Transamination Reactions of 1,1-Diamino-2,2-Dinitroethene (FOX-7)

Abstract

Treatment of 1,1-diamino-2,2-dinitroethene (FOX-7) with a variety of amines and hydrazine, results in at least one, and in some cases both, of the amino groups being replaced to give N-substituted and N,N'-disubstituted 1,1-diamino-2,2-dinitroethenes.

1,1-Diamino-2,2-dinitroethene (DADNE, FOX-7) – Properties and Formulations (a Review)

“…The unique characteristics of FOX-7 result from its molecular structure [7], which is beneficial for the creation of strong inter-and intra-molecular hydrogen bonds for stabilizing the molecule. Since 1998, when FOX-7 was first synthesized by Latypov et al [8], it has been the subject of many experimental investigations [9][10][11][12][13][14][15][16][17][18][19][20][21][22]. FOX-7 has a favorable oxygen balance and the decomposition of the molecule can produce entirely gaseous products (CO, H 2 O, N 2 ).…”

Thermal Behavior of 2‐(Dinitromethylene)‐1,3‐diazacyclopentane

“…[14][15][16] We prepared a new derivative of FOX-7-2-(dinitromethylene)-1,3-diazacyclopentane (DNDZ), 14 and found it had the same structure features as FOX-7 and existed in many manifold tautomers and resonances (Scheme 1). It also could react with strong alkali (KOH), and we have used it to prepare a new high-energy organic potassium salt, which will be used as flame suppressor in propellant to substitute inorganic potassium salt (KCl, K 2 SO 4 , KNO 3 and K 3 AlF 6 ) to generate much more energy and clean gas.…”

“…So, FOX-7 exists in manifold tautomers and resonances and can react with some nucleophiles to synthesize new high energy derivatives. [3][4][5] Our interest mainly consisted in modifying molecular structure of FOX-7 in order to obtain some new high energetic compounds and researching their relationship of structure-property. [14][15][16] We prepared a new derivative of FOX-7-2-(dinitromethylene)-1,3-diazacyclopentane (DNDZ), 14 and found it had the same structure features as FOX-7 and existed in many manifold tautomers and resonances (Scheme 1).…”

“…Many researches have been carried out on the synthesis, mechanism, molecule structure, thermal behavior, explosive performance and application of FOX-7. [2][3][4][5][6][7][8][9][10][11][12] According to the molecular structure features, FOX-7 is a special "push-pull" nitro-enamine 13 and possesses a highly polarized carbon-carbon double bond with positive and negative charges being stabilized by the two amino groups and two nitro groups, respectively. So, FOX-7 exists in manifold tautomers and resonances and can react with some nucleophiles to synthesize new high energy derivatives.…”

Thermal Behaviors of 2‐(Dinitromethylene)‐1,3‐diazacycloheptane (DNDH)

“…FOX-7 is a special "push-pull" nitro-enamine 26 and can react with nucleophiles to synthesize some new high energy derivatives. 5,13,16 Our interest mainly consisted in modifying molecular structure of FOX-7 in order to obtain some new high energetic compounds and researching their relationship of structure-property. [27][28][29][30][31][32][33][34][35] We have prepared a new derivative of FOX-7, 2-(dinitromethylene)-1,3-diazacycloheptane (DNDH).…”