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[2+1] Cycloaddition reaction of α-atlantone with m-CPBA in the light of experimental and MEDT quantum-chemical study

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Chemistry of Heterocyclic Compounds Aims and scope

The two diastereoisomers of 6-(3,4-epoxy-4-methylcyclohexyl)-2-methylhepta-2,5-dien-4-one were synthesized in the [2+1] cycloaddition reaction of α-atlantone, isolated compound from Cedrus atlantica essential oil, with m-chloroperbenzoic acid in CH2Cl2. The chemoselectivity of this cycloaddition reaction has been both experimentally and theoretically studied within the molecular electron density theory. Parr functions and electron localization function analysis of the reagents correctly predicted the experimental chemoselectivity with the most favorable interaction at C3'=C4' bond. These reactions follow a two-stage one-step mechanism.

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Authors and Affiliations

  1. Laboratory of Natural Substances, Faculty of Sciences Semlalia, Cadi Ayyad University, P. O. Box 2390, 40000, Marrakech, Morocco

    Houria Raji, Abdelhak Ouled Aitouna, Redouane Hammal, Ahmed Chekroun & Ahmed Benharref

  2. Molecular Modelling and Spectroscopy Research Team, Faculty of Science, Chouaïb Doukkali University, P. O. Box 20, 24000, El Jadida, Morocco

    Houria Raji, Ali Barhoumi & Abdellah Zeroual

  3. Laboratory of Bioorganic Chemistry, Department of Chemistry, Faculty of Sciences, Chouaïb Doukkali University, P. O. Box 20, 24000, El Jadida, Morocco

    Noureddine Mazoir

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  1. Houria Raji
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  2. Abdelhak Ouled Aitouna
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  3. Ali Barhoumi
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Correspondence to Abdellah Zeroual.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(3), 112–117

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Raji, H., Aitouna, A.O., Barhoumi, A. et al. [2+1] Cycloaddition reaction of α-atlantone with m-CPBA in the light of experimental and MEDT quantum-chemical study. Chem Heterocycl Comp 59, 112–117 (2023). https://doi.org/10.1007/s10593-023-03172-4

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