Simple indoles undergo electrolytic degradation at potentials near +1 V vs the normal hydrogen electrode at a Pb/ PbO2 anode. Oxidation is first order in both current and indole concentration. The reaction is characterized by low CO2 yields and high TOC values, that is, most of the carbon of the starting material remained in the solution after electrolysis. Monomeric, isolable oxidation products were not found even at high conversion. These results are consistent with the intermediacy of hydroxyl radicals, which are produced at the surface of the Pb/PbO2 anode by electrolysis of water, initiating the polymerization of the starting materials to water soluble products with high net current efficiency.