Mechanism of 1,3-dipolar cycloaddition reactions of indan-1-one enamines with aryl nitrile oxide: a DFT analysis

被引：0
|
作者：
Amir Khojastehnezhad
Hossein Eshghi
Farid Moeinpour
Arastou Raoufi
机构：
[1] Islamic Azad University,Young Researchers and Elite Club, Mashhad Branch
[2] Ferdowsi University of Mashhad,Department of Chemistry, Faculty of Sciences
[3] Islamic Azad University,Department of Chemistry, Bandar Abbas Branch
[4] Islamic Azad University,Department of Chemistry, Mashhad Branch
来源：
Journal of the Iranian Chemical Society | 2016年 / 13卷
关键词：
Regioselectivity; [3+2] Cycloaddition; Aryl nitrile oxide; DFT reactivity indices;
D O I：
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学科分类号：
摘要：
The mechanism (regioselectivity) of [3+2] cycloaddition reaction of indan-1-one enamines (1ad–1ce) with aryl nitrile oxide (2) has been investigated by density functional theory-based reactivity indices and activation energy calculations at B3LYP/6-31G(d) level of theory in the gas phase. Thermodynamic and kinetic parameters of the possible 3-regio/4-regio regioisomeric pathways have been determined. In all cases, the 3-regio pathways are more favorable compared to the 4-regio alternatives. Our results show that these cycloadditions follow an asynchronous one-step mechanism with a nonpolar character. Theoretical data are in good agreement with the experimental results.
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页码：1629 / 1634
页数：5
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