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
2021
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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