Review on Benzofuroxan System Compounds

Wang, Nai‐Xing; Boren, Chen; Yu-xiang, OU

doi:10.1002/prep.19940190306

Cited by 24 publications

(5 citation statements)

References 30 publications

(6 reference statements)

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“…Mono-(ortho-azido)nitrobenzenes readily decompose to benzofuroxans. [55][56][57][58] This transformation was found to proceed via a concerted mechanism with a planar transition state. [59] Herein, the reaction was proven to give desired benzofuroxans unless another azido group is present in the benzene ring adjacent to the furoxan moiety (Scheme 2).…”

Section: Resultsmentioning

confidence: 95%

“…Heating of the azidonitrobenzene derivatives in ethyl acetate or DMSO leads to their degradation which rate strongly depends on the structure of the azide. Mono‐( ortho‐ azido)nitrobenzenes readily decompose to benzofuroxans [55–58] . This transformation was found to proceed via a concerted mechanism with a planar transition state [59] .…”

Section: Resultsmentioning

confidence: 99%

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Tuning Green Explosives through S_NAr Chemistry

Nikitin,

Diness

2024

Chemistry An Asian Journal

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Reactivity and regioselectivity of SNAr‐type fluorine substitution with azide in polyfluoronitrobenzenes was studied both theoretically and experimentally. The obtained polyazidonitrobenzene derivatives were extensively characterized by NMR, IR, HPLC, X‐ray, and DFT methods. It was found that the substitution with the azide nucleophile occurs first at the para‐ and the ortho‐positions to the NO2‐group and that transazidation reactions also occur here. Thermal decomposition of prepared azidonitrobenzenes was studied both in controlled (kinetic decay) and uncontrolled (explosion) modes. In case of the controlled thermal decomposition of ortho‐azidonitrobenzenes, benzofuroxans were found as major products of the reaction unless another azido group was adjacent to the furoxan moiety. The bursting power of azidonitrobenzenes was found to rise gradually with the number of the azide substituents in the aromatic ring.

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Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

Tuning Green Explosives through S_NAr Chemistry

Nikitin,

Diness

2024

Chemistry An Asian Journal

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“…An analogous furoxan compound, 4,6-dinitrobenzofuroxan were studied extensively for its ring opening reaction to its dinitroso isomer [26][27][28]. Note that one of the striking features of benzofuroxan (BFO) is its intramolecular isomerization to 1,2-dinitroso benzene intermediate to yield the starting compound eventually [29].…”

Section: Resultsmentioning

confidence: 99%

Dicyanofuroxan and Its Charged Forms - A DFT Study

Türker

2022

EJCS

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Dicyanofuroxan is a new and interesting high explosive that can be used instead of some classical explosives. The present density functional treatment considers dicyanofuroxan and its ring opened dinitroso isomer. The treatment has been based on density functional theory at the level of UB3LYP/6-311++G(d,p). Within the constraints of the theory and the basis set employed the results indicated that the ring form of dicyanofuroxan is electronically more stable and thermodynamically more favored compared to its ring-opened dinitroso isomer. Transition state geometry and energy have been obtained for the ring opening reaction of dicyanofuroxan. Furthermore its charged forms are the focus of interest. Its monoanionic and dicationic forms decompose but mono cation form undergoes some bond elongations tending to decompose. Additionally some quantum chemical properties are presented and discussed.

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“…The nitramine derivatives of benzimidazol-2-one were prepared by nitration of previously published 5-NHR-substituted 4,6-dinitro-1,3-dihydro- 2H -benzimidazol- 2-ones [ 34 ], by the application of an efficient nitration system: 40% N 2 O 5 /HNO 3 in methylene chloride medium. This system was found to be more effective and cleaner then previously used nitric and sulphuric acid mixtures [ 35 , 36 , 37 ] for the nitramine synthesis by N -nitration.…”

Section: Methodsmentioning

confidence: 92%

An Efficient Synthesis and Preliminary Investigation of Novel 1,3-Dihydro-2H-benzimidazol-2-one Nitro and Nitramino Derivatives

2022

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The preparation and properties of a series of novel 1,3-dihydro-2H-benzimidazol-2-one nitro and nitramino derivatives are described. A detailed crystal structure of one of the obtained compounds, 4,5,6-trinitro-1,3-dihydro-2H-benzimidazol-2-one (TriNBO), was characterized using low temperature single crystal X-ray diffraction, namely an orthorhombic yellow prism, space group ‘P 2 21 21’, experimental crystal density 1.767 g/cm3 (at 173K). Methyl analog, 5-Me-TriNBO-monoclinic red plates, space group, P 21/c, crystal density 1.82 g/cm3. TriNBO contains one activated nitro group at the fifth position, which was used for the nucleophilic substitution in the aminolysis reactions with three monoalkylamines (R=CH3, C2H5, (CH2)2CH3) and ethanolamine. The 5-R-aminoderivatives were further nitrated with N2O5/ HNO3 and resulted in a new group of appropriate nitramines: 1,3-dihydro-2H-5-R-N(NO2)-4,7-dinitrobenzimidazol-2-ones. Thermal analysis (TGA) of three selected representatives was performed. The new compounds possess a high melting point (200–315 °C) and thermal stability and can find a potential application as new thermostable energetic materials. Some calculated preliminary energetic characteristics show that TriNBO, 5-Me-TriNBO, 5-methylnitramino-1,3-dihydro-2H-4,7-dinitrobenzimidazol-2-one, and 5-nitratoethylnitramino-1,3-dihydro-2H-4,7-dinitrobenzimidazol-2-one possess increased energetic characteristics in comparison with TNT and tetryl. The proposed nitrocompounds may find potential applications as thermostable high-energy materials.

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Review on Benzofuroxan System Compounds

Cited by 24 publications

References 30 publications

Tuning Green Explosives through S_NAr Chemistry

Tuning Green Explosives through S_NAr Chemistry

Dicyanofuroxan and Its Charged Forms - A DFT Study

An Efficient Synthesis and Preliminary Investigation of Novel 1,3-Dihydro-2H-benzimidazol-2-one Nitro and Nitramino Derivatives

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Review on Benzofuroxan System Compounds

Cited by 24 publications

References 30 publications

Tuning Green Explosives through SNAr Chemistry

Tuning Green Explosives through SNAr Chemistry

Dicyanofuroxan and Its Charged Forms - A DFT Study

An Efficient Synthesis and Preliminary Investigation of Novel 1,3-Dihydro-2H-benzimidazol-2-one Nitro and Nitramino Derivatives

Contact Info

Product

Resources

About

Tuning Green Explosives through S_NAr Chemistry

Tuning Green Explosives through S_NAr Chemistry