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Целинский, И. В.; Мельникова, С. Ф.; Романова, Т. В.

doi:10.1023/a:1012453012799

Cited by 46 publications

(7 citation statements)

References 5 publications

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“…After discovering the outstanding characteristics of TKX-50 as a high explosive, a different route to the precursor 5,5 0 -bistetrazole-1,1 0 -diol was necessitated. Tselinskii et al 16 reported on the synthesis of the mentioned precursor 1,1-BTO from the cyclization of diazidoglyoxime under acidic conditions for the first time. Diazidoglyoxime is prepared from dichloroglyoxime in a chloro-azido exchange reaction in DMF with more than 80 % yield, whereas dichloroglyoxime is prepared from glyoxime via chlorination in ethanol in high yield.…”

Section: Synthesis (Simple and Scalable)mentioning

confidence: 99%

Pushing the limits of energetic materials – the synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate

Fischer¹,

Fischer²,

Klapötke³

et al. 2012

J. Mater. Chem.

650

553

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The safe preparation and characterization (XRD, NMR and vibrational spectroscopy, DSC, mass spectrometry, sensitivities) of a new explosive dihydroxylammonium 5,5 0 bistetrazole 1,1 0 diolate (TKX 50) that outperforms all other commonly used explosive materials is detailed. While much publicized high performing explosives, such as octanitrocubane and CL 20, have been at the forefront of public awareness, this compound differs in that it is simple and cheap to prepare from commonly available chemicals. TKX 50 expands upon the newly exploited field of tetrazole oxide chemistry to produce a material that not only is easily prepared and exceedingly powerful, but also possesses the required thermal insensitivity, low toxicity, and safety of handling to replace the most commonly used military explosive, RDX (1,3,5 trinitro 1,3,5 triazacyclohexane). In addition, the crystal structures of the intermediates 5,5 0 bistetrazole 1,1 0 diol dihydrate, 5,5 0 bistetrazole 1,1 0 diol dimethanolate and dimethylammonium 5,5 0 bistetrazole 1,1 0 diolate were determined and presented.

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Section: Synthesis (Simple and Scalable)mentioning

confidence: 99%

Pushing the limits of energetic materials – the synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate

Fischer¹,

Fischer²,

Klapötke³

et al. 2012

J. Mater. Chem.

650

553

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show abstract

“…According to one literature procedure, 38 diazidoglyoxime 1 reacts with acetyl chloride to give 1,1'-diacetoxy-5,5'-tetrazole 5 instead of diazidoglyoxime ester 2k. However, according to another new method provided in the literature, diazidoglyoxime ester 2K was successfully obtained by reaction of diazidoglyoxime 1 and acetic anhydride.…”

Section: Resultsmentioning

confidence: 99%

New efficient synthesis of bis-1,2,4-oxadiazole derivatives via subsequent Staudinger/aza-Wittig reaction

Xie¹,

Hu²,

Li³

et al. 2022

Arkivoc

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A convenient route for the synthesis of bis-1,2,4-oxadiazoles is described. One-pot reaction of diazidoglyoxime esters and triphenylphosphine produced bis-1,2,4-oxadiazole derivatives in good overall yields by subsequent Staudinger/aza-Wittig reaction. All compounds were characterized by IR, 1 HNMR, 13 CNMR and HRMS and the structure of key product was unequivocally confirmed by X-ray diffraction analysis.

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“…For the synthesis of 1,1 0 -dihydroxy-5,5 0 -bistetrazole, see: Tselinskii et al (2001). Mo K radiation = 0.13 mm À1 T = 293 K 0.12 Â 0.11 Â 0.08 mm…”

Section: Related Literaturementioning

confidence: 99%

Bis[(diaminomethylidene)azanium] 5-(1-oxido-1H-1,2,3,4-tetrazol-5-yl)-1H-1,2,3,4-tetrazol-1-olate

Fan

2012

Acta Cryst E

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Cited by 46 publications

References 5 publications

Pushing the limits of energetic materials – the synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate

Pushing the limits of energetic materials – the synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate

New efficient synthesis of bis-1,2,4-oxadiazole derivatives via subsequent Staudinger/aza-Wittig reaction

Bis[(diaminomethylidene)azanium] 5-(1-oxido-1H-1,2,3,4-tetrazol-5-yl)-1H-1,2,3,4-tetrazol-1-olate

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