Polarographic Reduction of Alkyl Halides at a Stationary Lead Electrode

Abstract

The polarographic reduction of some simple alkyl halides at a stationary lead electrode was investigated. Both the iodides and bromides undergo an irreversible one electron reduction with sacrifice of the electrode metal in acetonitrile. The bromide results are compatible with a "backside attack" by the electrode, while the iodides, in keeping with the reverse polarization of the C‐I bond, have a substantially different orientation. In both series the reductions were strongly dependent on the nature of the supporting electrolytecation. The process of metal alkylation and removal are discussed in light of supplementary data from large scale electrosyntheses of organoleads.