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Regio- and stereoselectivity of [3+2] cycloaddition reactions between (Z)-1-(anthracen-9-yl)-N-methyl nitrone and analogs of trans-β-nitrostyrene on the basis of MEDT computational study

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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This work was partially supported by PLGrid Infrastructure.

All calculations reported in this paper were performed on Prometheus supercomputer cluster in the CYFRONET computational center in Cracow.

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

    Karolina Kula & Mikołaj Sadowski

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  1. Karolina Kula
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Correspondence to Karolina Kula.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(3), 138–144

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Kula, K., Sadowski, M. Regio- and stereoselectivity of [3+2] cycloaddition reactions between (Z)-1-(anthracen-9-yl)-N-methyl nitrone and analogs of trans-β-nitrostyrene on the basis of MEDT computational study. Chem Heterocycl Comp 59, 138–144 (2023). https://doi.org/10.1007/s10593-023-03175-1

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