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3-(1-Adamantyl)Furazans

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Chemistry of Heterocyclic Compounds Aims and scope

The reactivity of 3-(1-adamantyl)-4-aminofurazan was studied. Upon treatment with oxidizing reagents the amino group is oxidized to azo, azoxy, and nitro groups. The nitration of 3-(1-adamantyl)-4-aminofurazan with nitric acid provided the corresponding nitroamine. The reaction of 3-(1-adamantyl)-4-nitrofurazan with nitrating and bromination agents takes place at the bridgehead position of the adamantane fragment and gives the corresponding nitroxyl and bromo derivatives. An X-ray structural analysis of 4,4′-di(1-adamantyl)azofurazan was undertaken.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    A. B. Sheremetev, A. M. Kozeev, N. S. Aleksandrova & M. I. Struchkova

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow, 119991, Russia

    K. Yu. Suponitsky

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  1. A. B. Sheremetev
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  2. A. M. Kozeev
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  3. N. S. Aleksandrova
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  4. M. I. Struchkova
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Correspondence to A. B. Sheremetev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1457-1468, September, 2013.

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Sheremetev, A.B., Kozeev, A.M., Aleksandrova, N.S. et al. 3-(1-Adamantyl)Furazans. Chem Heterocycl Comp 49, 1358–1369 (2013). https://doi.org/10.1007/s10593-013-1385-z

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