1,3-Dipolar Cycloaddition of 4-Chlorobenzonitrile Oxide with Some Dipolarophiles: Theoretical Analysis of Regioselectivity
Corresponding Author
Mehdi Bakavoli
Department of Chemistry, School of Sciences, Islamic Azad University, Mashhad Branch, Mashhad, Iran
E-mail: [email protected]Search for more papers by this authorFarid Moeinpour
Department of Chemistry, School of Sciences, Islamic Azad University, Bandar Abbas Branch, Bandar Abbas, Iran
Search for more papers by this authorArezoo Sardashti-Birjandi
Department of Chemistry, School of Sciences, Islamic Azad University, Mashhad Branch, Mashhad, Iran
Search for more papers by this authorAbolghasem Davoodnia
Department of Chemistry, School of Sciences, Islamic Azad University, Mashhad Branch, Mashhad, Iran
Search for more papers by this authorCorresponding Author
Mehdi Bakavoli
Department of Chemistry, School of Sciences, Islamic Azad University, Mashhad Branch, Mashhad, Iran
E-mail: [email protected]Search for more papers by this authorFarid Moeinpour
Department of Chemistry, School of Sciences, Islamic Azad University, Bandar Abbas Branch, Bandar Abbas, Iran
Search for more papers by this authorArezoo Sardashti-Birjandi
Department of Chemistry, School of Sciences, Islamic Azad University, Mashhad Branch, Mashhad, Iran
Search for more papers by this authorAbolghasem Davoodnia
Department of Chemistry, School of Sciences, Islamic Azad University, Mashhad Branch, Mashhad, Iran
Search for more papers by this authorAbstract
Reaction of 4-chlorobenzonitrile oxide (2) which was generated in situ with acrylo nitrile (3), vinyl acetate (4) and allyl bromide (5) as dipolarphile afforded the new cycloadducts 6a, 7a, and 8a compounds, respectively. Reactivity and regiochemistry of these reactions were investigated using activation energy calculations and density functional theory-based reactivity indexes. The theoretical 13C NMR chemical shifts of the cycloadducts which were obtained by gauge-invariant atomic orbital method were comparable with the observed values.
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