T. I. Akimova, O. A. Soldatkina, V. G. Savchenko, A. V. Pilipenko, A. A. Kapustina, “Stereoisomerism in the representative tetracyclic dispiro ozonide derived from (methylene)dicyclohexanone with the 1,5-diketo arrangement”, Mendeleev Commun., 2022, Volume 32, Issue 2,Pages <nobr>271

This article is cited in 3 papers

Communications

Stereoisomerism in the representative tetracyclic dispiro ozonide derived from (methylene)dicyclohexanone with the 1,5-diketo arrangement

T. I. Akimova, O. A. Soldatkina, V. G. Savchenko, A. V. Pilipenko, A. A. Kapustina

Far Eastern Federal University, Vladivostok, Russian Federation

Abstract: The conditions and reasons for the stereoselective transformation of the rac form of 2,2′-(methylene)-dicyclohexanone into the meso- or rac-diastereomer of tetracyclic dispiro ozonide (1,2,4-trioxolane) in the reaction with 30% aqueous H₂O₂ in the presence of acid have been determined. A mechanism for the stereoisomerization of ozonides was proposed, and the stereochemistry of diastereomeric ozonides was established by NMR data.

Keywords: tetracyclic compounds, dispiro compounds, 1,2,4-trioxolanes, Ozonides, Stereoisomerism, 1,5-diketones, hydrogen peroxide.

Language: English

DOI: 10.1016/j.mencom.2022.03.040

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