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Stereochemistry of the homolytic heterocyclization of alkynes with 1,2-ethanedithol into 1,4-dithianes

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

The homolytic heterocyclization of dialkyl- and diaryl-acetylenes with 1,2-ethanedithiol leads stereoselectively to cis-2,3-disubstituted 1,4-dithianes. The stereochemistry of the reactions is determined by a combination of homolytic trans addition at the triple bond and intramolecular homolytic cis addition at the double bond. The main product of the heterocyclization of dimethyl acetylenedicarboxylate is dimethyl 5,6-dihydro-1,4-dithiin-2,3-dicar-boxylate.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    É. I. Troyanskii, Yu. A. Strelenko, D. V. Demchuk, V. V. Samoshin, A. I. Lutsenko & G. I. Nikishin

Authors
  1. É. I. Troyanskii
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  2. Yu. A. Strelenko
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  3. D. V. Demchuk
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  4. V. V. Samoshin
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  5. A. I. Lutsenko
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  6. G. I. Nikishin
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1841–1849, August, 1991.

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Troyanskii, É.I., Strelenko, Y.A., Demchuk, D.V. et al. Stereochemistry of the homolytic heterocyclization of alkynes with 1,2-ethanedithol into 1,4-dithianes. Russ Chem Bull 40, 1629–1636 (1991). https://doi.org/10.1007/BF01172266

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  • DOI: https://doi.org/10.1007/BF01172266

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