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nitrimino tetrazoles

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"Energetic Mono-, Di-, and Trisubstituted Nitroiminotetrazoles", Young-Hyuk Joo,  Jean'ne M. Shreeve M. Shreeve.                                                                                             Angewandte Chemie. Volume 48, Issue 3, pages 564–567, January 5, 2009
  
reaction of 4-amino,5-nitrotriazole with and NaN3, bromocyanide, then a nitration, may give the above compound,

which should be both somewhat more  resistant to impact and more powerful than HMX. The nitrimino group should be stabilized by electron donation from the NH group in the ring, analogous to the stability of nitroguanidine.

Explaining why there are no --NHNO2 groups,  the segment R--NH--C(R)=N--NO2 has a resonance of                                                                    R--NH(+)=C(R)--N=N(+)[ --O(-) ]2 , which is more stable than the primary nitramine structure.

 

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