REGIO- AND STEREOSELECTIVITY OF [3+2] CYCLOADDITION REACTIONS BETWEEN (<i>Z</i>)-1-(ANTHRACEN-9-YL)-<i>N</i>-METHYL NITRONE AND ANALOGS OF <i>trans</i>-β-NITROSTYRENE ON THE BASIS OF MEDT COMPUTATIONAL STUDY

Authors

  • Karolina Kula Cracow University of Technology, Institute of Organic Chemistry and Technology, 24 Warszawska St., Cracow PL-31-155, Poland
  • Mikołaj Sadowski Cracow University of Technology, Institute of Organic Chemistry and Technology, 24 Warszawska St., Cracow PL-31-155, Poland

DOI:

https://doi.org/10.1007/7147

Keywords:

nitrone, β-nitrostyrene, cycloaddition reaction, molecular electron density theory, molecular mechanism.

Abstract

The regio- and stereoselectivity of [3+2] cycloaddition reactions of (Z)-1-(anthracen-9-yl)-N-methyl nitrone with analogs of trans-β-nitrostyrene were studied within the molecular electron density theory at the B3LYP/6-31G(d) and MPWB95/6-311G(d,p) theory levels. Analysis of the reactivity indices for presented reactions suggests that nitrone participates as nucleophile, while studied nitroalkenes play a role of electrophiles. According to electron localization function and conceptual density functional theory, kinetic and thermodynamic aspects of processes as well as analysis of all critical structures, the most favored reaction path is the formation of (3RS,4RS,5SR)-3-(anthracen-9-yl)-5-aryl-2-methyl-4-nitroisoxazolidine, independently of simulated solvent.

Author Biographies

Karolina Kula, Cracow University of Technology, Institute of Organic Chemistry and Technology, 24 Warszawska St., Cracow PL-31-155, Poland

Organic synthesis; Cycloaddition Reaction; Regio- and Stereoselectivity; Heterocycle Chemistry; chromatography; Spectroscopy; Quantum-Chemical Calculation; Density Functional Theory; dft; Molecular Electron Desnity Theory; MEDT

Mikołaj Sadowski, Cracow University of Technology, Institute of Organic Chemistry and Technology, 24 Warszawska St., Cracow PL-31-155, Poland

Organic synthesis; Cycloaddition Reaction; Regio- and Stereoselectivity; Heterocycle Chemistry; chromatography; Spectroscopy; Quantum-Chemical Calculation; Density Functional Theory; dft; Molecular Electron Desnity Theory; MEDT

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Published

2023-04-11

Issue

Vol. 59 No. 3 (2023): Cycloaddition reactions: recent progress

Section

Original Papers