Abstract
Previously undescribed sym-tetrazine monoazides were synthesized in order to study azidotetrazole tautomerism. It is shown that polar solvents shift the equilibrium to favor the formation of the tetrazole form. The effect of annelation on the electronic structure of the sym-tetrazine ring was examined using the Hückel MO method. The results of the calculation of the comparative stabilities in the order pyridine < pyridazine < 1,2,4-triazine < sym-tetrazine explain the peculiarities of the azide ⇋ tetrazole tautomeric equilibrium in the sym-tetrazine series.
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See [1] for communication III.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 711–715, May, 1971.
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Ershov, V.A., Postovskii, I.Y. Chemistry of sym-tetrazine. Chem Heterocycl Compd 7, 668–671 (1971). https://doi.org/10.1007/BF00945522
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DOI: https://doi.org/10.1007/BF00945522