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.
Citation:
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., 32:2 (2022), 271–273
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https://www.mathnet.ru/eng/mendc637
https://www.mathnet.ru/eng/mendc/v32/i2/p271
This publication is cited in the following 3 articles:
V. N. Charushin, E. V. Verbitskiy, O. N. Chupakhin, D. V. Vorobyeva, P. S. Gribanov, S. N. Osipov, A. V. Ivanov, S. V. Martynovskaya, E. F. Sagitova, V. D. Dyachenko, I. V. Dyachenko, S. G. Krivokolylsko, V. V. Dotsenko, A. V. Aksenov, D. A. Aksenov, N. A. Aksenov, A. A. Larin, L. L. Fershtat, V. M. Muzalevskiy, V. G. Nenajdenko, A. V. Gulevskaya, A. F. Pozharskii, E. A. Filatova, K. V. Belyaeva, B. A. Trofimov, I. A. Balova, N. A. Danilkina, A. I. Govdi, A. S. Tikhomirov, A. E. Shchekotikhin, M. S. Novikov, N. V. Rostovskii, A. F. Khlebnikov, Yu. N. Klimochkin, M. V. Leonova, I. M. Tkachenko, V. A.-o. Mamedov, V. L. Mamedova, N. A. Zhukova, V. E. Semenov, O. G. Sinyashin, O. V. Borshchev, Yu. N. Luponosov, S. A. Ponomarenko, A. S. Fisyuk, A. S. Kostyuchenko, V. G. Ilkin, T. V. Beryozkina, V. A. Bakulev, A. S. Gazizov, A. A. Zagidullin, A. A. Karasik, M. E. Kukushkin, E. K. Beloglazkina, N. E. Golantsov, A. A. Festa, L. G. Voskresenskii, V. S. Moshkin, E. M. Buev, V. Ya. Sosnovskikh, I, “The chemistry of heterocycles in the 21st century”, Russian Chem. Reviews, 93:7 (2024), RCR5125
R. Alan Aitken, Progress in Heterocyclic Chemistry, 35, 2023, 333
Peter S. Radulov, Ivan A. Yaremenko, Jennifer Keiser, Alexander O. Terent'ev, “Bridged 1,2,4-Trioxolanes: SnCl4—Catalyzed Synthesis and an In Vitro Study against S. mansoni”, Molecules, 28:13 (2023), 4913
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