Density functional theory study of the regio‐ and stereoselectivity of 1,3-dipolar cycloaddition reactions between 2-ethylthio-4-phenyl-1-azetin and some substituted nitrile oxides

2015 ◽  
Vol 27 (4) ◽  
pp. 1041-1047 ◽  
Author(s):  
Amir Khojastehnezhad ◽  
Hossein Eshghi ◽  
Farid Moeinpour ◽  
Mehdi Bakavoli ◽  
Mohammad Izadyar ◽  
...  
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Density Functional Theory Study ◽  
Functional Theory ◽  
Nitrile Oxides

The 1,3-dipolar cycloaddition of 1H-pyridinium-3-olate and 1-methylpyridinium-3-olate with methyl acrylate: a density functional theory study

Tetrahedron ◽  
2010 ◽  
Vol 66 (47) ◽  
pp. 9187-9193 ◽  
Author(s):  
Lydia Rhyman ◽  
Hassan H. Abdallah ◽  
Sabina Jhaumeer-Laulloo ◽  
Luis R. Domingo ◽  
John A. Joule ◽  
...  
Keyword(s):  
Density Functional Theory ◽  
Methyl Acrylate ◽  
Density Functional ◽  
Dipolar Cycloaddition ◽  
Density Functional Theory Study ◽  
Functional Theory

Mechanism and regioselectivity of 1,3-dipolar cycloaddition reactions of bicyclic monoterpenes with aryl and heteroaryl nitrile oxides: a DFT study

2015 ◽  
Vol 93 (7) ◽  
pp. 749-753 ◽  
Author(s):  
Hossein Eshghi ◽  
Amir Khojastehnezhad ◽  
Farid Moeinpour ◽  
Mehdi Bakavoli
Keyword(s):  
Gas Phase ◽  
Density Functional ◽  
Energy Surface ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Functional Theory ◽  
Nitrile Oxides ◽  
Reactivity Indices ◽  
One Step ◽  
Step Mechanism

The reactivity and regioselectivity of 1,3-dipolar cycloaddition reactions of aryl and heteroaryl nitrile oxides (1a–1c) with bicyclic monoterpenes (R)-(+)-a-pinene (2a) and (S)-(–)-b-pinene (2b) have been investigated by using density functional theory based on reactivity indices and activation energy calculations at the B3LYP/6-31G(d) level of theory in the gas phase. The potential energy surface analyses for both reactions are in agreement with the experimental observations. Moreover, our calculations on the geometries, bond orders, and global electron density transfers at the transition state structures shows that these 1,3- dipolar cycloaddition reactions occur via an asynchronous one-step mechanism.

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