Recent Advanced Strategies for Extending the Nitrogen Chain in the Synthesis of High Nitrogen Compounds

Yongxing Tang; Hongwei Yang; Guangbin Cheng

doi:10.1055/s-0033-1339854

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(17): 2183-2187
DOI: 10.1055/s-0033-1339854

synpacts

Recent Advanced Strategies for Extending the Nitrogen Chain in the Synthesis of High Nitrogen Compounds

Authors

Yongxing Tang

School of Chemical Engineering, Nanjing University of Science and Technology, Xiaolingwei 200, Nanjing, Jiangsu, P. R. of China Fax: +86(25)84303286 eMail: hyang@mail.njust.edu.cn eMail: gcheng@mail.njust.edu.cn
Hongwei Yang*

School of Chemical Engineering, Nanjing University of Science and Technology, Xiaolingwei 200, Nanjing, Jiangsu, P. R. of China Fax: +86(25)84303286 eMail: hyang@mail.njust.edu.cn eMail: gcheng@mail.njust.edu.cn
Guangbin Cheng*

School of Chemical Engineering, Nanjing University of Science and Technology, Xiaolingwei 200, Nanjing, Jiangsu, P. R. of China Fax: +86(25)84303286 eMail: hyang@mail.njust.edu.cn eMail: gcheng@mail.njust.edu.cn

Abstract

Alle Artikel dieser Rubrik

Abstract

The synthesis and handling of compounds containing long catenated nitrogen chains are challenging for researchers in this field. These challenges arise from their high endothermic, thermodynamic instability, and a serious lack of nitrogen–nitrogen bond-forming reactions. This paper addresses techniques of azo-coupling reaction between the diazonium salt of N-NH₂ and amine derivative to form the longest nitrogen chain (N₁₁). This type of nitrogen–nitrogen bond formation opens a new strategy for the construction of novel compounds containing odd or even numbers of catenated nitrogen atoms (≥9) especially for polynitrogen compounds.

Key words

azo coupling - energetic materials - catenated nitrogen-atom chain - formation of nitrogen–nitrogen bond - tetrazole

Volltext

Referenzen

References and Notes

1a Zhang YQ, Parrish DA, Shreeve JM. Chem. Eur. J. 2012; 18: 987
1b Sabatini JJ, Raab JM, Hann JrR. K, Damavarapu R, Klapötke TM. Chem. Asian J. 2012; 7: 1657
1c Sabatini JJ, Nagori AV, Chen G, Chu P, Damavarapu R, Klapötke TM. Chem. Eur. J. 2012; 18: 628
1d Kumar AS, Ghule VD, Subrahmanyam S, Sahoo AK. Chem. Eur. J. 2013; 19: 509
1e Tao GH, Parrish DA, Shreeve JM. Inorg. Chem. 2012; 51: 5305
1f Steinhauser G, Giester G, Wagner C, Weinberger P, Zachhuber B, Ramer G, Villa M, Lendl B. Inorg. Chem. 2012; 51: 6739
1g Joo YH, Gao HX, Parrish DA, Cho SG, Goh EM, Shreeve JM. J. Mater. Chem. 2012; 22: 6123
1h Fu Z, Su R, Wang Y, Wang YF, Zeng W, Xiao N, Wu YK, Zhou ZM, Chen J, Chen FX. Chem. Eur. J. 2012; 18: 1886
1i Fischer N, Izsák D, Klapötke TM, Rappenglück S, Stierstorfer J. Chem. Eur. J. 2012; 18: 4051
1j Cooper PW. Explosives Engineering . VCH; Weinheim: 1996

2a Christe KO. Propellants Explos. Pyrotech. 2007; 32: 194
2b Huynh MV, Hiskey MA, Hartline EL, Montoya DP, Gilardi R. Angew. Chem. Int. Ed. 2004; 116: 5032
2c Christe KO, Wilson WW, Sheehy JA, Boatz JA. Angew. Chem. In. Ed. 1999; 38: 2004
2d Klapötke TM, Martin FA, Stierstorfer J. Angew. Chem. Int. Ed. 2011; 50: 4227

