Abstract
Scholars from around the world have been attempting to simplify and cheapen the synthetic method for the promising high-energy compound CL-20 for decades. The lack of understanding of the formation mechanisms of hexaazaisowurtzitane derivatives―CL-20 precursors―is a barrier to solving the said problems. Here, we report the results from an in-depth study into the acid-catalyzed condensation between benzamide and glyoxal in a molar ratio of 2:1 in polar protic and aprotic solvents. Sixteen compounds were isolated and identified, of which eight were synthesized for the first time. A geminal diol, N,N’-(2,2-dihydroxyethane-1,1-diyl)dibenzamide, was synthesized. Two isomers of 1,2-bis(benzoylamino)-1,2-ethanediol were isolated and identified. N,N’-(1-oxoethane-1,2-diyl)dibenzamide and 2-oxo-2-[(phenylcarbonyl)amino]ethyl benzoate were produced that were likely formed due to the 1,2-hydride shift. N-polysubstituted 1,4-dioxane-2,3,5,6-tetramine was synthesized for the first time, whose structure may be of interest as a scaffold for new explosives. DMSO, THF and HCOOH were found to be able to engage in a reaction with benzamide, or condensation products thereof, and glyoxal under acid-catalyzed conditions.
Highlights
Academic Editor: Weihua ZhuThe evolution of defense technology has a direct association with developing new highenergy materials that are superior in their energy-mass and performance characteristics to the existing ones.Polyheterocyclic caged nitramines are viewed as the most promising among the highenergy density compounds
The predictions demonstrate that caged nitramines are much more attractive in seeking high-energy materials because they feature enhanced energetic characteristics and reduced sensitivity [1,2,3,4,5,6,7,8,9,10]
Study into Condensation of Benzamide withaGlyoxal tivesWe were obtained, some polyheterocyclic caged systems weresubstituted discovered sulfonamides and new conhave previously explored the condensation between densation regularities were established
Summary
The evolution of defense technology has a direct association with developing new highenergy materials that are superior in their energy-mass and performance characteristics to the existing ones. Polyheterocyclic caged nitramines are viewed as the most promising among the highenergy density compounds. These compounds structurally contain strained moieties and have compact rigid molecules, which enhances their energy-mass characteristics. The predictions demonstrate that caged nitramines are much more attractive in seeking high-energy materials because they feature enhanced energetic characteristics and reduced sensitivity [1,2,3,4,5,6,7,8,9,10]. CL-20 excels compared to the other high-energy explosive materials such as HMX, RDX, PETN, etc. Despite the merits of CL-20, its wide application is hindered by its high manufacturing cost
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