Abstract
Electron-donor effect of the methyl group in 1,3-dichlorobut-2-ene hampers allylic rearrangement of its primary monochalcogenation products. The use of diphenyl disulfide under harsh conditions (Ph2S2–KOH, 1: 10, 75–80°C) makes it possible to obtain a mixture of six bis(phenylsulfanyl)butenes, 1,1-bis(phenylsulfanyl) but-1-ene being the major component. No bis(phenylselanyl) derivatives have been formed on heating up to 80°C. Dipotassium ethane-1,2-dithiolate reacts with 1,3-dichlorobut-2-ene to give a linear product of chlorine substitution at the sp3-carbon atom in two dichlorobutene molecules and a heterocyclic compound, 2-ethylidene-1,4-dithiane (a mixture of E and Z isomers), whose structure is different from the structure of the product obtained from 1,3-dichloropropene under analogous conditions. Mechanisms have been proposed for the formation of the isolated compounds.
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Original Russian Text © E.P. Levanova, V.S. Nikonova, V.A. Grabel’nykh, N.V. Russavskaya, E.A. Chirkina, A.I. Albanov, I.B. Rozentsveig, N.A. Korchevin, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 12, pp. 1740–1745.
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Levanova, E.P., Nikonova, V.S., Grabel’nykh, V.A. et al. Chalcogenation of 1,3-Dichlorobut-2-ene with Organic Dichalcogenides in the System Hydrazine Hydrate–Alkali. Russ J Org Chem 54, 1754–1759 (2018). https://doi.org/10.1134/S1070428018120023
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DOI: https://doi.org/10.1134/S1070428018120023