Boosting energetic performance by trimerizing furoxan

The introduction of N-oxides is a useful approach in improving oxygen balance, density and detonation properties of energetic compounds. Here we present the design and syntheses of a new series of trifuroxan compounds 4-6. The structures of 4 and 5 were determined by single crystal X-ray diffraction. Compound 5 is the first representative of furoxan fused 1,2-diazocine. The zero oxygen balance along with moderate sensitivities (IS = 19 J, FS = 80 N) and detonation properties (D = 9417 m s^-1, P = 39.2 GPa) of compound 5 makes it a promising replacement for RDX and HMX. The high density, positive oxygen balance and detonation properties of compound 6 which approach those of CL-20 may help it to find potential application as a high energy density oxidizer.