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
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.
- Publication:
-
Journal of Molecular Structure
- Pub Date:
- September 2019
- DOI:
- 10.1016/j.molstruc.2019.04.061
- Bibcode:
- 2019JMoSt1192...27W
- Keywords:
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- 3-nitroisoxazoline-2-oxide;
- (3+2) cycloaddition;
- Molecular electron density theory;
- Electron localization function;
- XRD analysis