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 in | Progress in reaction kinetics and mechanism Vol. 40; no. 2 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
London
Sage Publications Ltd
01.04.2015
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Online Access | Get full text |
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Summary: | 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. |
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ISSN: | 1468-6783 1471-406X |
DOI: | 10.3184/146867815X14262620270642 |