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Rearrangement of allyl thienyl sulfides to allylthiophenethiols

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It is shown that the rearrangement of allyl 2-thienyl and allyl 3-thienyl sulfides in various solvents at 89–136°C gives the corresponding allylthiophenethiols, which can subsequently undergo transallylation with the starting sulfide and cyclization to thienodihydrothiopyrans and methyldihydrothienothiophenes. The energy of activation of the rearrangement of both isomeric sulfides is 19 kcal/mole. The pKa values of thiophenyl and some thiols of the thiophene series were determined, and it was established that the acidities of the allylthiophenethiols do not have a decisive effect on their ability to undergo cyclization.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 117234, Moscow

    A. V. Anisimov, V. F. Ionova & E. A. Viktorova

Authors
  1. A. V. Anisimov
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  2. V. F. Ionova
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  3. E. A. Viktorova
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 186–189, February, 1978.

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Anisimov, A.V., Ionova, V.F. & Viktorova, E.A. Rearrangement of allyl thienyl sulfides to allylthiophenethiols. Chem Heterocycl Compd 14, 145–148 (1978). https://doi.org/10.1007/BF00945326

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  • DOI: https://doi.org/10.1007/BF00945326

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