Local nucleophile-electrophile interactions in [3+2] cycloaddition reactions between benzonitrile N-oxide and selected conjugated nitroalkenes in the light of MEDT computational study
Karolina Kula, Karolina Zawadzińska
Abstract
The regioselectivity of the [3+2] cycloaddition reactions between benzonitrile N-oxide as three-atom component and two series of para-substituted -nitrostyrene analogues was analysed in the framework of a Molecular Electron Density Theory. All of the considered processes were found to be initiated by the attack of the most nucleophilic oxygen atom in the benzonitrile N-oxide on the most electrophilic carbon atom (C) in the nitroalkenes. This type of interaction favours the formation of 4-nitro-substituted 2 -isoxazolines.
Topics & Concepts
BenzonitrileChemistryNucleophileCycloadditionElectrophileRegioselectivityConjugated systemMedicinal chemistryNitrileOxidePhotochemistryOrganic chemistryCatalysisPolymerOrganic Chemistry Cycloaddition ReactionsChemical Reaction MechanismsFree Radicals and Antioxidants