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Electrochemical Amination. Selective Functionalization of para- and ortho-Anisidines in Aqueous Sulfuric Acid Solutions

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Abstract

The processes of the electrochemical amination of para- and ortho-anisidines using hydroxylamine and the Ti(IV)/Ti(III) mediator system are studied in aqueous solutions of 4–14 M sulfuric acid. The functionalization of para-anisidine results in the formation of 4-methoxy-1,3- and 4-methoxy-1,2-phenylenediamines with a current efficiency of up to 64.3 and 0.56%, respectively. When ortho-anisidine is aminated, 4-methoxy-1,3-phenylenediamine is the only substitution product; its current efficiency reaches 61%. Under the conditions that favor synthesis of 4-methoxy-1,3-phenylenediamine from anisidines, full conversion of hydroxylamine is observed and the current efficiency of the diamino compound corresponds to the yield per amino radical source.

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Authors and Affiliations

  1. Butlerov Chemical Institute, Kazan (Volga) Federal University, Kazan, 420008, Russia

    Yu. A. Lisitsyn & A. V. Sukhov

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

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Original Russian Text © Yu.A. Lisitsyn, A.V. Sukhov, 2019, published in Elektrokhimiya, 2019, Vol. 55, No. 1, pp. 125–128.

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Lisitsyn, Y.A., Sukhov, A.V. Electrochemical Amination. Selective Functionalization of para- and ortho-Anisidines in Aqueous Sulfuric Acid Solutions. Russ J Electrochem 54, 1294–1297 (2018). https://doi.org/10.1134/S102319351813027X

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  • DOI: https://doi.org/10.1134/S102319351813027X

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