Synthesis and X-Ray Crystal Structure of Bis-3,3′-(nitro- NNO-azoxy)-difurazanyl Ether

Шереметев, А. Б.; Semenov, S. E.; Кузьмин, В. С.; Strelenko, Yurii A.; Ioffe, Sema L.

doi:10.1002/(sici)1521-3765(19980615)4:6<1023::aid-chem1023>3.3.co;2-i

Cited by 10 publications

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“…Symmetrical difurazanyl ether derivatives, such as bis(3nitrofurazan-4-yl) ether, (I) (Sheremetev, 1998;, bis [3-(nitro-N,N,O-azoxy)furazan-4-yl] ether, (II) (Sheremetev, Semenov et al, 1998), and bis [3-(5H-[1,2,3]triazolo[4,5-c]furazan-5-yl)furazan-4-yl] ether, (III) (Sheremetev et al, 1999), have been developed as highly energetic materials having good explosive performance in a variety of industrial, military, and space applications. The impact and friction sensitivities of these compounds are similar to those of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX).…”

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confidence: 99%

Four 3-cyanodifurazanyl ethers: potential propellants

et al. 2003

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In earlier papers, we described the synthesis and structures of bis(3-nitrofurazan-4-yl) ether, C(4)N(6)O(7), (I), bis[3-(nitro-N,N,O-azoxy)furazan-4-yl] ether, C(4)N(10)O(9), (II), and bis[3-(5H-[1,2,3]triazolo[4,5-c]furazan-5-yl)furazan-4-yl] ether, C(8)N(14)O(5), (III). Here we compare the structures of (I)-(III) with those of four 3-cyanodifurazanyl ethers, namely bis(3-cyanofurazan-4-yl) ether, C(6)N(6)O(3), (IV), 3-cyanofurazanyl 3-nitrofurazanyl ether, C(5)N(6)O(5), (V), 3,4-bis(3-cyanofurazan-4-yloxy)furazan, C(8)N(8)O(5), (VI), and bis[3-(3-cyanofurazan-4-yloxy)furazan-4-yl]diazene, C(10)N(12)O(6), (VII). It was found that the geometric parameters of the difurazanyl ether fragments are similar in these structures and therefore not influenced by substituent effects; however, the conformation of this fragment is different, viz. structures (I), (III), (V) and (VI) have approximate C(2) symmetry, and structures (II), (IV) and (VII) have C(s) symmetry. Dense crystal packing (1.626-1.898 Mg m(-3)) is characteristic for all these hydrogen-free compounds. A linear correlation is also determined between crystal density and 'molecular density' (M/V), where M is the mass of a molecule and V is the molecular volume.

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confidence: 99%

Four 3-cyanodifurazanyl ethers: potential propellants

et al. 2003

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“…In connection with a project directed at the investigation of the nucleophilic reactions of nitrofurazans 1, 1,2 we have studied the reactivity of 1 with solid anhydrous bases in dry conditions resulting in ether bond formation and giving difurazanyl ether derivatives 2 (Scheme 1). [3][4][5][6] The yields of 2 were generally very good. A major limitation of this method is that the reaction is successful only with highly electron-withdrawing groups (R).…”

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An efficient synthesis of hydroxyfurazans

Sheremetev

Aleksandrova

1998

Mendeleev Communications

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“…A number of recent studies reported good energetic performance of novel theoretically predicted compounds bearing the N 3 O 3 group . Several energetic compounds were synthesized . It was found that the N 3 O 3 group improves the energetic parameters of compounds, such as density and enthalpy of formation, compared with the nitro group .…”

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confidence: 99%

Synthesis of New Energetic Materials Based on Furazan Rings and Nitro‐NNO‐azoxy Groups

et al. 2020

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Energetic compounds 1-6, consisting of one or two furazan rings linked by azo or azoxy bridges and one or two nitro-NNOazoxy substituents, were synthesized by nitration of the corresponding tert-butyl-NNO-azoxy precursors with NO 2 BF 4. Novel methods for the synthesis of 3,4-bis(tert-butyl-NNOazoxy)furazan (7) and bis-4,4'-(tert-butyl-NNO-azoxy)-3,3'-azoxyfurazan (21) were elaborated. The nitro-NNO-azoxy compounds obtained display high calculated detonation performance (v D = 8.07-9.40 km s À 1 and P C-J = 27.4-43.4 GPa) that is superior to the corresponding nitrofurazans (DNF, DNAzF, DNAF). The replacement of nitrofurazans with the corresponding (nitro-NNO-azoxy)furazans increases the specific impulse of the model solid composite propellant formulations by 2-10 s, which is due to high calculated heats of formation (600-892 kcal kg À 1) and positive oxygen balance (0-20 %) of the latter compounds.

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Synthesis and X-Ray Crystal Structure of Bis-3,3′-(nitro- NNO-azoxy)-difurazanyl Ether

Cited by 10 publications

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Four 3-cyanodifurazanyl ethers: potential propellants

Four 3-cyanodifurazanyl ethers: potential propellants

An efficient synthesis of hydroxyfurazans

Synthesis of New Energetic Materials Based on Furazan Rings and Nitro‐NNO‐azoxy Groups

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