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1.
《Mendeleev Communications》2021,31(6):789-791
Novel energetic azoxy- and azofurazans bearing nitro-NNO- azoxy and amino groups were synthesized using the ammonolysis of some known (nitro-NNO-azoxy)furazans. 3-Amino-4-{[4′-(nitro-NNO-azoxy)f urazan-3′-yl]-NNO- azoxy}furazan displays the highest melting point (114 °C, decomp.) among the known (nitro-NNO-azoxy)furazans, optimal density (1.80 g cm−3), high experimental enthalpy of formation (639 kcal kg−1) and mechanical sensitivity on the level of PETN. In terms of the specific impulse level, the model solid composite propellant formulations based on this compound outperform similar formulations based on RDX, HMX or CL-20 by 7–12 s. 相似文献
2.
A. E. Frumkin A. M. Churakov Yu. A. Strelenko V. A. Tartakovsky 《Russian Chemical Bulletin》1999,48(11):2103-2107
Oxidation of one of the amino groups of 2-bromo-4,6-dichloro-1,3-phenylenediamine to the nitroso group followed by its conversion
into thetert-butyl-NNO-azoxy group afforded a derivative ofm-(tert-butyl-NNO-azoxy)aniline,viz., 2-bromo-3-(tert-butyl-NNO-azoxyl)-4,6-dichloroaniline. Analogously, the second amino group was converted into thetert-butyl-NNO-azoxy group to form a derivative of 1,3-bis(tert-butyl-NNO-azoxy)benzene,viz., 3-bromo-2,4-bis(tert-butyl-NNO-azoxyl)-1,5-dichlorobenzene The reaction of the latter with ammonia yielded 2-amino- and 2,4-diamino-substituted 1,3-bis-(tert-butyl-NNO-azoxyl)benzenes.
For Part 1, see Ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2126–2130, November, 1999. 相似文献
3.
The electrophilic substitution of thetert-butyl-NNO-azoxy group by the bromine atom was observed for the first time when 6-bromo-2,4-bis(tert-butyl-NNO-azoxy)-5-chloro-1,3-phenylenediamine was treated with bromine in AcOH. The structural factors promoting this reaction are
discussed. The direction of the replacement was confirmed by PM3 calculations of the heats of formation of intermediate cationic
σ-adducts.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2131–2134, November, 1999. 相似文献
4.
2,2-Bis(alkoxy-NNO-azoxy)propane-1,3-diols reacted with thionyl chloride to give previously unknown 5,5-bis(methoxy-NNO-azoxy)- and 5,5-bis(ethoxy-NNO-azoxy)-1,3,2-dioxathiane 2-oxides. Replacement of the hydroxy groups by chlorine is a minor reaction path. According to the
X-ray diffraction data, the heteroring in the molecule of 5,5-bis(methoxy-NNO-azoxy)-1,3,2-dioxathiane 2-oxide adopts a chair conformation with axial orientation of the S=O bond. 相似文献
5.
D. L. Lipilin A. M. Churakov Yu. A. Strelenko V. A. Tartakovsky 《Russian Chemical Bulletin》2007,56(8):1566-1568
Treatment of 2-(tert-butyl-NNO-azoxy)anilines with phosgene at 20 °C was proposed as a novel route to 1,2,4-benzotriazin-3(4H )-one 1-oxides. This method involves a new reaction, viz., an intramolecular interaction of the tert-butyl-NNO-azoxy group with a C-electrophile (leading to the formation of the N(2)—C(3) bond of the triazine ring) followed by elimination
of the tert-butyl group. Complete assignment of the signals in the 1H and 13C NMR spectra of the compounds obtained was performed.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1507–1509, August, 2007. 相似文献
6.
Hydrolysis rate of alkoxy-NNO-azoxy compounds like di(methoxy-NNO-azoxy)methane I, di-(methyl-NON-azoxy)formal II, di(methoxy-NNO-azoxy)methane III, and 2,2-di(methoxy-NNO-azoxy)propane IV in 5 M KOH solution was measured by manometric method at 80°C; rates relation is 1:40:540:10. Reversible deprotonation to
form C-anions followed by their rapid decomposition is a presumable mechanism for compounds I–III. Nucleophilic attack of OH-anion on the carbon atom of CH3ON=N(O) group is the most probable first stage of hydrolysis in the case of compound IV. 相似文献
7.
A reaction of 1,1-bis(methoxy-NNO-azoxy)ethene with nitroform at ∼20 °C gave 1,1-bis-(methoxy-NNO-azoxy)-3,3,3-trinitropropane. 相似文献
8.
Guskov A. A. Klenov M. S. Churakov A. M. Tartakovsky V. A. 《Russian Chemical Bulletin》2016,65(11):2763-2765
5-Amino-(tert-butyl-NNO-azoxy)-1,2,3,4-tetrazine 1,3-dioxide reacts with nitronium tetra-fluoroborate to give 5-amino-6-nitro-1,2,3,4-tetrazine 1,3-dioxide. This compound is of interest as a new energetic material. A plausible reaction mechanism involves electrophilic substitution of the tert-butyl-NNO-azoxy group by the nitro group.
