Nitrogen‐Rich Energetic 1,2,5‐Oxadiazole‐Tetrazole – Based Energetic Materials

Klapötke, Thomas M.; Witkowski, Tomasz

doi:10.1002/prep.201400294

Cited by 68 publications

(40 citation statements)

References 82 publications

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“…[104,105] They are commonly synthesized by the [3 + 2] cycloaddition of metal or organic azides to nitriles in organic solvents. [104,105] They are commonly synthesized by the [3 + 2] cycloaddition of metal or organic azides to nitriles in organic solvents.…”

Section: Il-mediated Preparation Of Other Energetic Compoundsmentioning

confidence: 99%

“…High-enthalpy polynitrogen heterocycles, tetrazoles, are applied in materials science and medicinalc hemistry as prospective explosives, components of information recording systems, and carboxylic acids urrogates. [104,105] They are commonly synthesized by the [3 + 2] cycloaddition of metal or organic azides to nitriles in organic solvents. These reactions that involve explosive and toxic azide substrates andi ntermediates require high temperatures (> 100 8C), which makes them dangerous.…”

Section: Il-mediated Preparation Of Other Energetic Compoundsmentioning

confidence: 99%

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Prospective Symbiosis of Green Chemistry and Energetic Materials

et al. 2017

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A global increase in environmental pollution demands the development of new "cleaner" chemical processes. Among urgent improvements, the replacement of traditional hydrocarbon-derived toxic organic solvents with neoteric solvents less harmful for the environment is one of the most vital issues. As a result of the favorable combination of their unique properties, ionic liquids (ILs), dense gases, and supercritical fluids (SCFs) have gained considerable attention as suitable green chemistry media for the preparation and modification of important chemical compounds and materials. In particular, they have a significant potential in a specific and very important area of research associated with the manufacture and processing of high-energy materials (HEMs). These large-scale manufacturing processes, in which hazardous chemicals and extreme conditions are used, produce a huge amount of hard-to-dispose-of waste. Furthermore, they are risky to staff, and any improvements that would reduce the fire and explosion risks of the corresponding processes are highly desirable. In this Review, useful applications of almost nonflammable ILs, dense gases, and SCFs (first of all, CO ) for nitration and other reactions used for manufacturing HEMs are considered. Recent advances in the field of energetic (oxygen-balanced and hypergolic) ILs are summarized. Significant attention is paid to the SCF-based micronization techniques, which improve the energetic performance of HEMs through an efficient control of the morphology and particle size distribution of the HEM fine particles, and to useful applications of SCFs in HEM processing that makes them less hazardous.

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Section: Il-mediated Preparation Of Other Energetic Compoundsmentioning

confidence: 99%

Section: Il-mediated Preparation Of Other Energetic Compoundsmentioning

confidence: 99%

Prospective Symbiosis of Green Chemistry and Energetic Materials

et al. 2017

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“…Recently, many oxadiazole (especially 1,2,5‐oxadiazole or bridged 1,2,5‐oxadiazole) based energetic materials have been reported and most of the compounds presented excellent energetic properties, thermal stabilities and sensitivities . Generally speaking, there are four oxadiazole isomers: 1,2,4‐oxadiazole, 1,2,5‐oxadiazole, 1,3,4‐oxadiazole, and 1,2,3‐oxadiazole (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Design of Energetic Materials Based on Asymmetric Oxadiazole

et al. 2019

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A new family of asymmetric oxadiazole based energetic compounds were designed. Their electronic structures, heats of formation, detonation properties and stabilities were investigated by density functional theory. The results show that all the designed compounds have high positive heats of formation ranging from 115.4 to 2122.2 kJ mol−1. −N− bridge/−N3 groups played an important role in improving heats of formation while −O− bridge/−NF2 group made more contributions to the densities of the designed compounds. Detonation properties show that some compounds have equal or higher detonation velocities than RDX, while some other have higher detonation pressures than RDX. All the designed compounds have better impact sensitivities than those of RDX and HMX and meet the criterion of thermal stability. Finally, some of the compounds were screened as the candidates of high energy density compounds with superior detonation properties and stabilities to that of HMX and their electronic properties were investigated.

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“…The high combined O + N content (69.7%), high density, and positive heat of formation of furoxan make it particularly interesting as an integral component in the construction of new HEDMs. The introduction of furoxan ring is thought to contribute to the detonation performance due to the high enthalpy of formation of the furoxan ring (∆H f o = 197.8 kJ•mol -1 ) and the presence of two active oxygen atoms in the molecule [1][2][3][4][5]. Among them, the nitrofuroxans are especially effective [6][7][8].…”

Section: Introductionmentioning

confidence: 99%

3,3′-(Diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide]

Larin

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Ферштат

et al. 2018

Molbank

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The nitramino derivatives of furoxans are of specific interest as precursors for the preparation of high energy salts with nitrogen-rich cations. In this communication, the 3,3-(diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide] was prepared via nitration of available 4,4-diamino-3,3-diazenofuroxan; the best yield of the target compound was achieved under the action of nitrating system HNO 3 /(CF 3 CO) 2 O in molar ratio 15:3 in CCl 4 at −5 • C. The structure of 3,3-(diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide] was confirmed by means of 1 H, 13 C, 14 N-NMR, IR spectroscopy and high resolution mass spectra (HRMS).

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Nitrogen‐Rich Energetic 1,2,5‐Oxadiazole‐Tetrazole – Based Energetic Materials

Abstract: An efficient o‐arylation of pivalamides by aryl iodides via rhodium(III)‐catalyzed C–H activation is demonstrated for the first time. Further, the biaryl products can be converted effectively into biologically active phenanthridine and phenanthridinone derivative.

Cited by 68 publications

References 82 publications

Prospective Symbiosis of Green Chemistry and Energetic Materials

Prospective Symbiosis of Green Chemistry and Energetic Materials

Design of Energetic Materials Based on Asymmetric Oxadiazole

3,3′-(Diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide]

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