Abstract
Benzenesulfenamides and benzeneselenenamides reacted with terminal and internal acetylenes (hex-1-yne, phenylacetylene, hex-3-yne, but-2-yne-1,4-diol, and diphenylacetylene) in the presence of SnCl4 to give the corresponding chloroethenyl sulfides and selenides. From symmetric acetylenes, only E isomers (E)-ArXCR=CClR (X = S, Ar = Ph, 4-ClC6H4; R = Et, Ph, HOCH2; X = Se, Ar = Ph, R = Et) were formed. The reactions of benzenesulfenamide with terminal acetylenes, apart from the corresponding Markownikoff and anti-Markownikoff adducts (PhSCH=CClR and PhSCR=CHCl, R = Bu, Ph) gave ethynyl sulfides PhSC=CR (R = Ph, Bu) and cis/trans-isomeric 1,2-bis(phenylsulfanyl)chloroethenes PhSCR=CClSPh (R = Ph, Bu). The results were interpreted assuming intermediate generation of sulfenyl and selenenyl chlorides via reaction of sulfen-and selenenamides with SnCl4.
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Original Russian Text © A.V. Martynov, N.A. Makhaeva, S.V. Amosova, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 7, pp. 974–978.
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Martynov, A.V., Makhaeva, N.A. & Amosova, S.V. Chlorochalcogenation of acetylenes with benzenesulfen-(or selenen)amides and Tin(IV) chloride. Russ J Org Chem 42, 954–958 (2006). https://doi.org/10.1134/S1070428006070037
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DOI: https://doi.org/10.1134/S1070428006070037