RSC Advances
Paper
0
0
ꢁ
137.7 (N-4 or N-1 ), ꢁ316.1 (NH) ppm. IR (KBr): n 3418 (m),
Notes and references
3
399 (m), 3169 (w), 1612 (s), 1562 (s), 1534 (m), 1515 (s), 1497
(
1
5
m), 1421 (s), 1403 (m), 1367 (m), 1301 (s), 1236 (w), 1211 (w),
1 (a) O. T. O'Sullivan and M. J. Zdilla, Chem. Rev., 2020, 120,
5682–5745; (b) H. Gao, Q. Zhang and J. M. Shreeve, J.
Mater. Chem. A, 2020, 8, 4193–4216; (c) D. E. Chavez, Top.
Heterocycl. Chem., 2017, 1–27.
2 (a) D. Lempert, G. Nechiporenko and G. Manelis, Cent. Eur. J.
Energ. Mater., 2011, 8, 25–38; (b) D. B. Lempert, Chin. J.
Explos. Propellants, 2015, 38, 1–7.
3 A. B. Sheremetev, V. O. Kulagina, N. S. Aleksandrova,
D. E. Dmitriev, Y. A. Strelenko, V. P. Lebedev and
Y. N. Matyushin, Propellants, Explos., Pyrotech., 1998, 23,
142–149.
4 N. E. Leonov, M. S. Klenov, O. V. Anikin, A. M. Churakov,
Y. A. Strelenko, A. A. Voronin, D. B. Lempert,
N. V. Muravyev, I. V. Fedyanin, S. E. Semenov and
V. A. Tartakovsky, ChemistrySelect, 2020, 5, 12243–12249.
5 O. V. Anikin, N. E. Leonov, M. S. Klenov, A. M. Churakov,
A. A. Voronin, A. A. Guskov, N. V. Muravyev,
Yu. A. Strelenko, I. V. Fedyanin and V. A. Tartakovsky, Eur.
J. Org. Chem., 2019, 26, 4189–4195.
ꢁ
1
+
174 (s) cm . HRMS (ESI): m/z calcd for [C H N O + Na ]:
9 6 18 8
+
17.0508; found [M + Na] : 517.0508.
0
0
N,N -Dinitro-N,N -bis{4-[(3-nitro-1H-1,2,4-triazol-1-yl)-NNO-
azoxy]-furazanyl}methanediamine (7). N (0.44 g, 4.1 mmol)
was added in one portion to a stirred solution of furazan 11
2
O
5
ꢀ
(
1.0 g, 2.0 mmol) in dry MeCN (15 mL) at ꢁ20 C under an argon
ꢀ
atmosphere. The reaction mixture was warmed to 0 C and
stirred at this temperature for 1 h. Then the reaction mixture
was concentrated under reduced pressure. The residue was
puried by preparative column chromatography (petroleum
ether/ethyl acetate, 2 : 1 to 1.5 : 1) to give furazan 7 (700 mg,
ꢀ
ꢁ1
ꢀ
5
9%) as a pale yellow solid. DSC (5 C min ): Tonset ¼ 147 C
1
(dec.). H NMR (600.1 MHz, acetone-d
6
): d 6.99 (s, 2H, CH
0.06 (s, 1H, H-5 ) ppm. H NMR (500.1 MHz, DMSO-d
2
),
0
1
1
6
): d 6.84
0
13
(s, 2H, CO ), 10.16 (s, 1H, H-5 ) ppm. C NMR (125.8 MHz,
2
0
DMSO-d ): d 64.9 (CH ), 145.3 (C-3), 145.5 (C-5 ), 153.9 (C-4),
1
d 64.9 (t, CH
6
2
0
59.6 (C-3 ) ppm. C NMR ([GATED], 125.8 MHz, DMSO-d ):
6
13
1
0
1
2
, JC,H ¼ 165.1 Hz), 145.3 (C-3), 145.5 (d, C-5 , JC,H
0
3 14
¼
240.4 Hz), 154.0 (C-4), 159.6 (d, C-3 , JC,H ¼ 14.4 Hz).
NMR (43.4 MHz, acetone-d , Dn1/2 ¼ 120 Hz);
): d ꢁ31 (C–NO
44 (N–NO
N
6 (a) O. A. Luk'yanov, G. V. Pokhvisneva, T. V. Ternikova,
N. I. Shlykova and M. E. Shagaeva, Russ. Chem. Bull., 2011,
60, 1703–1711; (b) O. A. Luk'yanov and V. V. Parakhin,
Russ. Chem. Bull., 2012, 61, 1582–1590.
