924
J. Wei et al.
817s, 516m. dH (300MHz, CDCl3) 8.90 (2H, s, ArH), 7.57 (2H,
d, J 8.4, ArH), 7.38 (3H, dd, J1 8.4, J2 7.8 Hz), 6.74 (2H, d, J
16.8, vinylic CH). dC (75 MHz, CDCl3) 150.11, 145.99, 137.34,
133.58, 133.45, 132.15, 128.79, 124.30, 122.21, 117.12. Anal.
Calc. for C14H8BrN3O6 (392.96): C 42.66, H 2.05, N 10.66.
Found: C 42.62, H 1.91, N 10.57 %.
DMSO-d6) 140.88, 139.67, 136.31, 134.31, 134.09, 133.90,
130.71, 129.94, 128.10, 126.28, 126.02, 120.98. m/z (ESI)
580.89 [M ꢀ H]ꢀ. Anal. Calc. for C22H14N8O12 (582.07): C
45.37, H 2.42, N 19.24. Found: C 45.30, H 2.32, N 19.21 %.
1,3,5-Tris(2,4,6-trinitrostyryl)benzene[5] (15C)
Yield: 90.3 %, yellow crystals. nmax (KBr)/cmꢀ1 3094s,
1606s, 1564s, 1515s, 1346s, 1174m, 970s, 918s. dH (300 MHz,
CDCl3) 8.97 (6H, s, ArH), 7.57 (3H, s, ArH), 7.50 (3H, d, J 17.4,
vinylic CH), 6.82 (3H, d, J 17.4, vinylic CH); Anal. Calc. for
C30H15N9O18 (789.05): C 45.64, H 1.92, N 15.97. Found: C
45.60, H 1.81, N 15.94 %.
(E)-3-Amino-40-bromo-2,4,6-trinitrostilbene (11C)
Yield: 82.8 %, mp 2388C, yellow crystals. nmax (KBr)/cmꢀ1
3456s, 3351s, 1622s, 1579s, 1543s, 1528s, 1491m, 1341s,
1276s, 974m, 812m, 493w. dH (500 MHz, CDCl3) 9.20 (1H, s,
ArH), 7.54 (2H, d, J 8.5, ArH), 7.37 (3H, m), 6.62 (1H, d, J 16.5,
vinylic CH). m/z (ESI) 407 [M – H]ꢀ. Anal. Calc. for
C14H9BrN4O6 (407.97): C 41.10, H 2.22, N 13.69. Found: C
41.07, H 2.10, N 13.61 %.
3,30,300-(1E,10E,100E)-2,20,200-(Benzene-1,3,5-triyl)tris
(ethene-2,1-diyl)tris(2,4,6-trinitroaniline) (15D)
Yield: 96 %, orange solid. nmax (KBr)/cmꢀ1 3464m, 3359s,
1624s, 1579s, 1526s, 1333s, 1284s, 966m, 893w. dH (300 MHz,
DMSO-d6) 8.95 (3H, s, ArH), 8.41 (6H, s, NH2), 7.78 (3H, s,
ArH), 7.62 (3H, d, J 16.5, vinylic CH), 6.75 (3H, d, J 16.5,
vinylic CH). dC (75MHz, DMSO-d6) 140.92, 139.66, 136.95,
134.18, 134.09, 130.80, 128.68, 126.46, 126.34, 121.72. m/z
(ESI) 832.69 [M ꢀ H]ꢀ. Anal. Calc. for C30H18N12O18 (834.09):
C 43.18, H 2.17, N 20.14. Found: C 43.12, H 2.09, N 20.10 %.
(E)-3-Amino-40-methyl-2,4,6-trinitrostilbene (12C)
Yield: 93.8 %; mp 2298C; orange crystals. nmax (KBr)/cmꢀ1
3456s, 3351s, 1621s, 1578s, 1543s, 1428m, 1339s, 1280s,
979m, 808m. dH (500 MHz, CDCl3) 9.18 (1H, s, ArH), 7.38
(2H, d, J 8.5, ArH), 7.33 (1H, d, J 16.5, vinylic CH), 7.21 (2H, d,
J 8.0, ArH), 6.69 (1H, d, J 16.5, vinylic CH), 2.385 (3H, s, CH3).
m/z (ESI) 343 [M ꢀ H]ꢀ. Anal. Calc. for C15H12N4O6 (344.08):
C 52.33, H 3.51, N 16.27. Found: C 52.30, H 3.44, N 16.24 %.
