Title : ( Mechanism of 1,3‑ dipolar cycloaddition reactions of indan‑ 1‑ one enamines with aryl nitrile oxide: a DFT analysis )
Authors: Amir Khojastehnezhad , Hossein Eshghi , Farid Moeinpour , Arastou Raoufi ,
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Abstract
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 onestep mechanism with a nonpolar character. Theoretical data are in good agreement with the experimental results.
Keywords
Regioselectivity · [3+2] Cycloaddition · Aryl nitrile oxide · DFT reactivity indices
@article{paperid:1058139,
author = {Amir Khojastehnezhad and Eshghi, Hossein and Farid Moeinpour and Arastou Raoufi},
title = {Mechanism of 1,3‑ dipolar cycloaddition reactions of indan‑ 1‑ one enamines with aryl nitrile oxide: a DFT analysis},
journal = {Journal of the Iranian Chemical Society},
year = {2016},
volume = {13},
number = {9},
month = {May},
issn = {1735-207X},
pages = {1629--1634},
numpages = {5},
keywords = {Regioselectivity · [3+2] Cycloaddition · Aryl nitrile oxide · DFT reactivity indices},
}
%0 Journal Article
%T Mechanism of 1,3‑ dipolar cycloaddition reactions of indan‑ 1‑ one enamines with aryl nitrile oxide: a DFT analysis
%A Amir Khojastehnezhad
%A Eshghi, Hossein
%A Farid Moeinpour
%A Arastou Raoufi
%J Journal of the Iranian Chemical Society
%@ 1735-207X
%D 2016
