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.
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Original Russian Text © E.P. Levanova, V.S. Nikonova, I.B. Rosentsveig, N.V. Russavskaya, A.I. Albanov, N.A. Korchevin, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 8, pp. 1172–1176.
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Levanova, E.P., Nikonova, V.S., Rosentsveig, I.B. et al. Synthesis of unsaturated organochalcogen compounds proceeding from dichloroethenes and organyl dichalcogenides. Russ J Org Chem 53, 1186–1190 (2017). https://doi.org/10.1134/S107042801708005X
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DOI: https://doi.org/10.1134/S107042801708005X