Improved Preparation of 3-Oximinooxetane - An Important Precursor to Energetic Oxetanes

Born, Max; Karaghiosoff, Konstantin and Klapötke, Thomas M. (2022): Improved Preparation of 3-Oximinooxetane - An Important Precursor to Energetic Oxetanes. In: Propellants Explosives Pyrotechnics, Vol. 47, No. 3

Abstract

Oximes represent an extremely versatile building block in energetic materials chemistry. While oxidation with peroxy acids affords the corresponding mononitro compounds, tandem oxidation-nitration reactions such as the Scholl reaction lead to geminal dinitro compounds. Furthermore, the corresponding amines can be obtained by reduction of the oxime group. Accordingly, 3-oximinooxetane represents a suitable precursor for 3-nitro- and 3,3-dinitrooxetane as well as 3-aminooxetane. 3-Oximinooxetane, which is poorly described in the literature, has now been extensively characterized by vibrational-, mass- and NMR spectroscopy, as well as elemental and thermal analysis. In addition, its synthesis has been significantly improved compared to literature. The molecular structure was elucidated by single-crystal X-ray diffraction. Since 3-oximinooxetane is energetic by itself, its performance was calculated using the EXPLO5 V6.04 thermochemical code, and its sensitivity towards external stimuli such as impact, friction, and electrostatic discharge was determined by BAM standard procedures.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0721-3115
• Language: English
• DFG: Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 491502892