相似文献9.
The first representative of the alkoxy-NNO-azoxy olefin series, viz., methoxy-NNO-azoxyethene, was synthesized by the pyrolysis of 1,1-bis(methoxy-NNO-azoxy)ethane. 相似文献
10.
V. P. Zelenov A. A. Voronin A. M. Churakov Yu. A. Strelenko M. I. Struchkova V. A. Tartakovsky 《Russian Chemical Bulletin》2013,62(1):117-122
3-Amino-4-(tert-butyl-NNO-azoxy)furoxan (1a) and 4-amino-3-(tert-butyl-NNO-azoxy)-furoxan (1b) and their acetyl derivatives 6a,b were obtained. The equilibria 1a ai 1b and 6a ? 6b were studied. Furoxan 6b can undergo thermal rearrangement into 3-[(tert-butyl-NNO-azoxy)(nitro)methyl]-5-methyl-1,2,4-oxadiazole (7), prolonged heating of which gives N-(2-tert-butyl-5-nitro-1-oxido-2H-1,2,3-triazol-4-yl)acetamide (8). With the transformation 7 → 8 as an example, the possibility of participation of the azoxy group in the Boulton-Katritzky rearrangements was demonstrated for the first time. 相似文献
11.
M. S. Klenov V. P. Zelenov A. M. Churakov Yu. A. Strelenko V. A. Tartakovsky 《Russian Chemical Bulletin》2011,60(10):2040-2045
A new method for the synthesis of benzotetrazine-1,3-dioxides was developed, which involves the reaction of 2-(tert-butyl-NNO-azoxy)-N-nitroanilines with the Ac2O/H2SO4 system. This method was also used for the synthesis of [1,2,5]oxadiazolo[3,4-c]cinnoline-5-oxide from 3-nitramino-4-phenylfurazan. The suggested mechanism of these reactions involves the formation of the intermediate oxodiazonium ion, resulting from acetylation of the oxygen atom of the nitramine group, followed by protonation and ionic dissociation. Then the oxodiazonium ion enters the intramolecular reaction with the neighboring tert-butyl-NNO-azoxy or phenyl group to form the corresponding heterocyclic systems. 相似文献
12.
M. S. Klenov A. M. Churakov Yu. A. Strelenko V. A. Tartakovsky 《Russian Chemical Bulletin》2011,60(10):2051-2056
A new method for the synthesis of benzotetrazine-1,3-dioxides was developed from the 2-(tert-butyl-NNO-azoxy)-N-nitroaniline O-alkyl derivatives upon the action of strong acids (H2SO4, MeSO3H, CF3CO2H) or BF3·Et2O. A mechanism suggested for these reactions includes transformation of the N=N(O)OR group (R = Me, Pri) to the oxodiazonium ion (N=N=O)+, which intramolecularly reacts with the neighboring tert-butyl-NNO-azoxy group, furnishing the tetrazine-1,3-dioxide ring. 相似文献
13.
2-Alkyl-4-amino-5-(tert-butyl-NNO-azoxy)-2H-1,2,3-triazole 1-oxides: synthesis and reduction 总被引:1,自引:0,他引:1
V. P. Zelenov A. A. Voronin A. M. Churakov Yu. A. Strelenko V. A. Tartakovsky 《Russian Chemical Bulletin》2014,63(1):123-129
A new approach to the synthesis of 4-amino-5-(tert-butyl-NNO-azoxy)-2-R-2H-1,2,3-triazole 1-oxides 1 was developed. Compounds 1 were obtained by reactions of 3-amino-4-(tert-butyl-NNO-azoxy)furoxan with aliphatic amines RNH2 (R = Me, Et, Pri, Bu, and But). 4-Amino-5-(tert-butyl-NNO-azoxy)-2-tert-butyl-2H-1,2,3-triazole 1-oxide was transformed under the action of acids into 4-amino-5-(tert-butyl-NNO-azoxy)-1-hydroxy-1H-1,2,3-triazole. Methylation of the latter with diazomethane mainly involves the O atom of the triazole oxide ring. Reduction of compounds 1 gave 4-amino-5-(tert-butyl-NNO-azoxy)-2-R-2H-1,2,3-triazoles and 4-amino-5-(tert-butyldiazenyl)-2-R-2H-1,2,3-triazoles (R = Me, Pri, and But). The structures of the compounds obtained were confirmed by 1H, 13C, and 14N NMR spectroscopy. 相似文献
14.
A. E. Frumkin A. M. Churakov Yu. A. Strelenko O. Yu. Smirnov S. L. Ioffe V. A. Tartakovsky 《Russian Chemical Bulletin》1999,48(7):1295-1298
Oxidation of 4,6-dichloro-1,3-phenylenediamine with Caro's acid yields the corresponding dinitrosobenzene, which reacts withN,N-dibromo-tert-butylamine to give 1,5-bis(tert-butyl-NNO-azoxy)-2,4-dichlorobenzene. Treatment of the latter with ammonia yields 4-amino-and 4,6-diamino-1,3-bis(tert-butyl-NNO-azoxy)benzenes.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya. No. 7, pp. 1307–1310, July, 1999. 相似文献
15.
