Synthesis of unsaturated organochalcogen compounds proceeding from dichloroethenes and organyl dichalcogenides |
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Authors: | E. P. Levanova V. S. Nikonova I. B. Rosentsveig N. V. Russavskaya A. I. Albanov N. A. Korchevin |
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Affiliation: | 1.Favorskii Irkutsk Institute of Chemistry, Siberian Branch,Russian Academy of Sciences,Irkutsk,Russia |
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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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