Diels-Alder reactions of [alpha]-cyano [alpha],[beta]-unsaturated ketones with 2-methyl-1,3-butadiene: DFT study of mechanism, reactivity and regioselectivity

The mechanism, reactivity and regioselectivity of Diels-Alder cycloaddition reactions of 2-methyl-1,3-butadiene with four dienophiles, (E)-2-benzylidene-3-oxobutanenitrile, (E)-2-(furan-2-ylmethylene)-3-oxopentanenitrile, (E)-2-benzylidene-4,4-dimethyl-3-oxopentanenitrile, and (E)-2-benzoyl-3-(furan...

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Published inProgress in reaction kinetics and mechanism Vol. 40; no. 2
Main Authors Nouri, Azita, Zahedi, Ehsan, Jafari, Fateme Joneydi, Nouri, Arezu
Format Journal Article
LanguageEnglish
Published London Sage Publications Ltd 01.04.2015
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Abstract The mechanism, reactivity and regioselectivity of Diels-Alder cycloaddition reactions of 2-methyl-1,3-butadiene with four dienophiles, (E)-2-benzylidene-3-oxobutanenitrile, (E)-2-(furan-2-ylmethylene)-3-oxopentanenitrile, (E)-2-benzylidene-4,4-dimethyl-3-oxopentanenitrile, and (E)-2-benzoyl-3-(furan-2-yl) acrylonitrile, have been studied by means of several theoretical approaches. The regioselectivity of these reactions has been confirmed by their activation energies, the Gazquez-Mendez rule, Houk's rule and global descriptors of the products. All the studied reactions have normal electron demand character and a polar nature. All calculations were done at the DFT-B3LYP/6-31G(d) level of theory.
AbstractList The mechanism, reactivity and regioselectivity of Diels-Alder cycloaddition reactions of 2-methyl-1,3-butadiene with four dienophiles, (E)-2-benzylidene-3-oxobutanenitrile, (E)-2-(furan-2-ylmethylene)-3-oxopentanenitrile, (E)-2-benzylidene-4,4-dimethyl-3-oxopentanenitrile, and (E)-2-benzoyl-3-(furan-2-yl) acrylonitrile, have been studied by means of several theoretical approaches. The regioselectivity of these reactions has been confirmed by their activation energies, the Gazquez-Mendez rule, Houk's rule and global descriptors of the products. All the studied reactions have normal electron demand character and a polar nature. All calculations were done at the DFT-B3LYP/6-31G(d) level of theory.
Author Zahedi, Ehsan
Nouri, Arezu
Nouri, Azita
Jafari, Fateme Joneydi
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