Quantum chemical study of mechanisms of organic reactions: V. Addition of ethane-1,2-dithiol to 4-hydroxy-4-methylpent-2-ynenitrile
- 作者: Chirkina E.A.1, Mal’kina A.G.1, Ushakov I.A.1, Krivdin L.B.1
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隶属关系:
- Favorskii Irkutsk Institute of Chemistry, Siberian Branch
- 期: 卷 52, 编号 9 (2016)
- 页面: 1267-1276
- 栏目: Article
- URL: https://journals.rcsi.science/1070-4280/article/view/214917
- DOI: https://doi.org/10.1134/S1070428016090037
- ID: 214917
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详细
The mechanism of nucleophilic addition of ethane-1,2-dithiol to 4-hydroxy-4-methylpent-2-ynenitrile has been studied at the DFT B3LYP/6-311++G(d,p) level of theory. The base-catalyzed reaction involves nucleophilic attack by deprotonated ethane-1,2-dithiol on the ß-carbon atom of the nitrile with formation of intermediate Z-vinylic carbanion which undergoes intramolecular cyclization with closure of 1,3-dithiolane ring. Further transformation of 2-[2-(2-hydroxypropan-2-yl)-1,3-dithiolan-2-yl]acetonitrile to 6,6-dimethyl-7-oxo-1,4-dithiaspiro[4.4]nonan-8-imine has also been studied.
作者简介
E. Chirkina
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
编辑信件的主要联系方式.
Email: chirkina_ea@mail.ru
俄罗斯联邦, ul. Favorskogo 1, Irkutsk, 664033
A. Mal’kina
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: chirkina_ea@mail.ru
俄罗斯联邦, ul. Favorskogo 1, Irkutsk, 664033
I. Ushakov
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: chirkina_ea@mail.ru
俄罗斯联邦, ul. Favorskogo 1, Irkutsk, 664033
L. Krivdin
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: chirkina_ea@mail.ru
俄罗斯联邦, ul. Favorskogo 1, Irkutsk, 664033
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