Energetic Azoxy‐Coupled Tetrazoles

ABSTRACT Azoxy coupling of 5‐amino‐1‐methyl‐tetrazole, 5‐amino‐2‐methyl‐tetrazole, and 5‐amino‐1‐methoxy‐tetrazole was performed by reacting each with various oxidants. These reactions revealed aqueous Oxone to be the most facile system for yielding the azoxy couple for the previously mentioned tetr...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2024-11, Vol.61 (11), p.1704-1709
Main Authors: Scherschel, Nicholas F., Zeller, Matthias, Piercey, Davin G.
Format: Article
Language:English
Subjects:
azoxy‐couple
Chemical reactions
energetic materials
Impact analysis
NMR
Nuclear magnetic resonance
Oxidizing agents
Sensitivity analysis
Single crystals
Structural analysis
Tetrazoles
X-ray diffraction
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Summary:ABSTRACT Azoxy coupling of 5‐amino‐1‐methyl‐tetrazole, 5‐amino‐2‐methyl‐tetrazole, and 5‐amino‐1‐methoxy‐tetrazole was performed by reacting each with various oxidants. These reactions revealed aqueous Oxone to be the most facile system for yielding the azoxy couple for the previously mentioned tetrazoles. Chemical and structural characterization of each novel azoxy‐coupled tetrazole was conducted with 1H NMR, 13C NMR, HRMS, and single‐crystal x‐ray diffraction. Energetic characterization was evaluated by analysis of each compounds' single crystal x‐ray diffraction density, impact sensitivity, friction sensitivity, and decomposition temperature. All compounds were found to be very sensitive to impact and friction stimuli. 5‐Amino‐2‐methyl‐tetrazole, above, left, when reacted with Oxone affords a transiently stable nitroso intermediate (blue solution). When the nitroso is reacted to completion, 5,5′‐azoxy‐bis‐2,2′‐methyl‐tetrazole is yielded as yellow rods. For scale reference, the microscope slide the crystals rest on is 22 mm × 22 mm.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4881