Abstract
A mechanism has been proposed for the reaction of 1,3-dichloropropene with dipotassium propane-1,3-bis(dithiolate) 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 first stage of this reaction has been found to be nucleophilic substitution of one chlorine atom of 1,3-dichloropropene linked to the sp3-carbon atom by the sulfur atom of propane-1,3-bis(thiolate) to give the corresponding monosubstitution product. Further transformations of the latter could lead to the formation of six-, seven-, and eight-membered sulfur heterocycles, as well as of a linear structure as a result of reaction of the monosubstitution product with the second 1,3-dichloropropene molecule.
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ACKNOWLEDGMENTS
All calculations were performed on the HPC cluster “Academician V.M. Matrosov” at the Irkutsk Supercomputer Center (http://hpc.icc.ru) and at the Favorsky Irkutsk Institute of Chemistry using the facilities of the Baikal Analytical Center (https://irkinstchem.ru/index.php/ru/struktura-instituta/backp).
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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 7, pp. 973–986 https://doi.org/10.31857/S0514749221070077.
For communication IX, see [1].
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Chirkina, E.A., Krivdin, L.B., Nikonova, V.S. et al. Quantum Chemical Study of Mechanisms of Organic Reactions: X. Reaction of Dipotassium Propane-1,3-bis(thiolate) with 1,3-Dichloropropene in the System Hydrazine Hydrate–KOH. Russ J Org Chem 57, 1073–1083 (2021). https://doi.org/10.1134/S1070428021070071
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DOI: https://doi.org/10.1134/S1070428021070071