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Chalcogenation of 1,4-dichlorobut-2-yne with organic dichalcogenides in the system hydrazine hydrate–KOH

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Abstract

A reaction of organic dichalcogenides R2Y2 (R = Ph, Bn, Pr; Y = S, Se) with 1,4-dichlorobut-2-yne in the system hydrazine hydrate–KOH leads to four principal products: 1,4-bis(organylchalcogenyl)but-2-ynes, 1-organylchalcogenylbut-1-en-3-ynes, 4-organylchalcogenylbut-1-en-3-ynes, and 3(5)-methylpyrazole. The selectivity of the formation of individual products is determined by the ratio of the substrates used and the reaction temperature. A plausible mechanism of chalcogenation considered in the work agrees with the effect of the nature of chalcogene atoms and organic substituents R on stability of intermediates and products. The stabilization of carbanions by α chalcogene-containing groups corresponds to the following order: PhS > PhSe > BnS > BnSe > PrS.

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Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation

    E. P. Levanova, V. S. Vakhrina, V. A. Grabel’nykh, I. B. Rozentsveig, N. V. Russavskaya, A. I. Albanov, L. V. Klyba & N. A. Korchevin

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  1. E. P. Levanova
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  2. V. S. Vakhrina
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  3. V. A. Grabel’nykh
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  4. I. B. Rozentsveig
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  5. N. V. Russavskaya
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  6. A. I. Albanov
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  7. L. V. Klyba
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  8. N. A. Korchevin
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Correspondence to E. P. Levanova.

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Dedicated to Academician of the Russian Academy of Sciences N. S. Zefirov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2083–2089, September, 2015.

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Levanova, E.P., Vakhrina, V.S., Grabel’nykh, V.A. et al. Chalcogenation of 1,4-dichlorobut-2-yne with organic dichalcogenides in the system hydrazine hydrate–KOH. Russ Chem Bull 64, 2083–2089 (2015). https://doi.org/10.1007/s11172-015-1121-1

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  • DOI: https://doi.org/10.1007/s11172-015-1121-1

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