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

Houria Raji, Abdelhak Ouled Aitouna, Ali Barhoumi, Redouane Hammal, Ahmed Chekroun, Abdellah Zeroual, Ahmed Benharref, Noureddine Mazoir
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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.

Keywords


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

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