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

Fessard, Thomas C.; Gospodinov, Ivan; Klapötke, Thomas M.; Stierstorfer, Jörg und Voggenreiter, Michael (2022): Energetic but insensitive spiro-tetrahydrotetrazines based on oxetane-3-one. In: Journal of Heterocyclic Chemistry, Bd. 59, Nr. 10: S. 1781-1789

Abstract

Energetic 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 (H-1 and C-13). 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.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 0022-152X
• Sprache: Englisch
• DFG: Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 491502892