Journal of Fluorine Chemistry, ( ISI ), Volume (162), No (1), Year (2014-1) , Pages (60-65)

Title : ( Density functional theory study of the regio and stereoselectivity in 1,3-dipolar cycloddition reactions between N-methyl methylenenitrone and fluorinated dipolarophiles )

Authors: Mohammad Rahimizadeh , Hossein Eshghi , Amir khojastehnezhad golmakani , Farid Moeinpour , Mehdi Bakavoli , - - ,

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A DFT study of the reactivity, regio-, and stereoselectivity of 1,3-dipolar cycloaddition of N-methyl- methylenenitrone 1 with (E and Z)-2,4-diethoxy-5-(perfluoroprop-1-en-1-yl)pyrimidine 2E, 2Z and (E and Z)-(perfluoroprop-1-en-1-yl)benzene, 3E, 3Z in the gas phase and in toluene, has been carried out by using density functional theory (DFT)-based reactivity indices and activation energy calculations at B3LYP/6-31G (d) level of theory. Four reactive channels associated with the 5- and 4-regio and endo and exo stereoselective approach modes of the pyrimidine or phenyl group of these fluorinated vinyls relative to nitrone 1 have been explored and characterized. IRC calculations show that these cycloadditions follow an asynchronous concerted mechanism with a low polar character, displaying 5-regioselectivity and it is found that the endo pathway is preferred, therefore the formation of product with 5-regio and endo pathway is dominant. Also, DFT-based reactivity indices clearly predict the experimental regiochemistry.

Keywords

, Regioselectivity, Stereoselectivity, 1, 3-Dipolar cycloaddition, N-Methyl methylenenitrone, Fluorinated vinyls, Density functional
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@article{paperid:1041065,
author = {Rahimizadeh, Mohammad and Eshghi, Hossein and Khojastehnezhad Golmakani, Amir and Farid Moeinpour and Bakavoli, Mehdi and -, -},
title = {Density functional theory study of the regio and stereoselectivity in 1,3-dipolar cycloddition reactions between N-methyl methylenenitrone and fluorinated dipolarophiles},
journal = {Journal of Fluorine Chemistry},
year = {2014},
volume = {162},
number = {1},
month = {January},
issn = {0022-1139},
pages = {60--65},
numpages = {5},
keywords = {Regioselectivity; Stereoselectivity; 1;3-Dipolar cycloaddition; N-Methyl methylenenitrone; Fluorinated vinyls; Density functional calculations.},
}

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%0 Journal Article
%T Density functional theory study of the regio and stereoselectivity in 1,3-dipolar cycloddition reactions between N-methyl methylenenitrone and fluorinated dipolarophiles
%A Rahimizadeh, Mohammad
%A Eshghi, Hossein
%A Khojastehnezhad Golmakani, Amir
%A Farid Moeinpour
%A Bakavoli, Mehdi
%A -, -
%J Journal of Fluorine Chemistry
%@ 0022-1139
%D 2014

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