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Synthesis of 3,5-Bis(hydroxymethyl)adamantan-1-ols and 3,5-Bis(nitrooxymethyl)adamantan-1-yl Nitrates

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Abstract

A convenient method has been developed for the synthesis of 3,5-bis(hydroxymethyl)adamantan-1-ols via successive nitroxylation of 1,3-bis(acetoxymethyl)adamantanes with fuming nitric acid, alkaline hydrolysis of intermediate 3,5-bis(acetoxymethyl)adamantane-1-yl nitrates, and reaction of the resulting 3,5-bis(hydroxymethyl)adamantan-1-yl nitrates with hydrazine hydrate. 3,5-Bis(hydroxymethyl)adamantan-1-ols have been converted to the corresponding trinitrates by treatment with fuming nitric acids in acetic anhydride.

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ACKNOWLEDGMENTS

This study was performed using scientific equipment of the “Physicochemical Properties of Substances and Materials” joint center at the Samara State Technical University.

Funding

This study was performed under financial support by the Russian Foundation for Basic Research (project no. 19-03-00973). Structural studies were carried out under financial support by the Ministry of Science and Higher Education of the Russian Federation in the framework of the project part of state assignment no. 0778-2020-0005.

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

    E. A. Ivleva, A. I. Kazakova & Yu. N. Klimochkin

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  1. E. A. Ivleva
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Correspondence to E. A. Ivleva.

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Ivleva, E.A., Kazakova, A.I. & Klimochkin, Y.N. Synthesis of 3,5-Bis(hydroxymethyl)adamantan-1-ols and 3,5-Bis(nitrooxymethyl)adamantan-1-yl Nitrates. Russ J Org Chem 56, 1562–1569 (2020). https://doi.org/10.1134/S1070428020090109

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