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.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1333–1337, October, 1989.
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Voronin, S.P., Gubina, T.I., Markushina, I.A. et al. 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. Chem Heterocycl Compd 25, 1113–1117 (1989). https://doi.org/10.1007/BF00470688
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DOI: https://doi.org/10.1007/BF00470688