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Reaction of N-alkyl-N′-(trimethylsilyl)carbodiimides with nitrating agents. The synthesis of N-(tert-butyl)-N′-nitrocarbodiimide

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Abstract

Reaction of N-Alk-N′-(trimethylsilyl)carbodiimides (Alk = Me, But) with nitrating agents (N2O5, (NO2)2SiF6) affords alkyl(nitro)cyanamides and N-alkyl-N′-nitrocarbodiimides. The product ratio depends on the reaction conditions. N-(tert-butyl)-N′-nitrocarbodiimide can be obtained in almost pure form. This compound is stable at temperatures below 10 °C. Its structure was confirmed by 1Н, 13C, and 14N NMR. The reaction of N-(tert-butyl)-N′-nitrocarbodiimide with amines provides a new route to N-alkyl(aryl)-substituted N′-(tert-butyl)-N″-nitroguanidines.

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Authors and Affiliations

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

    A. M. Churakov, S. L. Ioffe, A. A. Voronin & V. A. Tartakovsky

Authors
  1. A. M. Churakov
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  2. S. L. Ioffe
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  3. A. A. Voronin
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  4. V. A. Tartakovsky
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Corresponding author

Correspondence to A. M. Churakov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0056—0060, January, 2018.

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Churakov, A.M., Ioffe, S.L., Voronin, A.A. et al. Reaction of N-alkyl-N′-(trimethylsilyl)carbodiimides with nitrating agents. The synthesis of N-(tert-butyl)-N′-nitrocarbodiimide. Russ Chem Bull 67, 56–60 (2018). https://doi.org/10.1007/s11172-018-2037-3

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  • DOI: https://doi.org/10.1007/s11172-018-2037-3

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