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Mechanism of recyclization of furans to thiophenes and selenophenes under acid-catalysis conditions. 2. Kinetic investigations of the reaction of 2,5-dialkylfurans with hydrogen sulfide and hydrogen selenide in an anhydrous medium

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The effect of the concentration of the acidic component on the rates of recyclization of 2,5-dialkylfurans to thiophenes and selenophenes was studied. On the basis of the direct correlation of log k on (Ho)I and the isotope effect of the solvent it was established that the reaction proceeds via a mechanism of specific acid catalysis. It was shown that the rates of the reactions with the participation of hydrogen sulfide and hydrogen selenide coincide at equal acidities and temperatures. A scheme for the mechanism of the reaction that includes a step involving the formation of the doubly protonated form of the substrate is proposed.

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Authors and Affiliations

  1. N. G. Chernyshevskii Saratov State University, 410026, Saratov

    S. P. Voronin, T. I. Gubina, S. A. Trushin, I. A. Markushina & V. G. Kharchenko

Authors
  1. S. P. Voronin
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  2. T. I. Gubina
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  3. S. A. Trushin
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  4. I. A. Markushina
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  5. V. G. Kharchenko
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Additional information

See [1] Communication 1.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1458–1462, November, 1989.

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Voronin, S.P., Gubina, T.I., Trushin, S.A. et al. Mechanism of recyclization of furans to thiophenes and selenophenes under acid-catalysis conditions. 2. Kinetic investigations of the reaction of 2,5-dialkylfurans with hydrogen sulfide and hydrogen selenide in an anhydrous medium. Chem Heterocycl Compd 25, 1216–1220 (1989). https://doi.org/10.1007/BF00481514

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  • DOI: https://doi.org/10.1007/BF00481514

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