Abstract
Toluene radical anion, generated by dissolving potasssium metal in toluene by the assistance of dicyclohexano-18-crown-6, has been proved to be especially effective for reductive removal of fluorine atom from unactivated alkyl fluorides that resist common reduction conditions. Stereochemical and mechanistic aspects of the present method is discussed. In connection with the preparation of substrates the effect of dipolar aprotic solvents on the nucleophilic fluorination with potassium fluoride/dicyclohexano-18-crown-6 system was also examined, and sulfolane or N, N-dimethylformamide was shown to be a solvent of choice.
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References and Notes
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Ohsawa, T., Oishi, T. (1984). Dissolving Metal Reduction. In: Atwood, J.L., Davies, J.E.D., Osa, T. (eds) Clathrate Compounds, Molecular Inclusion Phenomena, and Cyclodextrins. Advances in Inclusion Science, vol 3. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-5376-5_19
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