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Adamantylazoles: XII. Alkylation of 1-R-tetrazole-5-thiones and 1-R-tetrazol-5-ones with tertiary alcohols in sulfuric acid

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Abstract

1-R-Substituted tetrazole-5-thiones reacted with adamantan-1-ol in sulfuric acid to give mesoionic 1-R-3-(1-adamantyl)tetrazolium-5-thiolates, isomeric 1-R-5-(1-adamantylsulfanyl)tetrazoles, 1-R-4-(1-adamantyl) tetrazole-5-thiones, and 1-R-3-(1-adamantyl)-5-(1-adamantylsulfanyl)tetrazolium salts. Adamantylation of 1-R-tetrazol-5-ones under analogous conditions afforded only the corresponding mesoionic 1-R-3-(1-adamantyl)tetrazolium-5-olates. Mesoionic 1-R-3-tert-butyltetrazolium-5-thiolates and 1-R-3-tert-butyltetrazolium-5-olates were obtained by alkylation of the same substrates with tert-butyl alcohol in sulfuric acid.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 190013, Russia

    A. V. Logvinov & E. L. Golod

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

    I. N. Polyakova

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  1. A. V. Logvinov
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  2. I. N. Polyakova
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  3. E. L. Golod
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Correspondence to E. L. Golod.

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Original Russian Text © A.V. Logvinov, I.N. Polyakova, E.L. Golod, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 10, pp. 1726–1734.

For communication XI, see [1].

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Logvinov, A.V., Polyakova, I.N. & Golod, E.L. Adamantylazoles: XII. Alkylation of 1-R-tetrazole-5-thiones and 1-R-tetrazol-5-ones with tertiary alcohols in sulfuric acid. Russ J Gen Chem 79, 2220–2229 (2009). https://doi.org/10.1134/S1070363209100235

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