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
2
Angarsk State Technical University, Angarsk, Irkutsk oblast, Russia
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Publication type: Journal Article
Publication date: 2018-10-01
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
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.
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Chirkina E. A. et al. 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 // Russian Journal of Organic Chemistry. 2018. Vol. 54. No. 10. pp. 1446-1452.
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Chirkina E. A., Krivdin L. B., Levanova E. P., Korchevin N. A., Rozentsveig I. B. 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 // Russian Journal of Organic Chemistry. 2018. Vol. 54. No. 10. pp. 1446-1452.
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TY - JOUR
DO - 10.1134/s1070428018100020
UR - https://doi.org/10.1134/s1070428018100020
TI - 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
T2 - Russian Journal of Organic Chemistry
AU - Chirkina, E A
AU - Krivdin, L B
AU - Levanova, E P
AU - Korchevin, N A
AU - Rozentsveig, I B
PY - 2018
DA - 2018/10/01
PB - Pleiades Publishing
SP - 1446-1452
IS - 10
VL - 54
SN - 1070-4280
SN - 1608-3393
ER -
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@article{2018_Chirkina,
author = {E A Chirkina and L B Krivdin and E P Levanova and N A Korchevin and I B Rozentsveig},
title = {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},
journal = {Russian Journal of Organic Chemistry},
year = {2018},
volume = {54},
publisher = {Pleiades Publishing},
month = {oct},
url = {https://doi.org/10.1134/s1070428018100020},
number = {10},
pages = {1446--1452},
doi = {10.1134/s1070428018100020}
}
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Chirkina, E. A., et al. “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.” Russian Journal of Organic Chemistry, vol. 54, no. 10, Oct. 2018, pp. 1446-1452. https://doi.org/10.1134/s1070428018100020.