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Transformations of 3-(Bromomethyl)-5,7-dimethyl-2-oxaadamantan-1-ol in Sulfuric Acid

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Abstract

Reactions of 3-(bromomethyl)-5,7-dimethyl-2-oxaadamantan-1-ol with 96% sulfuric acid in the absence and in the presence of nucleophiles have been studied. These reactions involve a series of skeletal transformations and open the way to difficultly accessible 1,2,3-trisubstituted adamantanes. The structure of the synthesized compounds was studied by 2D NMR spectroscopy and X-ray analysis. The products can be used as starting materials for the synthesis of new cage heterocycles with potential biological activity.

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ACKNOWLEDGMENTS

This study was performed using the facilities of the “Investigation of Physicochemical Properties of Compounds and Materials” joint center at the Samara State Technical University. The Stoe STADI VARI Pilatus100K diffrac­tometer used for the X-ray diffraction study of compound 4 was purchased according to the program for the development of Moscow State University.

Funding

The syntheses were financially supported by the Russian Science Foundation (project no. 20-73-00250). Spectral studies were performed under financial support by the Ministry of Science and Higher Education of the Russian Federation (project no. FSSE-2023-0003) in the framework of state assignment to Samara State Technical University.

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Authors and Affiliations

  1. Samara State Technical University, 443100, Samara, Russia

    E. A. Ivleva, E. V. Simatova, M. S. Zaborskaya, M. S. Kazachkova & Yu. N. Klimochkin

  2. Faculty of Chemistry, Moscow State University, 119991, Moscow, Russia

    V. B. Rybakov

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  1. E. A. Ivleva
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  2. E. V. Simatova
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Correspondence to E. A. Ivleva.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 3, pp. 366–375 https://doi.org/10.31857/S0514749223030084.

Dedicated to Full Member of the Russian Academy of Sciences I.P. Beletskaya on her jubilee.

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Ivleva, E.A., Simatova, E.V., Zaborskaya, M.S. et al. Transformations of 3-(Bromomethyl)-5,7-dimethyl-2-oxaadamantan-1-ol in Sulfuric Acid. Russ J Org Chem 59, 409–416 (2023). https://doi.org/10.1134/S1070428023030089

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