Quantum Chemical Study of Mechanisms of Organic Reactions: VII. Reaction of Ethane-1,2-dithiol with 1,3-Dichloropropene in the System Hydrazine Hydrate–KOH


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Abstract

A mechanism has been proposed for the reaction of 1,3-dichloropropene with ethane-1,2-dithiol in the system hydrazine hydrate–potassium hydroxide on the basis of DFT quantum chemical calculations [B3LYP/6-311++G(d,p)]. The proposed mechanism involves several consecutive steps, in particular nucleophilic substitution of chlorine at the sp3-hybridized carbon atom by sulfur, prototropic allylic rearrangement of the monosubstitution product with double bond migration toward the sulfur atom, dithiolane ring closure via nucleophilic attack of the second thiolate group on the carbon atom in the γ-position with respect to the second chlorine atom, and prototropic allylic rearrangement of 2-vinyl-1,3-dithiolane to more stable 2-ethylidene-1,3-dithiolane.

About the authors

E. A. Chirkina

Favorskii Irkutsk Institute of Chemistry, Siberian Branch; Angarsk State Technical University

Author for correspondence.
Email: chirkina_ea@mail.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033; ul. Chaikovskogo 60, Angarsk, Irkutsk oblast, 665835

L. B. Krivdin

Favorskii Irkutsk Institute of Chemistry, Siberian Branch; Angarsk State Technical University

Email: chirkina_ea@mail.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033; ul. Chaikovskogo 60, Angarsk, Irkutsk oblast, 665835

E. P. Levanova

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

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

N. A. Korchevin

Favorskii Irkutsk Institute of Chemistry, Siberian Branch; Angarsk State Technical University

Email: chirkina_ea@mail.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033; ul. Chaikovskogo 60, Angarsk, Irkutsk oblast, 665835

I. B. Rozentsveig

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

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

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