Dinitromethyl‐3(5)‐1,2,4‐oxadiazole Derivatives from Controllable Cyclization Strategies
Abstract
N‐Cyanoimidate (1) with hydroxylamine hydrochloride in the presence of triethylamine gives different products (2 a or 2 b) as a function of the sequence of reactant addition. Further oxidation/nitration/decarboxylation/acidification reactions of 2 a/2 b generate dinitromethyl‐3(5)‐1,2,4‐oxadiazole derivatives, including a surprising energetic compound with high oxygen balance, 3‐(dinitromethyl)‐1,2,4‐oxadiazol‐5‐one (5) as well as 5,5′‐dinitromethyl‐3,3′‐azo‐1,2,4‐oxadiazole (9). Some salts of 5 and 9 as precursors were also prepared. All were fully characterized using multinuclear NMR and IR spectroscopy, and elemental analyses as well as low‐temperature single‐crystal X‐ray diffraction for 4, 5, 7 and 8. In addition, their properties (thermal stability, detonation performance and sensitivity to impact and friction) were investigated. Among them, 5 and 8 show promising detonation performance as energetic materials.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Oct 25, 2017
- Source ID
- 10.1002/chem.201704446
Entities
People
- Chunlin He
- Damon A. Parrish
- Gregory H Imler
- Jean'ne Shreeve
- Yongxing Tang
Organizations
- Defense Threat Reduction Agency
- M J Murdock Charitable Trust
- Office of Naval Research
- United States Naval Research Laboratory
- University of Idaho