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


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Resumo

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.

Sobre autores

E. Levanova

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Autor responsável pela correspondência
Email: venk@irioch.irk.ru
Rússia, ul. Favorskogo 1, Irkutsk, 664033

V. Nikonova

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: venk@irioch.irk.ru
Rússia, ul. Favorskogo 1, Irkutsk, 664033

V. Grabel’nykh

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: venk@irioch.irk.ru
Rússia, ul. Favorskogo 1, Irkutsk, 664033

N. Russavskaya

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: venk@irioch.irk.ru
Rússia, ul. Favorskogo 1, Irkutsk, 664033

E. Chirkina

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: venk@irioch.irk.ru
Rússia, ul. Favorskogo 1, Irkutsk, 664033

A. Albanov

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: venk@irioch.irk.ru
Rússia, ul. Favorskogo 1, Irkutsk, 664033

I. Rozentsveig

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: venk@irioch.irk.ru
Rússia, ul. Favorskogo 1, Irkutsk, 664033

N. Korchevin

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: venk@irioch.irk.ru
Rússia, ul. Favorskogo 1, Irkutsk, 664033

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