Chalcogenation of 1,3-Dichlorobut-2-ene with Organic Dichalcogenides in the System Hydrazine Hydrate–Alkali


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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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