Quantum-chemical study on the mechanism of formation of geminal hydroxy thiols by reaction of 1,3-dihalopropan-2-ones with hydrogen sulfide

被引：0
|
作者：
V. A. Shagun
L. G. Shagun
I. A. Dorofeev
I. A. Mikhailova
M. G. Voronkov
机构：
[1] Russian Academy of Sciences,Favorskii Irkutsk Institute of Chemistry, Siberian Division
来源：
Russian Journal of Organic Chemistry | 2008年 / 44卷
关键词：
Potential Energy Surface; Hydrogen Sulfide; Halogen Atom; Enol Form; Hydrogen Chloride;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
The reaction mechanism of 1,3-dihalopropan-2-ones with hydrogen sulfide in the presence of hydrogen chloride was studied in terms of the density functional theory. Unlike 1-halopropan-2-ones which give rise to 1-halo-2-sulfanylpropan-2-ols via preliminary enolization, 1,3-dihalopropan-2-ones preferentially undergo direct nucleophilic attack on the carbonyl group by hydrogen sulfide. The potential energy surface for rotational isomerism of 1,3-dihalopropane-2-thiones and 1,3-dihalo-2-sulfanylpropan-2-ols was analyzed, and their most stable rotamers were identified.
引用
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页码：31 / 37
页数：6
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