General Papers ARKIVOC 2012 (ix) 62-75
2,4,6-Tris(4-methylphenyl)aniline (Table 3, entry 2). Prepared by procedure 1, and purified by column chromatography using petroleum ether/EtOAc 200/1 in 86% yield. 1H NMR: . 7.49-7.46 (m, 6H, Ph), 7.38 (s, 2H, Ph), 7.29 (d, c 8.0 Hz, 4H, Ph), 7.20 (d, J 8.0 Hz, 2H, Ph), 2.41 (s, 6H, 2.CH3), 2.37 (s, 3H, CH3), ppm; 13C NMR: . 140.07 (Ph), 138.16 (Ph), 137.13 (2.Ph), 136.81 (2.Ph), 136.01 (Ph), 131.22 (Ph), 129.65 (4.Ph), 129.47 (2.Ph), 129.30 (4.Ph), 128.40 (2.Ph),
128.13 (2.Ph), 126.34 (2.Ph), 21.19 (2.CH3), 21.11 (CH3); MS (EI) m/z: calculated value: 363.1987, found value: 363.1990 (M+); mp 113.1-114.0 °C. 2,4,6-Tris(3-methylphenyl)aniline (Table 3, entry 3). Prepared by procedure 1, and purified by column chromatography using petroleum ether/EtOAc 200/1 in 98% yield. 1H NMR: . 7.41-7.35 (m, 10H, Ph), 7.27 (t, J 7.4 Hz, 1H, Ph), 7.21-7.17 (m, 2H, Ph), 7.07 (d, J 7.2 Hz, 1H, Ph), 3.91 (s, 2H, NH2), 2.41 (s, 6H, 2.CH3), 2.37 (s, 3H, CH3), ppm; 13C NMR: . 140.99 (Ph), 140.07 (Ph), 139.77 (2.Ph), 138.70 (2.Ph), 138.31 (Ph), 131.39 (Ph), 130.22 (2.Ph), 128.94 (2.Ph), 128.75 (Ph), 128.66 (Ph), 128.39 (2.Ph), 128.29 (2.Ph), 127.36 (Ph), 127.26 (Ph), 126.48 (2.Ph), 123.67 (2.Ph), 21.70 (CH3), 21.65 (2.CH3) ppm; MS (EI) m/z: calculated value: 363.1987, found value: 363.1990 (M+); mp 96.8-97.4 °C. 2,4,6-Tris(4-methoxylphenyl)aniline (Table 3, entry 4). Prepared by procedure 1, and purified by column chromatography using petroleum ether/EtOAc 200/1 in 82% yield. 1H NMR: . 7.52
7.47 (m, 6H, Ph), 7.31 (s, 2H, Ph), 7.01 (d, J 8.8 Hz, 4H, Ph), 6.93 (d, J 8.8 Hz, 2H, Ph), 3.87 (s, 6H, 2.OCH3), 3.85 (s, 2H, NH2), 3.83 (s, 3H, OCH3), ppm; 13C NMR: . 158.92 (2.Ph), 158.47 (Ph), 140.19 (Ph), 133.68 (Ph), 132.02 (2.Ph), 130.81 (Ph), 130.49 (4.Ph), 128.00 (2.Ph), 127.80 (2.Ph), 127.45 (2.Ph), 114.30 (4.Ph), 114.14 (2.Ph), 55.36 (3.OCH3) ppm; MS (EI) m/z: calculated value: 411.1834, found value: 411.1844 (M+); mp 154.0-154.8 °C. 2,4,6-Tris(4-fluorophenyl)aniline (Table 3, entry 5). Prepared by procedure 1, and purified by column chromatography using petroleum ether/EtOAc 200/1 in 93% yield. H NMR: . 7.53-7.49 (m, 6H, Ph), 7.30 (s, 2H, Ph), 7.17 (t, J 8.8 Hz, 4H, Ph), 7.08 (t, J 8.8 Hz, 2H, Ph), 3.81 (s, 2H, NH2), ppm; 13C NMR: . 162.40 (d, JCF = 245 Hz, 2.Ph), 162.15 (d, JCF = 244 Hz, Ph), 140.52 (Ph), 136.92 (d, JCCCCF = 3 Hz, Ph), 135.40 (d, JCCCCF = 2 Hz, 2.Ph), 131.15 (d, JCCCF = 8 Hz, 4.Ph), 130.44 (Ph), 128.52 (2.Ph), 128.03 (d, JCCCF = 8 Hz, 2.Ph), 127.57 (2.Ph), 116.08 (d, JCCF = 21 Hz, 4.Ph), 115.71 (d, JCCF = 21 Hz, 2.Ph), ppm; MS (EI) m/z: calculated value: 375.1235, found value: 375.1241 (M+); mp 127.6-129.4°C. 2,4,6-Tris(3,4-difluorophenyl)aniline (Table 3, entry 6). Prepared by procedure 1, and purified by column chromatography using petroleum ether/EtOAc 200/1 in 87% yield. 1H NMR: . 7.387.16 (m, 11H, Ph), 3.87 (s, 2H, NH2), ppm; 13C NMR: . 150.55 (dd, J 248, 12 Hz, 3.Ph), 149.96 (dd, J 248, 12 Hz, 2.Ph), 149.50 (dd, J 247, 12 Hz, Ph), 140.57 (Ph), 137.48 (dd, J 6, 4 Hz, Ph), 135.84 (dd, J 6, 5 Hz, Ph), 129.33 (Ph), 128.55 (2.Ph), 126.50 (2.Ph), 125.49 (dd, J 6, 4 Hz, 2.Ph), 122.14 (dd, J 6, 4 Hz, 2.Ph), 118.41 (d, J 17 Hz, 2.Ph), 117.98 (d, J 17 Hz, 2.Ph), 117.53 (d, J 17 Hz, Ph), 115.16 (d, J 18 Hz, Ph), ppm; MS (EI) m/z: calculated value: 429.0952, found value: 429.0955 (M+); mp 194.0-194.4°C. Page 71 ©ARKAT-USA, Inc.
