Energetic but insensitive spiro‐tetrahydrotetrazines based on oxetane‐3‐one

Abstract

AbstractEnergetic oxetanes were first described in the 1970s, such as 3,3‐bis(azidomethyl)oxetanes (BAMO) and 3‐(nitratomethyl)‐3‐(methyl)oxetanes (NIMMO). Over the past few years, oxetanes were hardly available only as special‐purpose chemicals for the pharmaceutical industry. Oxetan‐3‐one is condensed with energetic compounds with a hydrazino function such as amino‐nitroguanidine and picryl hydrazine to form energetic Schiff bases. Hydrazinolysis of the guanidine derivatives lead to energetic spiro‐tetrahydrotetrazines which are quite rare in literature. All products were characterized by their crystal structure using single‐crystal X‐ray diffraction. Furthermore, the new compounds were analyzed using IR, EA, DTA, and multinuclear NMR spectroscopy (1H and 13C). The sensitivities towards external stimuli such as friction and impact were determined according to BAM standards and the energetic performances were calculated using the EXPLO5 code.