Electrochemical and Spectroscopic Studies of 3,5-Di-tert-butyl-2-aminophenol and of Electrosynthesized 3,5-Di-tert-butyl-2-iminocyclohexa-3,5-dienone in Aprotic Solvents

Article abstract of DOI:10.1021/jo00193a024

In acetonitrile 3,5-di-tert-butyl-2-iminocyclohexa-3,5-dienone (DTBQI) is the major product from the controlled-potential electrooxidation of 3,5-di-tert-butyl-2-aminophenol (DTBAPH2).The same product results from the chemical oxidation of DTBAPH2 by PbO2.The redox chemistry for DTBAPH2, DTBQI, and o-aminophenol in dimethyl sulfoxide and acetonitrile has been studied with cyclic voltammetry and controlled-potential electrolysis, and the products and intermediates have been characterized by 1H and 13C NMR, ESR, IR, and UV-vis spectroscopy.Addition of strong base (OH^-) to DTBQI causes it to be reduced to a product with the characteris tics of DTBAPH^-.Redox reaction mechanisms are proposed for the electrochemical oxidation of DTBAPH^- to DTBQI and for the latter's reduction.