Electrochemical investigation of the redox properties of some polyfluorinated alkenes. The influence of electrode materials on the shape of polarization curves

The electrochemical reduction of a number of polyfluorovinyl halides RCF=CFX (R = t-C4F9, X = F, Cl, Br; R = Ph, X = F, Cl) has been studied by the cyclic voltammetry technique using various different electrodes. An unusual tendency toward hampering of the reduction was observed on going from X = F to a heavier halogen. Calculations of the energies of the molecular orbitals for these compounds were carried out by the AM1 method. A mechanism of the reduction of polyfluorovinyl halides was suggested on the basis of correlations between the values of the reduction potentials E(Red) the LUMO energies.