Synthesis of unsaturated organochalcogen compounds proceeding from dichloroethenes and organyl dichalcogenides
- Authors: Levanova E.P.1, Nikonova V.S.1, Rosentsveig I.B.1, Russavskaya N.V.1, Albanov A.I.1, Korchevin N.A.1
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Affiliations:
- Favorskii Irkutsk Institute of Chemistry, Siberian Branch
- Issue: Vol 53, No 8 (2017)
- Pages: 1186-1190
- Section: Article
- URL: https://bakhtiniada.ru/1070-4280/article/view/216685
- DOI: https://doi.org/10.1134/S107042801708005X
- ID: 216685
Cite item
Abstract
Reaction of 1,1- and 1,2-dichloroethenes with Ph2S2, Ph2Se2, Bn2S2, and i-Pr2S2 in a system hydrazine hydrate–KOH proceeds as a sequence of successive transformations: dehydrochlorination of initial dichloroethenes to form chloroacetylene, chlorine substitution for the chalcogen-containing nucleophile (ethynylchalcogenides formation), and the addition of the nucleophilic reagent to the triple bond affording 1,2- dichalcogenylethenes. In reactions with PhS– and PhSe‒ nucleophiles due to the high rate of all stages 1,2-bis (phenylchalcogenyl)ethenes are obtained having mainly the Z-configuration. In reactions with BnS‒ and i-PrS‒ in the IR, NMR and chromato-mass spectra intermediate ethynylchalcogenides were identified, and the final products consisted of a mixture with the prevalence of the Z-isomer.
About the authors
E. P. Levanova
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
V. S. Nikonova
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
I. B. Rosentsveig
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
N. V. Russavskaya
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
A. I. Albanov
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
N. A. Korchevin
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Author for correspondence.
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
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