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Selective Nitroxylation of Adamantane Derivatives in the System Nitric Acid–Acetic Anhydride

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Abstract

A number of new nitroxyadamantanes have been synthesized by nitroxylation of the corresponding substrates with nitric acid in acetic anhydride. High electrophilicity and reduced acidity of the system HNO3–Ac2O increases the stability of nitrates and significantly decreases the probability of formation of alcohols. In some cases, nitrolysis and oxidation of functional groups in the substrate are observed.

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ACKNOWLEDGMENTS

This study was performed using the facilities of the “Physicochemical Properties of Substances and Materials” joint center of the Sanara State Technical University.

Funding

This study was performed under financial support by the Ministry of Science and Higher Education of the Russian Federation (project part of state assignment no. 0778-2020-0005). The study of nitroxylation of haloadamantane derivatives was financially supported by the Russian Foundation for Basic Research (project no. 20-03-00869).

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

    Yu. N. Klimochkin, E. A. Ivleva & I. K. Moiseev

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  1. Yu. N. Klimochkin
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  2. E. A. Ivleva
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  3. I. K. Moiseev
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Correspondence to E. A. Ivleva.

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Klimochkin, Y.N., Ivleva, E.A. & Moiseev, I.K. Selective Nitroxylation of Adamantane Derivatives in the System Nitric Acid–Acetic Anhydride. Russ J Org Chem 56, 1532–1539 (2020). https://doi.org/10.1134/S1070428020090055

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