Enhanced Energetic Performance via the Combination of Furoxan and Oxa-[5,5]bicyclic Structures

Abstract

Three new compounds based on the combination of furoxan (1,2,5-oxadiazole N-oxide) and oxa-[5,5]bicyclic ring were synthesized. Among them, the nitro compound showed satisfactory detonation properties (Dv, 8565 m s−1; P, 31.9 GPa), which is comparable to the performance of RDX (a classic high-energy secondary explosive). Additionally, the introduction of the N-oxide moiety and oxidation of the amino group more effectively improved the oxygen balance and density (d, 1.81 g cm−3; OB%, +2.8%) of the compounds compared to furazan analogues. Combined with good density and oxygen balance as well as moderate sensitivity, this type of furoxan and oxa-[5,5]bicyclic structure will open up a platform for the synthesis and design of new high-energy materials.

Convenient Preparation, Thermal Properties and X-ray Structure Determination of 2,3-Dihydro-5,6,7,8-tetranitro-1,4-benzodioxine (TNBD): A Promising High-Energy-Density Material

“…Although mixed O,N-heterocycles, such as 1,2,5-, 1,2,4-and 1,3,4-oxadiazoles [16][17][18][19][20], as well as oxadiazole N-oxides (furoxans) [21][22][23][24][25][26], are now amongst the most popular newly designed energetic compounds [27], derivatives of "pure" O-heterocycles as energetic materials have hardly been mentioned in the scientific literature (except for unstable cyclic peroxides) [28]. 1,4-Benzodioxane (also known as 1,2-ethylenedioxybenzene, benzo-1,4dioxane (old chemical names) or 2,3-dihydro-1,4-benzodioxin (new systematic name)) is one of many benzene-annulated oxygen O-heterocycles [29].…”

Convenient Preparation, Thermal Properties and X-Ray Structure Determination of 2,3-Dihydro-5,6,7,8-tetranitro-1,4-benzodioxine (TNBD): a Promising High Energy Density Material (HEDM)

“…Althought mixed O,N-heterocycles, such as 1,2,5-, 1,2,4-and 1,3,4-oxadiazoles [16][17][18][19][20], as well as oxadiazole N-oxides (furoxans) [21][22][23][24][25][26] , are now amongst the most popular newly designed energetic compounds [27], derivatives of "pure" O-heterocycles as energetic materials have hardly been mentioned in scientific literature (except for unstable cyclic peroxides) [28]. 1,4-Benzodioxane (also known as 1,2-ethylenedioxybenzene, benzo-1,4-dioxane (old chemical names) or 2,3-dihydro-1,4-benzodioxin (new systematic name)) is one of many benzene annulated oxygen O-heterocycles [29].…”