Electrochemical amination. Functionalization of anisole in solutions of 4.0–6.0 M H2SO4 and acetic acid

Abstract

The electrochemical amination of anisole in 4.0–6.0 M H2SO4 solutions containing CH3COOH and small amounts of water is studied with the use of the Ti(IV)/Ti(III)-NH2OH system. Under these conditions, the products of radical substitution are para- and ortho-anisidines. Their total current efficiency and yield by hydroxylamine are 82.0% at a complete conversion of the source of amine radicals. Owing to the chain mechanism, the electrochemical process is terminated upon consumption of no more than 0.5 electrons per NH2OH molecule. At a small charge passed through the electrolyte, the anisidines current efficiency can exceed 380%.