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Reactions of 1,2-dihaloethanes with chalcogenide anions

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Abstract

Reactions of 1,2-dihaloethanes with chalcogenide anions generated from elemental chalcogens and dimethylchalcogens were performed in the hydrazine hydrate-KOH system. The use of anions Se 2−x and Te 2−x (x = 1−4) resulted in ethylene evolution and chalcogen regeneration (or in increased x value in an anion). Oligomers of Thiokol type formed only in the reaction of the 1,2-dichloroethane with a mixture of potassium disulfide and diselenide. The reductive cleavage of oligomers obtained in the hydrazine hydrate-KOH system followed by methylation led to the formation of 1,2-bis(methylthio)ethane, 1-methylseleno-2-methylthioethane, and 1,2-bis(methylseleno)ethane. The features of substitution with chalcogenide anions in vicinal dihalides are discussed. Mass spectra of compounds obtained were measured and analyzed.

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Authors and Affiliations

  1. Faworsky Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, 664033, Russia

    N. V. Russavskaya, V. A. Grabel’nykh, E. P. Levanova, E. N. Sukhomazova, L. V. Klyba, E. R. Zhanchipova, A. A. Tatarinova, A. V. Elaev, E. N. Deryagina, N. A. Korchevin & B. A. Trofimov

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  1. N. V. Russavskaya
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  2. V. A. Grabel’nykh
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  3. E. P. Levanova
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  4. E. N. Sukhomazova
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  5. L. V. Klyba
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  6. E. R. Zhanchipova
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  7. A. A. Tatarinova
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  8. A. V. Elaev
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  9. E. N. Deryagina
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  10. N. A. Korchevin
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  11. B. A. Trofimov
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Dedicated to Academician of the Russian Academy of Sciences N.S. Zefirov on occasion of his 70th anniversary

Original Russian Text © N.V. Russavskaya, V.A. Grabel’nykh, E.P. Levanova, E.N. Sukhomazova, L.V. Klyba, E.R. Zhanchipova, A.A. Tatarinova, A.V. Elaev, E.N. Deryagina, N.A. Korchevin, B.A. Trofimov, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 5, pp. 672–678.

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Russavskaya, N.V., Grabel’nykh, V.A., Levanova, E.P. et al. Reactions of 1,2-dihaloethanes with chalcogenide anions. Russ J Org Chem 42, 652–658 (2006). https://doi.org/10.1134/S1070428006050022

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  • DOI: https://doi.org/10.1134/S1070428006050022

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