CFOC3F7.Theoretical calculations of the relative energies for rotamers of four fluorocarbanions support the idea that successful trapping of a fluorocarbanion depends upon formation of a relatively stable conformer in which the incoming nucleophile and unshared electron pair are anti.
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