Strategy for Extending the Nitrogen Chain: The Bis(1,2,3-triazole) Formation Reaction from Tosylhydrazones and -Amino Azole.

A facile and versatile synthesis strategy for the bis(1,2,3-triazole) formation reaction was developed from tosylhydrazones and -amino (-NH) azole instead of -amino amine derivatives. The novel energetic compounds containing the bicycle catenated six-nitrogen chain (N) and the first example of N neutral compounds were synthesized in a moderate or high yield. The possible mechanism of bis(1,2,3-triazole) formation reaction based on amino azole of -NH was verified by the X-ray crystal structure of key intermediates. In addition, four energetic compounds , and containing N and N structures possess acceptable decomposition temperatures (150.1-201.6 °C) and moderate calculated detonation performances (6850-7727 m/s). Among them, (N structure) and (N structure) could be used as the melt-cast explosive candidate and the gas generation agent candidate, respectively. This type of nitrogen-nitrogen bonding formation opens a new method for discovery of novel high-nitrogen energetic compounds containing catenated multiple nitrogen atoms especially odd number nitrogen compounds.