SUBSTITUTION REACTIONS OF 1,1 -DIAMINO-2.2-DINITROETHENE (FOX-7)

摘要

1,1-Diamino-2,2-dinitroethene (FOX-7) is a thermally stable, impact insensitive explosive with a calculated performance close to that of RDX. In order to explore the chemical stability of 1,1-diamino-2,2-dinitroethene, we have studied its reactivity towards nucleophilic species such as amines (predominantly primary amines), hydrazine and guanidine. At least one, and in some cases both, of the amino groups can be replaced by transamination, to give N-substituted and N,N'-disubstituted 1,1-diamino-2,2-dinitroethenes by reaction with amines, and 1-amino-1-hydrazino-2,2-dinitroethene by reaction with hydrazine. The latter forms a hydrazinium salt with excess hydrazine. With guanidine, deprotonation to form the guanidinium salt of the conjugate base of 1,1-diamino-2,2-dinitroethene occurs in preference to transamination. This work has generated several new energetic compounds and has given a better understanding of the chemical stability of 1,1-diamino-2,2-dinitroethene.