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Reaction of 5-Substituted tetrazoles with trifluoroacetic anhydride

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Abstract

5-Substituted tetrazoles readily react with trifluoroacetic anhydride at 20–25°C to give the corresponding 2-substituted 5-trifluoromethyl-1,3,4-oxadiazoles, in contrast to published data according to which the title compounds are converted into 1,3,4-oxadiazole derivatives on heating with carboxylic acid anhydrides or chlorides at 100–120°C. The reaction is governed not only by the rate of acylation of the tetrazole ring and temperature conditions but also by the stability of intermediate N-acyltetrazoles.

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Authors and Affiliations

  1. Institute of Petroleum and Coal-Chemical Synthesis, Irkutsk State University, ul. K. Marksa 1, Irkutsk, 664003, Russia

    L. I. Vereshchagin, O. N. Verkhozina, F. A. Pokatilov, S. K. Strunevich, A. G. Proidakov & V. N. Kizhnyaev

Authors
  1. L. I. Vereshchagin
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  2. O. N. Verkhozina
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  3. F. A. Pokatilov
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  4. S. K. Strunevich
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  5. A. G. Proidakov
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  6. V. N. Kizhnyaev
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Corresponding author

Correspondence to V. N. Kizhnyaev.

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Original Russian Text © L.I. Vereshchagin, O.N. Verkhozina, F.A. Pokatilov, S.K. Strunevich, A.G. Proidakov, V.N. Kizhnyaev, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 11, pp. 1709–1713.

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Vereshchagin, L.I., Verkhozina, O.N., Pokatilov, F.A. et al. Reaction of 5-Substituted tetrazoles with trifluoroacetic anhydride. Russ J Org Chem 43, 1710–1714 (2007). https://doi.org/10.1134/S1070428007110218

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  • DOI: https://doi.org/10.1134/S1070428007110218

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