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Synthesis and Chemical Transformations of 1-Aryladamantanes

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Abstract

1-Aryladamantanes were synthesized, and their transformations in fuming nitric acid were studied. The nitroxylation of the saturated framework are accompanied by the nitration of the aromatic moiety and form 3-(dinitroaryl)adamantan-1-yl nitrates. A number of new polyfunctional compounds were synthesized by the reactions of substituted 3-(dinitroaryl)adamantan-1-yl nitrates with nucleophiles in concentrated sulfuric acid. Due to their polyfunctionality, the compounds obtained can be used as starting substrates in the synthesis of substances with a wide range of biological activity and materials with a complex of valuable properties.

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ACKNOWLEDGMENTS

The work was carried out using the scientific equipment of the “Study of the Physical and Chemical Properties of Substances and Materials” Center for Collective Use, Samara State Technical University.

Funding

The research was financially supported by the Russian Science Foundation (project no. 21-73-20103) (the 13C NMR spectra were recorded using the equipment of the “New Materials and Resource-Saving Technologies” Center for Collective Use, Lobachevskii Nizhny Novgorod State University). The other spectral data were obtained with the support of the Ministry of Science and Higher Education of the Russian Federation (subject no. FSSE-2023-0003) in the framework of the state assignment for the Samara State Technical University.

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

    E. A. Ivleva, N. S. Orlinskii, M. S. Zaborskaya & Yu. N. Klimochkin

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  1. E. A. Ivleva
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  2. N. S. Orlinskii
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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 11, pp. 1465–1481 https://doi.org/10.31857/S0514749223110083.

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Ivleva, E.A., Orlinskii, N.S., Zaborskaya, M.S. et al. Synthesis and Chemical Transformations of 1-Aryladamantanes. Russ J Org Chem 59, 1901–1915 (2023). https://doi.org/10.1134/S1070428023110088

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