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Nitration and bromination of benzo-1,2,3,4-tetrazine 1,3-dioxides

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Abstract

Benzo-1,2,3,4-tetrazine 1,3-dioxide (BTDO) and its derivatives were nitrated with HNO3/H2SO4 or HNO3/oleum and brominated with dibromoisocyanuric acid in CF3CO2H/H2SO4 (5 : 1) or H2SO4. The reactivity of positions in the benzene ring of this heterocyclic system as regards electrophilic substitution was found to change in the following order: 5 ≈ 7 > 8 > 6. Mono- and dinitro-BTDOs and mono- and polybromo-BTDOs were synthesized. Their structures were confirmed by 1H, 13C, and 14N NMR spectra.

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Authors and Affiliations

  1. Russian Academy of Sciences, N. D. Zelinsky Institute of Organic Chemistry, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    O. Yu. Smirnov, A. M. Churakov, Yu. A. Strelenko, S. L. Ioffe & V. A. Tartakovsky

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  1. O. Yu. Smirnov
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  2. A. M. Churakov
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  3. Yu. A. Strelenko
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  4. S. L. Ioffe
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  5. V. A. Tartakovsky
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Smirnov, O.Y., Churakov, A.M., Strelenko, Y.A. et al. Nitration and bromination of benzo-1,2,3,4-tetrazine 1,3-dioxides. Russian Chemical Bulletin 51, 1841–1848 (2002). https://doi.org/10.1023/A:1021344300420

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  • DOI: https://doi.org/10.1023/A:1021344300420

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