Chalcogenation of 1,3-Dichlorobut-2-ene with Organic Dichalcogenides in the System Hydrazine Hydrate–Alkali
- Authors: Levanova E.P.1, Nikonova V.S.1, Grabel’nykh V.A.1, Russavskaya N.V.1, Chirkina E.A.1, Albanov A.I.1, Rozentsveig I.B.1, Korchevin N.A.1
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Affiliations:
- Favorskii Irkutsk Institute of Chemistry, Siberian Branch
- Issue: Vol 54, No 12 (2018)
- Pages: 1754-1759
- Section: Article
- URL: https://journal-vniispk.ru/1070-4280/article/view/219483
- DOI: https://doi.org/10.1134/S1070428018120023
- ID: 219483
Cite item
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.
About the authors
E. P. Levanova
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Author for correspondence.
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
V. S. Nikonova
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
V. A. Grabel’nykh
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
N. V. Russavskaya
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
E. A. Chirkina
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
A. I. Albanov
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
I. B. Rozentsveig
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
N. A. Korchevin
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
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