Quantum chemical studies of mechanisms of organic reactions: VI. Reaction of ethane-1,2-dithiol with vinylidene chloride


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Abstract

A theoretical mechanism has been proposed for the reaction of vinylidene chloride with ethane-1,2-dithiol in the system hydrazine hydrate–potassium hydroxide on the basis of DFT quantum chemical calculations at the B3LYP/6-311++G(d,p) level of theory. The reaction includes two consecutive stages: dehydrochlorination of vinylidene chloride to chloroacetylene and nucleophilic addition of one thiol group of ethane-1,2-dithiol to the β-carbon atom of chloroacetylene, followed by closure of 2,3-dihydro-1,4-dithiine ring via nucleophilic substitution of chlorine by sulfur atom of the second thiol group.

About the authors

E. A. Chirkina

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Author for correspondence.
Email: chirkina_ea@mail.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

E. P. Levanova

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: chirkina_ea@mail.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

L. B. Krivdin

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: chirkina_ea@mail.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

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