The chemical stability of alkoxy-NNO-azoxy compounds to reduction with hydrazine hydrate has been studied. Methoxy-NNO-azoxymethane and bis(methyl-ONN-azoxy) formaldehyde acetal are more stable by orders of magnitude than bis(methoxy-NNO-azoxy)methane and 2,2-bis(methoxy-NNO-azoxy)propane. Methoxy-NNO-azoxymethane is also resistant to reduction with titanium(III) under acidic conditions and with iron(II) under basic conditions. Probable reaction mechanisms have been proposed on the basis of the substrate reactivity toward nucleophiles, acids, and alkalies. 相似文献
16.
V. P. Zelenov I. V. Fedyanin D. V. Khakimov T. S. Pivina 《Russian Chemical Bulletin》2017,66(7):1240-1249
Reactions of 3(4)-amino-4(3)-(tert-butyl-NNO-azoxy)furoxans with excess (NO2)2S2O7 or with a HNO3—H2SO4—Ac2O mixture unexpectedly produce [1,2,5]oxadiazolo[3,4-e]?[1,2,3,4]tetrazine 4,6-di-N-oxide (furazanotetrazine dioxide) and products of amino group oxidation (mainly to the corresponding azofuroxans) instead of the expected furoxanotetrazine dioxides. In some cases, individual (Z)-3,3´-((E)-diazene-1,2-diyl)-bis-((Z)-2-tert-butyl-1-oxidodiazenyl)-1,2,5-oxadiazole 2-oxide) was isolated. Formation of furazanotetrazine dioxides was observed in the reaction of 3-nitramino-4-(tert-butyl-NNO-azoxy)furoxan sodium salt with H2SO4 in Ac2O. Quantum chemical calculation at the DFT/B3LYP/6-31G(d) level of theory was used to estimate several aspects of the reactivity of 3(4)-nitramino-4(3)-(tert-butyl-NNO-azoxy)furoxans in a comparison with 3(4)-nitramino-4(3)-phenylfuroxans and the possible causes of the observed transformations were revealed. 相似文献
17.
I. N. Zyuzin 《Russian Journal of Organic Chemistry》2014,50(9):1252-1257
Chlorination of geminal bis(alkoxy-NNO-azoxy) compounds with sodium hypochlorite involves the central carbon atom and gives 1,1-bis(alkoxy-NNO-azoxy)-1-chloroalkanes with high yield. Dichlorobis-(methoxy-NNO-azoxy)methane oxidizes sodium iodide to elemental iodine. The signal from the central carbon atom in the 13C NMR spectra of bis(alkoxy-NNO-azoxy)dichloromethanes is broadened and displaced downfield relative to those of the initial compounds. 相似文献
18.
I. N. Zyuzin N. I. Golovina D. B. Lempert G. V. Shilov 《Russian Chemical Bulletin》2010,59(10):1925-1929
Reaction of bis(methoxy-NNO-azoxy)methane with formaldehyde in ethanol gives 3-ethoxy-2,2-bis(methoxy-NNO-azoxy)propan-1-ol as a minor product along with target 2,2-bis(methoxy-NNO-azoxy)ethanol. The structure of the former was confirmed by the counter synthesis and X-ray diffraction analysis. 相似文献
19.
D. L. Lipilin E. E. Karslyan A. M. Churakov Yu. A. Strelenko V. A. Tartakovsky 《Russian Chemical Bulletin》2005,54(4):1013-1020
Heating of 2-(alkyl-NNO-azoxy)-1-azidobenzenes in boiling benzene gave 2-alkyl-benzotriazole 1-oxides (Alk = Me, Et, Pri, and But). This first-order reaction involves an earlier unknown intramolecular interaction between the azido and azoxy groups with
simultaneous release of molecular nitrogen. The cyclization rate increases in the following sequence of the alkyl groups:
Me < Et < Pri < But. Complete assignment of the signals in the 1H, 13C, and 14N NMR spectra of 2-alkylbenzotriazole 1-oxides was performed.
Dedicated to Corresponding Member of the Russian Academy of Sciences E. P. Serebryakov on the occasion of his 70th birthday.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 989–996, April, 2005. 相似文献
20.
O. A. Luk’yanov G. V. Pokhvisneva T. V. Ternikova N. I. Shlykova Yu. B. Salamonov 《Russian Chemical Bulletin》2009,58(10):2063-2069
Interaction of primary amines and 2,2-dimethyl-5-nitro-5-nitroso-1,3-dioxane in the presence of dibromoisocyanurate generates
2,2-dimethyl-5-nitro-1,3-dioxan-5-yl-ONN-azoxyalkanes. Based on the reaction of the latter with AcCl/MeOH followed by further transformations, the first representatives
of mononitro- and polynitroalkyl-ONN-azoxyalkanes, i.e., (methyl-NNO-azoxy)nitromethane and dinitro(methyl-NNO-azoxy)methane, as well as some their derivatives, were prepared. 相似文献