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Reaction of acetylene with organic disulfides

Communication 6. Processes accompanying the reaction

  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    When disulfides are reacted with acetylene, especially under noncatalytic conditions, the vinyl sulfide is formed not only due to vinylation of the thiol, but also by the direct reaction of the disulfide with acetylene.

  2. 2.

    The formation of the 1, 1-bis(alkylthio)ethane occurs as the result of the rearrangement of the vinyl alkyl sulfides, and apparently proceeds reversibly via the transition cyclic complex.

  3. 3.

    The data on the isotopic exchange between vinyl ethyl sulfide and deuteroacetylene indicate the lability of the hydrogen atoms of the vinylthio group, and especially of theβ-trans-protons with respect to theα-proton.

  4. 4.

    In the studied reaction the 1, 2-bis(alkylthio)ethane is formed as the result of the addition of the thiol to the vinyl sulfide.

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Authors and Affiliations

  1. Irkutsk Institute of Organic Chemistry, Siberian Branch of the Academy of Sciences of the USSR, USSR

    N. K. Gusarova, B. A. Trofimov & S. V. Amosova

Authors
  1. N. K. Gusarova
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  2. B. A. Trofimov
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  3. S. V. Amosova
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1092–1097, May, 1972.

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Gusarova, N.K., Trofimov, B.A. & Amosova, S.V. Reaction of acetylene with organic disulfides. Russ Chem Bull 21, 1047–1051 (1972). https://doi.org/10.1007/BF00853766

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  • DOI: https://doi.org/10.1007/BF00853766

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