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was added and the mixture stirred for 5 min. The solid
so obtained was filtered and recrystallized from ethyl
alcohol.
2.3. Selected data
14-(3-Fluorophenyl)-14H-dibenzo[a.j]xanthene (Table 1,
entry 3): Brown solid: mp 259 °C. IR (KBr, cmÀ1):
1
3154, 1594, 1403, 1240, 1207, 1069, 817, 747; H NMR
(300 MHz, CDCl3): d = 6.51 (s, 1H) 6.72–8.38 (m,
16H); 13C NMR (75 MHz, CDCl3): d 38.1, 113.8 and
114.0( JC–F 21.5 Hz), 115.6 and 115.9 (JC–F 21.5 Hz),
117.1, 118.2, 122.9, 124.31 and 124.34 (JC–F 2.8 Hz),
124.8, 127.4, 129.3, 129.5, 130.1 and 130.2 (JC–F
8.3 Hz), 131.5, 131.7 (JC–F 19.4 Hz), 147.8, 147.9 (JC–F
6.2 Hz), 149.2, 161.7, 165.0; EIMS, 70 eV, m/z: 376
(M+), 281, 268; Anal. Calcd for C27H17FO: C, 86.15;
H, 4.55; F, 5.05. Found: C, 86.11; H, 4.54, F, 5.07.
10. (a) Vazquez, R.; de la Fuente, M. C.; Castedo, L.;
´
Domınguez, D. Synlett 1994, 433; (b) Ishibashi, H.;
Takagaki, K.; Imada, N.; Ikeda, M. Synlett 1994, 49.
11. (a) Knight, D. W.; Little, P. B. Synlett 1998, 1141; (b)
Knight, D. W.; Little, P. B. J. Chem. Soc., Perkin Trans. 1
2001, 1771.
14-(2-Nitrophenyl)-14H-dibenzo[a.j]xanthene (Table 1,
entry 9): Yellow solid: mp 293 °C. IR (KBr, cmÀ1):
1
12. Jha, A.; Beal, J. Tetrahedron Lett. 2004, 45, 8999–9001.
13. Kuo, C.-W.; Fang, J.-M. Synth. Commun. 2001, 31, 877.
14. Papini, P.; Cimmarusti, R. Gazz. Chim. Ital. 1947, 77, 142.
15. Sen, R. N.; Sarkar, N. J. Am. Chem. Soc. 1925, 47, 1079.
16. Ota, K.; Kito, T. Bull. Chem. Soc. Jpn. 1976, 49, 1167.
17. (a) Jin, T. S.; Sun, G.; Li, Y. W.; Li, T. S. Green Chem.
2002, 4, 255; (b) Jin, T. S.; Sun, G.; Li, Y. W.; Li, T. S. J.
Chem. Res. (S) 2003, 30; (c) Jin, T. S.; Ma, Y. R.; Zhang,
Z. H.; Li, T. S. Synth. Commun. 1998, 28, 3173.
18. Chen, J.; Wu, J. Y. Specialty Petrochem. 2001, 3, 35.
19. Rhoad, M. J.; Hory, P. J. J. Am. Chem. Soc. 1950, 72,
2216.
3400, 3058, 1593, 1523, 1350, 1240, 1142, 810, 748; H
NMR (300 MHz, CDCl3): d = 7.52 (s, 1H) 7.10–8.56
(m, 16H); 13C NMR (75 MHz, CDCl3): d 32.9, 118.0,
118.4, 123.0, 124.6, 125.0, 125.3, 127.8, 128.0, 129.4,
129.5, 129.9, 130.8, 132.1, 132.6, 134.5, 141.3, 147.5,
+
149.8; EIMS, 70eV, m/z: 40 3 (M), 281, 268; Anal.
Calcd for C27H17NO3: C, 80.38; H, 4.25; N, 3.47.
Found: C, 80.25; H, 4.24, N, 3.57.
References and notes
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