3a Li YC, Qi C, Li SH, Zhang HJ, Sun CH, Yu YZ, Pang SP. J. Am. Chem. Soc. 2010; 132: 12172
3b Li YC, Li SH, Qi C, Zhang HJ, Zhu MY, Pang SP. Acta Chim. Sinica 2011; 18: 2159
3c Klapötke TM, Piercey DG. Inorg. Chem. 2011; 50: 2732
3d Klapötke TM, Piercey DG, Stierstorfer J. Dalton Trans. 2012; 41: 9451
3e Tang YX, Yang HW, Shen JH, Wu B, Ju XH, Lu CX, Cheng GB. New J. Chem. 2012; 36: 2447

4 Ohsawa A, Arai H, Ohnishi H, Itoh T, Kaihoh T, Okada M, Igeta H. J. Org. Chem. 1985; 50: 5520
5 Salazar L, Espada M, Avendańo C, Elguero J. J. Heterocycl. Chem. 1990; 27: 1109
6 Raap R. Can. J. Chem. 1969; 47: 3677
7 Tamura Y, Minamikawa J, Sumoto K, Fujii S, Ikeda M. J. Org. Chem. 1973; 38: 1239
8 Herve G, Roussel C, Graindorge H. Angew. Chem. Int. Ed. 2010; 49: 3177

9a Klapötke TM, Petermayer C, Piercey DG, Stierstorfer J. J. Am. Chem. Soc. 2012; 134: 20827
9b Klapötke TM, Piercey DG, Stierstorfer J. Eur. J. Inorg. Chem. 2013; 1509
9c Klapötke TM, Piercey DG, Stierstorfer J. Eur. J. Inorg. Chem. 2012; 5694

10a Zhang YQ, Parrish DA, Shreeve JM. J. Mater. Chem. A 2013; 1: 585
10b He CL, Zhang JH, Parrish DA, Shreeve JM. J. Mater. Chem. A 2013; 1: 2863

11a Thottempudi V, Forohor F, Parrish DA, Shreeve JM. Angew. Chem. 2012; 124: 10019
11b Gao HX, Ye C, Gupta OD, Xiao JC, Hiskey MA, Twamley B, Shreeve JM. Chem. Eur. J. 2007; 13: 3853

12 Klapötke TM, Martin FA, Stierstorfer J. Chem. Eur. J. 2012; 18: 1487
13 Liu L, He CL, Li CS, Li ZX. J. Chem. Crystallogr. 2012; 42: 816

14a Christe KO, Wilson WW, Sheehy JA, Boatz JA. Angew. Chem. Int. Ed. 1999; 38: 2004
14b Vij A, Wilson WW, Vij V, Tham FS, Sheehy JA, Christe KO. J. Am. Chem. Soc. 2001; 123: 6308

15 Wilson WW, Haiges R, Boatz JA, Christe KO. Angew. Chem. Int. Ed. 2007; 46: 3023
16 Christe KO, Haiges R, Wilson WW, Boatz JA. Inorg. Chem. 2010; 49: 1245
17 Tang YX, Yang HW, Wu B, Ju XH, Lu CX, Cheng GB. Angew. Chem. Int. Ed. 2013; 52: 4875
18 Taha MA. M. J. Indian Chem. Soc. 2005; 82: 172
19 Gaponik PN, Karavai VP. Chem. Heterocycl. Compd. 1984; 20: 1388
20 Klapötke TM, Minar NK, Stierstorfer J. Polyhedron 2009; 28: 13
21 Typical Procedure A solution of NaNO₂ (0.69 g, 10 mmol) in H₂O (5 mL) was added dropwise to a stirring solution of DAT (1.0 g, 10 mmol) in concd HCl (5 mL). The reaction mixture was kept at 0 °C for 30 min. The crude residues obtained after the removal of the solvent under vacuum was treated with hot EtOH (20 mL) and then filtered to remove unsolvable salt. The filtrate was evaporated, dried, and recrystallized with EtOH to afford 0.5 g of needle crystals. ¹H NMR (500 MHz, DMSO-d ₆, 25 °C, TMS): δ = 7.93 ppm. ¹³C NMR (126 MHz, DMSO-d ₆, 25 °C, TMS): δ = 153.8, 152.5, 150.1 ppm. IR: 3403 (m), 3193 (m), 3157 (m), 3056 (s), 1692 (s), 1640 (vs), 1578 (w), 1472 (vw), 1447 (w), 1274 (w), 1052 (w), 984 (w), 893 (w), 773 (w), 728 (w), 673 (w) cm^–1. Raman: 1684, 1582, 1390, 1284, 1062, 746 cm^–1. BAM impact: 10 J; BAM friction: 160 N; electrostatic sensitivity discharge (ESD): 0.32 J.