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Mass spectral fragmentation of 1,5-disubstituted tetrazoles and rearrangement of the resulting nitrenes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

In agreement with the thermolysis characteristics of 1,5-disubstituted tetrazoles, the fragmentation pattern of 1-(o-, m-, and p-tolyl)-5-phenyltetrazoles has been shown to consist of a sequence of reactions, namely, initial tautomeric conversion to an azide structure, followed by elimination of a molecule of nitrogen, and rearrangement of the resulting nitrene intermediate to a cation-radical derivative of a methyl-substituted 2-phenylbenzimidazole compound. In the case of 1-(o-tolyl)-5-phenyltetrazole an alternative pathway is observed, involving cyclization of the nitrene intermediate at the methyl group (an insertion reaction into a C-H bond) to form dihydroquinazoline derivatives. An analogous cyclization process has been noted for the thermolysis process as well.

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Authors and Affiliations

  1. K. A. Timiryazev Moscow Academy of Agriculture, Moscow

    Yu. V. Shurukhin, A. V. Dovgilevich, I. I. Grandberg & B. P. Baskunov

Authors
  1. Yu. V. Shurukhin
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  2. A. V. Dovgilevich
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  3. I. I. Grandberg
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  4. B. P. Baskunov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 925–930, July, 1988.

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Shurukhin, Y.V., Dovgilevich, A.V., Grandberg, I.I. et al. Mass spectral fragmentation of 1,5-disubstituted tetrazoles and rearrangement of the resulting nitrenes. Chem Heterocycl Compd 24, 760–764 (1988). https://doi.org/10.1007/BF00633171

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  • DOI: https://doi.org/10.1007/BF00633171

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