[2+1] CYCLOADDITION REACTION OF α-ATLANTONE WITH <i>m</i>-CPBA IN THE LIGHT OF EXPERIMENTAL AND MEDT QUANTUM-CHEMICAL STUDY

Authors

  • Houria Raji Laboratory of Natural Substances, Faculty of Sciences Semlalia, Cadi Ayyad University, P. O. Box 2390, 40000 Marrakech, Morocco Molecular Modelling and Spectroscopy Research Team, Faculty of Science, Chouaïb Doukkali University, P. O. Box 20, 24000 El Jadida, Morocco
  • Abdelhak Ouled Aitouna Laboratory of Natural Substances, Faculty of Sciences Semlalia, Cadi Ayyad University, P. O. Box 2390, 40000 Marrakech, Morocco
  • Ali Barhoumi Molecular Modelling and Spectroscopy Research Team, Faculty of Science, Chouaïb Doukkali University, P. O. Box 20, 24000 El Jadida, Morocco
  • Redouane Hammal Laboratory of Natural Substances, Faculty of Sciences Semlalia, Cadi Ayyad University, P. O. Box 2390, 40000 Marrakech, Morocco
  • Ahmed Chekroun Laboratory of Natural Substances, Faculty of Sciences Semlalia, Cadi Ayyad University, P. O. Box 2390, 40000 Marrakech, Morocco
  • Abdellah Zeroual Molecular Modelling and Spectroscopy Research Team, Faculty of Science, Chouaïb Doukkali University, P. O. Box 20, 24000 El Jadida, Morocco
  • Ahmed Benharref Laboratory of Natural Substances, Faculty of Sciences Semlalia, Cadi Ayyad University, P. O. Box 2390, 40000 Marrakech, Morocco
  • Noureddine Mazoir Laboratory of Bioorganic Chemistry, Department of Chemistry, Faculty of Sciences, Chouaïb Doukkali University, P. O. Box 20, 24000 El Jadida, Morocco

DOI:

https://doi.org/10.1007/7235

Keywords:

α-atlantone, [2 1] cycloaddition reaction, electron localization function (ELF), molecular electron density theory (MEDT).

Abstract

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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Published

2023-04-12

Issue

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

Section

Original Papers