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

被引：0

作者：

Khojastehnezhad, Amir ^{[1
]}

Eshghi, Hossein ^{[2
]}

Moeinpour, Farid ^{[3
]}

Raoufi, Arastou ^{[4
]}

机构：

[1] Islamic Azad Univ, Mashhad Branch, Young Researchers & Elite Club, Mashhad, Iran

[2] Ferdowsi Univ Mashhad, Dept Chem, Fac Sci, Mashhad, Iran

[3] Islamic Azad Univ, Bandar Abbas Branch, Dept Chem, Bandar Abbas 7915893144, Iran

[4] Islamic Azad Univ, Mashhad Branch, Dept Chem, Mashhad, Iran

来源：

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY | 2016年 / 13卷 / 09期

关键词：

Regioselectivity; 3+2] Cycloaddition; Aryl nitrile oxide; DFT reactivity indices; DENSITY-FUNCTIONAL THEORY; THEORETICAL-ANALYSIS; REGIOSELECTIVITY; ISOXAZOLINES; REACTIVITY; 1,2,4-OXADIAZOLES; DIPOLAROPHILES; NITRILIMINES; OPTIMIZATION; REPLACEMENTS;

D O I：

10.1007/s13738-016-0879-x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

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.

引用

页码：1629 / 1634

页数：6

共 38 条

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