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Chemistry of Heterocyclic Compounds

, Volume 25, Issue 10, pp 1113–1117 | Cite as

Mechanism of recyclization of furans to thiophenes and selenophenes under acid catalysis. 1. Kinetic studies of the reaction of 2,5-dialkylfurans with hydrogen sulfide in the presence of hydrochloric acid

  • S. P. Voronin
  • T. I. Gubina
  • I. A. Markushina
  • V. G. Kharchenko
Article

Abstract

The transformation of 2,5-dialkylfurans to thiophenes by reaction with hydrogen sulfide in the presence of hydrochloric acid was studied. The reaction was found to be first order with respect to the furan; the rate of consumption of the furan did not change with increasing length of one of the alkyl substituents. Recyclization in the presence of acid proceeds in two independent directions: through the formation of an intermediate dicarbonyl compound, and by direct conversion of the furan to a thiophene. Kinetic data showed that the reaction occurs mainly by the second route.

Keywords

Hydrogen Sulfide Organic Chemistry Catalysis Hydrochloric Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • S. P. Voronin
    • 1
  • T. I. Gubina
    • 1
  • I. A. Markushina
    • 1
  • V. G. Kharchenko
    • 1
  1. 1.N. G. Chernyshevskii State UniversitySaratov

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