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- Title
Synthesis of unsaturated organochalcogen compounds proceeding from dichloroethenes and organyl dichalcogenides.
- Authors
Levanova, E.; Nikonova, V.; Rosentsveig, I.; Russavskaya, N.; Albanov, A.; Korchevin, N.
- Abstract
Reaction of 1,1- and 1,2-dichloroethenes with PhS, PhSe, BnS, and i-PrS 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.
- Subjects
CHALCOGENIDES synthesis; DICHLOROETHYLENE; ORGANYL groups; NUCLEOPHILES; HYDRAZINE
- Publication
Russian Journal of Organic Chemistry, 2017, Vol 53, Issue 8, p1186
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S107042801708005X