The Electrochemistry of Hydrocarbons in HF / SbF5: Some Mechanistic Conclusions Concerning the Super Acid “Catalyzed” Condensation of Hydrocarbons

The electrochemistries of antimony and simple hydrocarbons were examined in . From cyclic voltammetric data, Sb(V) appears to be a strong oxidizing agent in the super acid media, capable of oxidizing hydrocarbons containing three or more carbon atoms. It is therefore reasonable that the Sb(V) reduction process supplies the energy required for the super acid "catalyzed" condensation of saturated hydrocarbons, confirming suggestions already in the literature. The anodic oxidation of aromatic hydrocarbons was also examined in acidic fluoride media ( and ). It is observed that the oxidation of benzene results in the deposition of electronically conducting polymeric material on the anode. The material has been identified as p‐polyphenylene. The conductivity of the polymer is assumed to result from the formation of a charge‐transfer complex between the partially oxidized polymer and the Lewis acid.