Chiral resolution of R and S 1-phenylethanol on glassy carbon electrodes

The electrochemical oxidation of the chiral alcohol 1-phenyl ethanol (1PE), on carbon electrodes, using TEMPO and an achiral (luitidine) and chiral ((–)-sparteine) base was reinvestigated in order to resolve conflicting reports in literature and to ascertain whether electrochemical chiral resolution is indeed possible with this system. Investigations using electrochemical and FTIR techniques reveal that chiral oxidation occurs due to modification of the working electrode material by the chiral base. This important observation has not been reported previously, in relation to the mechanism discussed here.