Title : ( The origin of regio- and stereoselectivity in 1,3-dipolar cycloaddition of nitrile oxides with C1-substituted 7- oxabenzonorbornadienes, A DFT study )
Authors: javad tajabadi , Mehdi Bakavoli , Mostafa Gholizadeh , Hossein Eshghi , Mohammad Izadyar ,
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Abstract
In this computational study, density functional theory (DFT) calculations were performed in order to achieve a deep understanding of the regio- and stereoselectivity of 1,3-dipolar cycloadditions (1,3-DC) of C1-substituted 7-oxabenzonorbornadienes (OBNDs) (2a-2d) with acetonitrile oxide (1a) and benzonitrile oxide (1b). The potential energy surface analysis, Wiberg bond orders (BOs) and global electron density transfer (GEDT) at the transition states (TSs) show that these cycloadditions take place through a low asynchronous one-step mechanism with none polar character. Mechanism studies display these reactions are exo-stereoselective and anti-regioselective (3X) and classified as (pseudodiradical) prtype 1,3-DC reactions. These results are in excellent agreement with the experimental observations. Distortion-interaction model has been used successfully for understanding of regio- and stereoselectivity in these reactions.
Keywords
, regioselectivity, stereoselectivity, 1, 3-dipolar cycloaddition, 7-oxabenzonorbornadienes, nitrile oxides, distortioninteraction model.
@article{paperid:1047631,
author = {Tajabadi, Javad and Bakavoli, Mehdi and Gholizadeh, Mostafa and Eshghi, Hossein and Izadyar, Mohammad},
title = {The origin of regio- and stereoselectivity in 1,3-dipolar cycloaddition of nitrile oxides with C1-substituted 7- oxabenzonorbornadienes, A DFT study},
journal = {RSC Advances},
year = {2015},
volume = {5},
number = {2},
month = {May},
issn = {2046-2069},
pages = {38489--38498},
numpages = {9},
keywords = {regioselectivity; stereoselectivity; 1;3-dipolar cycloaddition; 7-oxabenzonorbornadienes; nitrile oxides; distortioninteraction model.},
}
%0 Journal Article
%T The origin of regio- and stereoselectivity in 1,3-dipolar cycloaddition of nitrile oxides with C1-substituted 7- oxabenzonorbornadienes, A DFT study
%A Tajabadi, Javad
%A Bakavoli, Mehdi
%A Gholizadeh, Mostafa
%A Eshghi, Hossein
%A Izadyar, Mohammad
%J RSC Advances
%@ 2046-2069
%D 2015
