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Quantum Chemical Study of Organic Reactions Mechanisms. XIII. The Reaction of Propargyl Chloride with Potassium 1,2-Ethandithiolate in the System Hydrazine Hydrate–KOH: Heterocyclization Paths
- Authors: Chirkina E.A.1,2, Grabelnykh V.A.1, Korchevin N.A.1,2, Krivdin L.B.1,2, Rosenzweig I.B.1
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Affiliations:
- A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
- Angarsky State Technical University, ul. Chaikovskogo
- Issue: Vol 60, No 10 (2024)
- Pages: 1054-1069
- Section: Articles
- URL: https://modernonco.orscience.ru/0514-7492/article/view/682488
- DOI: https://doi.org/10.31857/S0514749224100083
- EDN: https://elibrary.ru/QLIXDI
- ID: 682488
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Abstract
Quantum chemical modeling of the mechanism of interaction of propargyl chloride with potassium 1,2-ethanedithiolate in the hydrazine hydrate–KOH system was carried out using the combined approach CCSD(T)/6-31+G*//B3LYP/6-311++G**. The elementary stages of the reaction and possible routes for the heterocyclization of the initial intermediates have been found. Under experimental conditions at a reaction temperature of 40-42°C, 6 hours, 2-methyl-5,6-dihydro-1,4-dithiine was obtained with a yield of 25% and 4,7-dithiadecadiine-2,8 with a yield of 24%. At a temperature of –10 ÷ –15°С, cyclic products are not formed.
About the authors
E. A. Chirkina
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences; Angarsky State Technical University, ul. Chaikovskogo
Author for correspondence.
Email: chirkina_ea@mail.ru
ORCID iD: 0000-0002-1733-0685
Russian Federation, Favorskogo, 1, Irkutsk, 664033; ul. Chaikovskogo, 60, Angarsk, 665835
V. A. Grabelnykh
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
Email: chirkina_ea@mail.ru
ORCID iD: 0000-0003-1067-7755
ul. Favorskogo, 1, Irkutsk, 664033
N. A. Korchevin
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences; Angarsky State Technical University, ul. Chaikovskogo
Email: chirkina_ea@mail.ru
Scopus Author ID: 0000-0001-5729-9080
Favorskogo, 1, Irkutsk, 664033; ul. Chaikovskogo, 60, Angarsk, 665835
L. B. Krivdin
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences; Angarsky State Technical University, ul. Chaikovskogo
Email: chirkina_ea@mail.ru
ORCID iD: 0000-0003-2941-1084
Russian Federation, Favorskogo, 1, Irkutsk, 664033; ul. Chaikovskogo, 60, Angarsk, 665835
I. B. Rosenzweig
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
Email: chirkina_ea@mail.ru
ORCID iD: 0000-0001-7817-7816
Russian Federation, , ul. Favorskogo, 1, Irkutsk, 664033
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