Electrochemical study of 4-tert-butylcatechol in the presence of dithiooxamide (rubeanic acid). Electro-organic synthesis of new dithiooxamide derivatives

Electrochemistry provides very versatile means for the electrosynthesis, mechanistic and kinetic studies. Electrosynthesis has become more and more important in organic chemistry due to its following characteristics: unique selectivity because of in situformation of an active species at the interface, inversion in polarity by transfer of electron and variability in product formation by control of potential. The use of water or ionic liquids instead of toxic solvents, room temperature condition, high energy efficiency and using the electrode as electron source instead of toxic reagents are in accord with the principle of green chemistry[1.2]. Dithiooxamide derivatives attract interest as starting compounds for the synthesis of a number of S,N heterocycles [3]. Cyclic voltammogram of 4-tert-buthylcatechol in the presence of dithiooxamide as a nucleophile confirms the reaction of electrochemically generated 4-tert-buthyl-o-benzoquinone with dithiooxamide. The overall reaction mechanism for anodic oxidation of 4-tert-buthylcatechol in the presence of dithiooxamide according to spectroscopy data and cyclic voltammetry and coloumetry results has reported. The work has led to the development of a facile electrochemical method for the synthesis of new and unique dithiooxamide derivative in good yield and purity.