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

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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%.

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Authors and Affiliations

  1. Butlerov Institute of Chemistry, Kazan Federal University, ul. Kremlevskaya 18, Kazan, Tatarstan, 420008, Russia

    Yu. A. Lisitsyn & A. V. Sukhov

Authors
  1. Yu. A. Lisitsyn
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  2. A. V. Sukhov
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Correspondence to Yu. A. Lisitsyn.

Additional information

Original Russian Text © Yu.A. Lisitsyn, A.V. Sukhov, 2011, published in Elektrokhimiya, 2011, Vol. 47, No. 10, pp. 1262–1267.

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Lisitsyn, Y.A., Sukhov, A.V. Electrochemical amination. Functionalization of anisole in solutions of 4.0–6.0 M H2SO4 and acetic acid. Russ J Electrochem 47, 1180–1185 (2011). https://doi.org/10.1134/S1023193511100120

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  • DOI: https://doi.org/10.1134/S1023193511100120

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