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Adamantylazoles: XI. Reaction of 1-phenyltetrazole-5-thione with adamantan-1-ol in strong acids

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Abstract

The reaction of 1-phenyltetrazole-5-thione with adamantan-1-ol in sulfuric acid gave 3-(1-adamantyl)-1-phenyltetrazole-5-thione having a mesoionic structure, 5-(1-adamantylsulfanyl)-1-phenyltetrazole, and 3-(1-adamantyl)-5-(1-adamantylsulfanyl)-1-phenyltetrazolium hydrogen sulfate. Hydrolysis of 5-(1-adamantylsulfanyl)-1-phenyltetrazole led to the formation of 1-phenyltetrazol-5-one. The adamantylation process is reversible.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology (Technical University), Moskovskii pr. 26, St. Petersburg, 190013, Russia

    A. V. Logvinov, V. V. Saraev & E. L. Golod

  2. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, Russia

    I. N. Polyakova

  3. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia

    Yu. A. Strelenko

Authors
  1. A. V. Logvinov
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  2. V. V. Saraev
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  3. I. N. Polyakova
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  4. Yu. A. Strelenko
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  5. E. L. Golod
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Correspondence to A. V. Logvinov.

Additional information

Original Russian Text © A.V. Logvinov, V.V. Saraev, I.N. Polyakova, Yu.A. Strelenko, E.L. Golod, 2007, published in Zhurnal Obshchei Khimii, 2007, Vol. 77, No. 12, pp. 2041–2046.

For communication X, see [1].

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Logvinov, A.V., Saraev, V.V., Polyakova, I.N. et al. Adamantylazoles: XI. Reaction of 1-phenyltetrazole-5-thione with adamantan-1-ol in strong acids. Russ J Gen Chem 77, 2186–2191 (2007). https://doi.org/10.1134/S1070363207120171

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  • DOI: https://doi.org/10.1134/S1070363207120171

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