X-Ray Crystallographic Analysis of 13D
1,4-Bis(2,4,6-trinitrostyryl)benzene[5] (13C)
Orange crystals of C22H14N8O12 with wavelength of 0.71073,
˚
Yield: 95.1 %, yellow crystals. nmax (KBr)/cmꢀ1 3085s,
1598s, 1566s, 1504s, 1367s, 1315s, 1198m, 970s, 812s. dH
(300 MHz, DMSO-d6) 9.12 (4H, s, ArH), 7.66 (4H, s, ArH),
7.59 (2H, d, J 16.5, vinylic CH), 6.85 (2H, d, J 16.5, vinylic CH).
Anal. Calc. for C22H12N6O12 (552.05): C 47.84, H 2.19,
N 15.21. Found: C 47.80, H 2.12, N 15.15 %.
˚
˚
P21/c, a 6.608(2) A, b 27.208(9) A, c 9.503(3) A, V 1644.1
3
(9) A , Z 2, Dx 1.472 g cmꢀ3. Correction method was MULTI-
˚
SCAN, final R indicates R1 0.0642, wR2 0.1590. Crystallo-
graphic data for 13D have been deposited in the Cambridge
Crystallographic Data Centre with the deposition number
1004138. Copies of the data can be obtained, free of charge,
on application to the Director, CCDC, 12 Union Road,
Cambridge CB2 1EZ, UK (fax: þ44-(0)1223-336033, email:
3,30-(1E,10E)-2,20-(1,4-Phenylene)bis(ethane-2,1-diyl)bis
(2,4,6-trinitroaniline) (13D)
Yield: 93.2 %, orange crystals. nmax (KBr)/cmꢀ1 3480m,
3361s, 1614s, 1571s, 1536s, 1508s, 1328s, 1284s, 977m,
813m. dH (300 MHz, DMSO-d6) 8.96 (2H, s, ArH), 8.41 (4H,
s, NH2), 7.62 (4H, s, ArH), 7.50 (2H, d, J 16.5, vinylic CH), 6.74
(2H, d, J 16.5, vinylic CH). dC (75 MHz, DMSO-d6) 140.89,
139.66, 136.44, 134.34, 134.09, 133.79, 130.68, 128.01,
126.27, 120.95. m/z (ESI) 580.82 [M ꢀ H]ꢀ. Anal. Calc. for
C22H14N8O12 (582.07): C 45.37, H 2.42, N 19.24. Found: C
45.33, H 2.37, N 19.23 %.
Supplementary Material
1H and 13C NMR, mass spectrometry, and differential scanning
calorimetry spectra are available on the Journal’s website.
Acknowledgements
This project was funded by the Priority Academic Program Development of
Jiangsu Higher Education Institutions (PAPD).
1,3-Bis(2,4,6-trinitrostyryl)benzene[5] (14C)
References
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[3] K. G. Shipp, L. A. Kaplan, M. E. Sitzmann, J. Org. Chem. 1972, 37,
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[5] Z. G. Feng, B. R. Chen, Propellants, Explos., Pyrotech. 1991, 16, 12.
Yield: 89.5 %, mp 241.58C, yellow crystals. nmax (KBr)/
cmꢀ1 3080m, 1602s, 1534s, 1403m, 1346s, 917m, 798m,
725m. dH (300 MHz, DMSO-d6) 9.14 (4H, s, ArH), 7.84 (1H,
s, ArH), 7.66 (3H, dd, J1 7.5, J2 3.9, ArH), 7.57 (2H, d, J 16.8,
vinylic CH), 6.88 (2H, d, J 16.8, vinylic CH). Anal. Calc. for
C22H12N6O12 (552.05): C 47.84, H 2.19, N 15.21. Found:
C 47.81, H 2.12, N 15.18 %.
3,30-(1E,10E)-2,20-(1,3-Phenylene bis(ethene-2,1-diyl)
bis(2,4,6-trinitroaniline) (14D)
[6] Z. G. Feng, B. R. Chen, Propellants, Explos., Pyrotech. 1992, 17, 237.
[7] X. H. Peng, T. Y. Chen, C. X. Lu, R. K. Sun, Org. Prep. Proced. Int.
[8] K. K. Kalninsh, A. D. Kutsenko, A. S. Archegova, J. Struct. Chem.
[9] L. Q. Wang, Y. H. Liu, T. L. Zhang, Chin. J. Chem. 2007, 25, 1044.
Yield: 95.7 %, mp 2728C, orange solid. nmax (KBr)/cmꢀ1
3446m, 3345s, 1619s, 1578s, 1536s, 1429m, 1332s, 1283s,
964w, 793m. dH (300 MHz, DMSO-d6) 8.97 (2H, s, ArH),
8.42 (4H, s, NH2), 7.77 (1H, s, ArH), 7.60 (2H, d, J 7.5, ArH),
7.54 (3H, m), 6.75 (2H, d, J 16.5, vinylic CH). dC (75 MHz,