Assembling high nitrogen isomeric energetic molecules via a lithium-mediated concerted [2+3] reaction of two diazo compounds

The search for high nitrogen isomeric energetic molecules and comparison of their structure-property relationship are always attractive in the field of energetic materials. In this paper, a novel lithium-mediated concerted [2 + 3] reaction with two diazo compounds has been accomplished which leads to the simultaneous formation of two isomeric cyanotetrazoles (2a and 2b). The cyano group in cyanotetrazoles was further converted to tetrazole or tetrazole N-oxide to form tricyclic heterocyclic products (3a, 3b, 7a, and 7b). The energetic properties of the compounds were studied. A representative compound 3a (T-d = 220 degrees C, D = 9052 m s(-1), IS = 13 J, FS = 200 N) has better detonation performances, higher thermal stability and lower mechanical sensitivities than RDX, which is expected to serve as a potential energetic material.

Automated summary

In this study, two isomeric compounds were synthesized using a new method, and their energetic properties were examined. The results showed that one of the compounds exhibited better detonation performance, higher thermal stability, and lower mechanical sensitivities, suggesting its potential as an energetic material.