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2-Nitroguanidine Derivatives: VI. Synthesis and Chemical Properties of Hydrazo- and Azobis(nitroformamidine)

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Abstract

New methods have been proposed for the synthesis of hydrazobis(nitroformamidine), and its reactions with electrophilic reagents, formaldehyde and glyoxal, have been studied. Oxidation of hydrazobis-(nitroformamidine) with atmospheric oxygen in glacial acetic acid in the presence of a catalytic amount of N2O4 gives crystalline azobis(nitroformamidine). Ionization constants of the oxidation product, determined by potentiometric titration (pKa 1 = 3.50, pKa 2 = 7.93), indicate considerable increase in the NH acidity as compared to 2-nitroguanidine. Reactions of azobis(nitroformamidine) with β-dicarbonyl compounds lead to formation of 1-diacylmethyl-N' 1,N' 2-dinitrohydrazine-1,2-dicarboximidamides.

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Authors
  1. E. L. Metelkina
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Metelkina, E.L. 2-Nitroguanidine Derivatives: VI. Synthesis and Chemical Properties of Hydrazo- and Azobis(nitroformamidine). Russian Journal of Organic Chemistry 40, 928–935 (2004). https://doi.org/10.1023/B:RUJO.0000045193.49958.c4

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  • DOI: https://doi.org/10.1023/B:RUJO.0000045193.49958.c4

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