Selective Reduction of Saturated Perfluorocarbons

Article abstract of DOI:10.1021/jo00036a019

Perfluorocycloaliphatic compounds are reduced by solutions of the sodium benzophenone radical anion to give perfluorinated and highly fluorinated aromatic compounds.Perfluorocycloalkanes containing tertiary carbon centers are much more reactive than perfluorocyclohexane.Reduction of perfluoroalkanes and perfluorocycloalkanes that contain perfluoroalkyl substituents proceeds easily; however, it appears that overreduction occurs and no organofluorine products are obtained with these substrates.The selectivity and reactivity of several radical anion reducing agents are strongly correlated with the electrochemical behavior of the reducing agents, the perfluoroalkanes, and the observed perfluoroaromatic reduction products.Direct electrochemical reduction of saturated unsubstituted perfluoroalkanes on an analytical scale was observed for the first time in this work.