6533b855fe1ef96bd12b1330

RESEARCH PRODUCT

The structural aspects of the transformation of 3-nitroisoxazoline-2-oxide to 1-aza-2,8-dioxabicyclo[3.3.0]octane derivatives: Experimental and MEDT theoretical study

Krzysztof EjsmontPrzemysław WolińskiAgnieszka Kącka-zychEwa DreslerBłażej DziukAgnieszka ŁApczuk-krygier

subject

Electron densityElectron localization functionChemistryOrganic ChemistryOxide(3+2) cycloadditionCycloadditionElectron localization functionMolecular electron density theoryAnalytical ChemistryStyreneInorganic Chemistrychemistry.chemical_compoundPhysical chemistryAcrylonitrile3-nitroisoxazoline-2-oxideSingle crystalSpectroscopyXRD analysisOctane

description

Abstract Reaction of 3-nitroisoxazoline-2-oxide with monosubstituted ethenes, first time documented fifty years ago, have been reviewed. Structures of phenyl and cyano derivatives of 1-aza-2,8-dioxabicyclo[3.3.0]octane produced in [3 + 2] cycloaddition (32CA) between styrene and acrylonitrile with 3-nitroisoxazoline-2-oxide were determined through single crystal XRD analysis. The molecular mechanism of the title 32CA has been also analyzed within the Molecular Electron Density Theory (MEDT) based on the M06-2X(PCM)/6-311 + G(d,p) calculations.

yearjournalcountryeditionlanguage
2019-09-01Journal of Molecular Structure
https://doi.org/10.1016/j.molstruc.2019.04.061