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1,4-Dichalcogenins: Synthesis from Dichloroethenes and Elemental Chalcogens in a Hydrazine Hydrate–Potassium Hydroxide System

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Abstract

A possibility of the synthesis of 1,4-dichalcogenins by the reaction of vinylidene chloride or 1,2-dichloroethene with elemental chalcogenes in a hydrazine hydrate–KOH system was studied. When vinylidene chloride was used, the maximum yield of 1,4-diselenin was 38%; 1,4-ditellurine was not formed. Diselenin was obtained from 1,2-dichloroethene in 45% yield, while ditellurine was prepared in 21% yield. A plausible mechanism for the formation of dichalcogenin molecules was proposed, which makes it possible to explain the differences in the behavior of 1,1- and 1,2-dichloroethenes in the reaction with potassium telluride. When two chalcogenes were introduced into the reaction, 1,4-dichalcogenins with different chalcogen atoms were obtained with yields of up to 7%.

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Notes

  1. Quantum-chemical calculations were performed by E.A. Chirkina (Angarsk State Technical University) within the electron density functional theory by the B3LYP/6–311++G(d,p) method in accordance with article [12], which considered the dehydrochlorination of vinylidene chloride in the hydrazine hydrate–alkali system.

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ACKNOWLEDGMENTS

The study were carried out using the material and technical base of the Baikal Analytical Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences.

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Authors and Affiliations

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

    V. S. Nikonova, V. A. Grabelnykh, I. N. Bogdanova, N. B. Russavskaya, I. B. Rozentsveig & N. A. Korchevin

  2. Angarsk State Technical University, 665835, Angarsk, Russia

    N. G. Sosnovskaya, N. V. Istomina & N. A. Korchevin

  3. Irkutsk State University, 664003, Irkutsk, Russia

    I. B. Rozentsveig

Authors
  1. V. S. Nikonova
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  2. V. A. Grabelnykh
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  3. I. N. Bogdanova
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  4. N. G. Sosnovskaya
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  6. N. B. Russavskaya
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  7. I. B. Rozentsveig
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  8. N. A. Korchevin
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Corresponding author

Correspondence to V. A. Grabelnykh.

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Additional information

Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 5, pp. 728–734 https://doi.org/10.31857/S0044460X21050097.

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Nikonova, V.S., Grabelnykh, V.A., Bogdanova, I.N. et al. 1,4-Dichalcogenins: Synthesis from Dichloroethenes and Elemental Chalcogens in a Hydrazine Hydrate–Potassium Hydroxide System. Russ J Gen Chem 91, 814–819 (2021). https://doi.org/10.1134/S1070363221050091

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