Synthesis and Thermal Behavior of a Fused, Tricyclic 1,2,3,4-Tetrazine Ring System

This study presents the synthesis and characterization of a fused, tricyclic 1,2,3,4‐tetrazine ring system. The molecule is synthesized in a three‐step process from 5,5′‐dinitro‐bis,1,2,4‐triazole via a di‐N‐amino compound. Oxidation to form the azo‐coupled fused tricyclic 1,2,3,4‐tetrazine is achieved using tert‐butyl hypochlorite as the oxidant. The di‐N‐amino compound and the desired fused tricyclic 1,2,3,4‐triazine display interesting thermal behavior and are predicted to be high‐performance energetic materials. Ring of fire: Double N‐amination of the bis(tetraethylammonium) salt of 3,3′‐dinitro‐5,5′‐bi‐1,2,4‐triazole results in a thermally stable di‐N‐aminated energetic material that is insensitive to impact, spark, and friction. Subsequent oxidation leads to a fused, tricyclic 1,2,3,4‐tetrazine ring system (see figure) with excellent density and explosive performance properties.