This work reportst he first compound containing both at etrazole and an azasydnone ring, au nique energetic material. Severale nergetic salts of the tetrazole azasydnone were synthesized and characterized,l eadingt o the creation of new secondary and primary explosives. Molecular structures are confirmed by 1 Ha nd 13 CNMR, IR spectroscopy,a nd X-ray crystallographic analysis. The high heats of formation, fast detonation velocities, and straightforward synthesis of energetic azasydnones should capture the attention of future energetics research.

The first compound containing both a tetrazole and an azasydnone ring, a unique energetic material, is reported. Several energetic salts of the tetrazole azasydnone were synthesized and characterized, leading to the creation of new secondary and primary explosives. Molecular structures are confirmed by 1H and 13C NMR, IR spectroscopy, and X‐ray crystallographic analysis. The high heats of formation, fast detonation velocities, and straightforward synthesis of energetic azasydnones should capture the attention of future energetics research. More information can be found in the Communication by D. G. Piercey et al. on page 14530.

In this report, we describe the application of an electrocyclization toward the synthesis of a high-nitrogen heterocycle. It entails the synthesis of a novel, high-nitrogen, 2-3-disubstituted tetrazolium salt via the tetraaza-Nazarov cyclization (4π electrocyclization) of 3-bromo-1,5-bis(3-nitro-1,2,4-triazole-1H-5-yl)-formazan (BDNF). The cyclization takes place under mild conditions using the oxidant phenyliodine(III) diacetate (PIDA). The proposed electrocyclic mechanism is supported by density functional theory (DFT) calculations and data from previous studies of formazan cyclizations. This is noteworthy because while 4π electrocyclizations with one or two nitrogen atoms have been documented previously, this case represents the first example of generation and cyclization of a conjugated intermediate with four nitrogen atoms. The experimental behavior of electrocyclization is consistent with the predictions of DFT.