Synthesis of unsaturated organochalcogen compounds proceeding from dichloroethenes and organyl dichalcogenides


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Abstract

Reaction of 1,1- and 1,2-dichloroethenes with Ph2S2, Ph2Se2, Bn2S2, and i-Pr2S2 in a system hydrazine hydrate–KOH proceeds as a sequence of successive transformations: dehydrochlorination of initial dichloroethenes to form chloroacetylene, chlorine substitution for the chalcogen-containing nucleophile (ethynylchalcogenides formation), and the addition of the nucleophilic reagent to the triple bond affording 1,2- dichalcogenylethenes. In reactions with PhS and PhSe nucleophiles due to the high rate of all stages 1,2-bis (phenylchalcogenyl)ethenes are obtained having mainly the Z-configuration. In reactions with BnS and i-PrS in the IR, NMR and chromato-mass spectra intermediate ethynylchalcogenides were identified, and the final products consisted of a mixture with the prevalence of the Z-isomer.

About the authors

E. P. Levanova

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

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

I. B. Rosentsveig

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

A. I. Albanov

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

Author for correspondence.
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

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