Journal of the Iranian Chemical Society, ( ISI ), Volume (13), No (9), Year (2016-5) , Pages (1629-1634)

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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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
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@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},
}

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%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

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