Synthesis and some properties of 5-fluorodinitromethyl- and 5-difluoronitromethyltetrazoles

Фокин, А. В.; Studnev, Yu. N.; Rapkin, A. I.; Komarov, V. A.; Verenikin, O. V.; Potarina, T. M.

doi:10.1007/bf01417990

Cited by 3 publications

(7 citation statements)

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“…The synthesis of compound 4 from compound 1 was carried out according to references 26–28. Synthesis of compound 5 was performed with Selectfluor (F‐TEDA) in acetonitrile without isolation, and subsequent 1,3‐dipolar ring closure yielding compound 6 was carried out according to reference 16. Syntheses of compounds 9 and 10 were performed in anhydrous acetone.…”

Section: Resultsmentioning

confidence: 99%

“…Ammonium 5‐(fluorodinitromethyl)‐2 H ‐tetrazolate ( 6 ) was synthesised according to a slightly modified literature procedure from potassium dinitroacetonitrile ( 4 ) 16. 26–28 Differing from the literature the fluorination of potassium dinitroacetonitrile ( 4 ) was performed with Selectfluor (instead of 25 % F 2 in He) in anhydrous acetonitrile at ambient temperature in a closed vessel.…”

Section: Resultsmentioning

confidence: 99%

“…When the reaction mixture turned colourless, the solution containing compound 5 was distilled into a cooling trap (−78 °C) and compound 5 was identified by multinuclear NMR measurements from the acetonitrile solution. Subsequently, sodium azide was added to the solution and the reaction mixture was stirred at ambient temperature in a closed vessel 16. The progress of the 1,3‐dipolar ring‐closure reaction was monitored by 19 F NMR spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

“…Ammonium 5‐(fluorodinitromethyl)‐tetrazolate ( 3 ),18 potassium dinitroacetonitrile ( 4 )16, 26–28 and 2‐nitro‐azapropyl chloride ( 8 )29a were synthesised according to the literature‐known procedures and purified by re‐crystallisation (compounds 3 and 4 ) and distillation (compound 8 ).…”

Section: Methodsmentioning

confidence: 99%

“…The syntheses of 5‐trinitromethyl‐ and 5‐fluorodinitromethyl‐2 H ‐tetrazole and some of their salts were first published in 1981 by Grakauskas et al 15. and Fokin et al.,16 respectively. They used the corresponding polynitroacetonitriles17 for the 1,3‐dipolar ring‐closure reaction with trimethylsilyl azide or sodium azide.…”

Section: Introductionmentioning

confidence: 99%

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New Energetic Polynitrotetrazoles

Kettner

Klapötke

2015

Chemistry A European J

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This combined experimental, theoretical and comparative study details the syntheses and chemical characterisation of two new energetic polynitromethyl tetrazole derivatives, namely, 2-(2-nitro-2-azapropyl)-5-(trinitromethyl)-2 H-tetrazole and its fluorine-containing analogue 2-(2-nitro-2-azapropyl)-5-(fluorodinitromethyl)-2 H-tetrazole. Their crystal structures and energetic behaviour are compared to those of their starting materials, the ammonium salts of the corresponding 5-(polynitromethyl)-2 H-tetrazoles. Additionally, the crystal structures of two further related polynitrotetrazoles are presented.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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New Energetic Polynitrotetrazoles

Kettner

Klapötke

2015

Chemistry A European J

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Oxygen‐Rich 1,2,4‐Triazolo[3,4‐d]‐1,2,4‐triazolo[3,4‐f]furazano[3,4‐b]pyrazines as Energetic Materials

et al. 2016

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Oxygen-Rich 1,2,4-Triazolo [3,4-d]-1,2,4-triazolo[3,4-f]furazano [3,4b]pyrazines as Energetic Materials Aleksei B. Sheremetev,* [a] Vecheslav L. Korolev, [a] AleksandrA.P otemkin, [a, b] Abstract: Ac onvenient one-pot synthesis of 5,10-bis(trinitromethyl)-(5)a nd 5,10-bis(fluorodinitromethyl)furazano[3,4e]di([1,2,4]triazolo)[4,3-a:3',4'-c]pyrazines (6)b ye mploying the reaction of 5,6-dichlorofurazano[3,4-b]pyrazine with 5-(trinitromethyl)-and 5-(1-fluoro-1,1-dinitromethyl)tetrazoles, respectively,w as developed. The protocol was carriedo ut under mild conditions at am oderate temperature and over short reaction times to synthesize the products in excellent yields. For the first time, thesep olynitromethyl-substituted compounds, whichm ay have potential use as explosive and propellant materials,h ave been fully characterized. The burningr ate of compound 5 was shown to be slightly superior to that of 2,4,6,8,10,12-hexanitrohexaazaisowurtzitane (CL-20).[a] Prof. A. B. Sheremetev,V .L.Korolev,A .A.P otemkin, N.

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Chemistry of fluoroalkyl cyanides

Usachev¹

2020

Arkivoc

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This review is devoted to the chemistry of fluoroalkyl cyanides (R F -nitriles): their synthesis and chemical properties. Syntheses of non-functionalized R F -nitriles (FCH 2 CN, F 2 CHCN, CF 3 CN, C 2 F 5 CN, FCH 2 CH 2 CN, etc.) and dinitriles (NCCHFCN, NCCF 2 CN, NCCF 2 CF 2 CN, etc.) are considered. The synthesis of functionalized R F -nitriles such as F 2 NCF 2 CN, F 2 NCClFCN, Cl 2 CFCN, Br 2 CFCN, (O 2 N) 2 CFCN, O 2 NCF 2 CH 2 CH 2 CN, and dinitriles, such as O(CF 2 CN) 2 , NCCF 2 N=NCF 2 CN, is also considered. R F -Nitriles are attractive electrophilic, enophilic, and dienophilic building-blocks: they were used in the synthesis of various fluorine-containing heterocyclic compounds, such as R F -bearing pyridines, 1,3,5-triazines, tetrazoles, and others. R F -nitriles were also used in the synthesis of unusual acyclic compounds, such as fluoroalkylated N,N-difluoroamines, F 2 NCF 2 CF 2 N=SF 2 , R Fimino esters, and others.

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Synthesis and some properties of 5-fluorodinitromethyl- and 5-difluoronitromethyltetrazoles

Cited by 3 publications

References 2 publications

New Energetic Polynitrotetrazoles

New Energetic Polynitrotetrazoles

Oxygen‐Rich 1,2,4‐Triazolo[3,4‐d]‐1,2,4‐triazolo[3,4‐f]furazano[3,4‐b]pyrazines as Energetic Materials

Chemistry of fluoroalkyl cyanides

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