6
2
ꢁ
2
, Dn1/2 ¼ 100 Hz), ꢁ83 [N(O)]N, Dn1/2 ¼ 260
15
Hz] ppm. N NMR ([INVGATED], 50.7 MHz, DMSO-d
6
): d 40.9,
3
6.4 (furazan rings), ꢁ30.1 (C–NO ), ꢁ42.7 (N–NO ), ꢁ53.4
7 M. S. Klenov, A. A. Guskov, O. V. Anikin, A. M. Churakov,
Y. A. Strelenko, I. V. Fedyanin, K. A. Lyssenko and
V. A. Tartakovsky, Angew. Chem., Int. Ed., 2016, 55, 11472–
11475; Angew. Chem., 2016, 128, 11644–11647.
8 A. A. Konnov, M. S. Klenov, A. M. Churakov, Yu. A. Strelenko,
A. O. Dmitrienko, L. N. Puntus, K. A. Lyssenko and
V. A. Tartakovsky, Asian J. Org. Chem., 2018, 7, 2534–2545.
2
2
0
0
0
[
N(O)]N], ꢁ82.3 [N(O)]N], ꢁ92.0 (N-2 ), ꢁ135.4 (N-1 or N-4 ),
0
0
ꢁ
137.0 (N-4 or N-1 ), ꢁ208.2 (N–NO ) ppm. IR (KBr): n 3178 (w),
2
1
609 (s), 1566 (s), 1520 (m), 1425 (m), 1376 (w), 1285 (s), 1245
ꢁ
1
(w), 1179 (w) cm . HRMS (ESI): m/z calcd for [C
9
H
4
N
20
O
12
+
+
+
4 4
NH ]: 602.0656; found [M + NH ] : 602.0654.
9
H. Wei, H. Gao and J. M. Shreeve, Chem.–Eur. J., 2014, 20,
6943–16952.
1
Conflicts of interest
1
0 D. E. Chavez, D. A. Parrish, L. Mitchell and G. H. Imler,
Angew. Chem., Int. Ed., 2017, 56, 3575–3580; Angew. Chem.,
There are no conicts to declare.
2017, 129, 3629–3632.
1
1
1 A. Gunasekaran, M. L. Trudell and J. H. Boyer, Heteroat.
Chem., 1994, 5, 441–446.
2 N. Fischer, K. H u¨ ll, T. M. Klap ¨o tke, J. Stierstorfer, G. Laus,
Acknowledgements
M.
H. Schottenberger, Dalton Trans., 2012, 41, 11201–11211.
Foundation (Project No. 19-13-00276) with the exception of the 13 R. M. Moriarty, T. E. Hopkins, I. Prakash, B. K. Vaid and
X-ray structural studies, the study of thermal stability and
R. K. Vaid, Synth. Commun., 1990, 20, 2353–2357.
sensitivity of compounds, thermochemical studies and the 14 S. E. Semenov, A. M. Churakov, L. F. Chertanova,
Hummel,
C.
Froschauer,
K.
Wurst
and
This work was nancially supported by the Russian Science
calculations of energetic properties of compositions. I. V.
Fedyanin thanks the Center for molecule composition studies
Yu. A. Strelenko, S. L. Ioffe and V. A. Tartakovskii, Russ.
Chem. Bull., 1992, 41, 277–279.
of INEOS RAS for the nancial support of the X-ray structural 15 X. Zhao, C. Qi, L. Zhang, Y. Wang, S. Li, F. Zhao and S. Pang,
studies. E. K. Kosareva thanks the grant (state task 0082-2018-
Molecules, 2014, 19, 896–910.
002, AAAA-A18-118031490034-6) for the nancial support of 16 V. M. Vinogradov, I. L. Dalinger, V. I. Gulevskaya and
0
the study of thermal stability and sensitivity of compounds. T. S.
S. A. Shevelev, Russ. Chem. Bull., 1993, 42, 1369–1371.
Kon'kova and Y. N. Matyushin thank the grant (state task 0082- 17 A. M. Churakov, S. E. Semenov, S. L. Ioffe, Y. A. Strelenko and
019-0006, AAAA-A21-121011990037-8) for the nancial support
V. A. Tartakovskii, Mendeleev Commun., 1995, 102–103.
of thermochemical studies. D. B. Lempert thanks the grant 18 X-ray data for compound 4: sp. gr. P2 2 2 , a ¼ 4.8786(8), b ¼
2
1
1 1
3
0
(
state task 0089-2019-0005, AAAA-A19-119101690058-9) for the
nancial support of the calculations of energetic properties of
compositions.
7.9416(13), c ¼ 22.587(4) A˚ , V ¼ 875.1(2) A˚ , Z ¼ 4 (Z ¼ 1), R
1
¼ 0.0415 (for 1987 rens with I > 2s(I)), wR ¼ 0.0875, GOF ¼
2
24020 | RSC Adv., 2021, 11, 24013–24021
© 2021 The Author(s). Published by the Royal Society of Chemistry