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J.-M. Lu, M. Shi / Tetrahedron 63 (2007) 7545–7549
evaporation and the residue was purified by a flash column
chromatography.
4.1.1.5. 2-Methyl-1-(p-methylphenyl)-4-phenylnaph-
1
thalene (2e). A white solid, mp 97.7–98.5 ꢀC. H NMR
(300 MHz, CDCl3, TMS): d 2.26 (3H, s, CH3), 2.46 (3H,
s, CH3), 7.18–7.21 (2H, m, Ar), 7.28–7.55 (11H, m, Ar),
7.87–7.90 (1H, m, Ar); 13C NMR (75 MHz, CDCl3, TMS):
d 20.8, 21.3, 124.8, 125.6, 125.8, 126.5, 127.1, 128.2,
129.1, 129.7, 130.1, 130.1, 132.7, 133.4, 136.5, 136.7,
137.8, 139.3, 140.8; IR (CH2Cl2): n 3055, 3024, 2922,
2855, 1592, 1516, 1508, 1441, 1387, 1374, 819, 775, 766,
701, 532 cmꢁ1; MS (EI) m/z (%): 308 (100) [M+], 293
(15.7), 278 (6.8), 231 (1.8), 217 (1.5), 215 (9.5), 202 (2.5),
91 (1.3); HRMS (EI) Calcd for C24H20 (M+) requires
308.1565, found: 308.1559.
4.1.1.1. 2-Methyl-1,4-diphenylnaphthalene (2a). A
1
white solid, mp 129–130 ꢀC. H NMR (300 MHz, CDCl3,
TMS): d 2.27 (3H, s, CH3), 7.30–7.57 (14H, m, Ar), 7.88–
7.91 (1H, m, Ar); 13C NMR (75 MHz, CDCl3, TMS):
d 20.8, 124.8, 125.6, 125.8, 126.5, 127.0, 127.2, 128.2,
128.4, 129.7, 130.1, 130.2, 132.6, 133.3, 137.8, 139.4,
139.8, 140.8; IR (CH2Cl2): n 3056, 3025, 2920, 2859,
1591, 1496, 1441, 1387, 1373, 1072, 1030, 886, 774, 744,
702, 540 cmꢁ1; MS (EI) m/z (%): 294 (100) [M+], 279
(29.7), 217 (8.9), 215 (24.1), 202 (14.6), 77 (9.7). Anal.
Calcd for C23H18 requires C, 93.84; H, 6.16%. Found: C,
93.55; H, 6.43%.
4.1.1.6.
2-Methyl-1-(p-methoxylphenyl)-4-phenyl-
1
naphthalene (2f). A white solid, mp 120.7–121.1 ꢀC. H
NMR (300 MHz, CDCl3, TMS): d 2.27 (3H, s, CH3), 3.91
(3H, s, OCH3), 7.05–7.08 (2H, m, Ar), 7.21–7.56 (11H, m,
Ar), 7.87–7.91 (1H, m, Ar); 13C NMR (75 MHz, CDCl3,
TMS): d 20.9, 55.3, 113.8, 124.7, 125.6, 125.8, 126.5,
127.2, 128.2, 129.7, 130.1, 131.2, 131.9, 133.0, 133.6,
137.5, 139.2, 140.8, 158.6; IR (CH2Cl2): n 3062, 3032,
2953, 2925, 2834, 1609, 1515, 1508, 1441, 1386, 1373,
1243, 1035, 831, 775, 702 cmꢁ1; MS (EI) m/z (%): 324
(100) [M+], 309 (31.2), 294 (5.9), 293 (6.1), 278 (4.7), 266
(9.6), 215 (6.8), 202 (5.9), 77 (1.6); HRMS (EI) Calcd for
C24H20O (M+) requires 324.1514, found: 324.1471.
4.1.1.2.
2-Methyl-1-phenyl-4-(p-methylphenyl)-7-
methylnaphthalene (2b). A colorless oil, 1H NMR
(300 MHz, CDCl3, TMS): d 2.22 (3H, s, CH3), 2.34 (3H,
s, CH3), 2.45 (3H, s, CH3), 7.15–7.22 (2H, m, Ar), 7.28–
7.31 (5H, m, Ar), 7.40–7.53 (5H, m, Ar), 7.82 (1H, d,
J¼8.7 Hz, Ar); 13C NMR (75 MHz, CDCl3, TMS): d 20.9,
21.3, 21.8, 125.4, 125.8, 126.9, 126.9, 128.4, 128.4, 128.8,
128.9, 130.0, 130.2, 132.7, 133.4, 135.2, 136.8, 137.0,
138.0, 139.2, 140.0; IR (CH2Cl2): n 3053, 3023, 2954,
2923, 2855, 1620, 1600, 1516, 1507, 1440, 1381, 1362,
1029, 883, 824, 760, 703, 526 cmꢁ1; MS (EI) m/z (%):
322 (100) [M+], 307 (10.3), 292 (7.6), 229 (3.8), 215 (5.1),
91 (1.7); HRMS (MALDI) Calcd for C25H23 (M++H)
requires 323.1794, found: 323.1786.
4.1.1.7. 2,4-Dimethyl-1-phenylnaphthalene (2g). A
white solid, mp 75.7–76.5 ꢀC. 1H NMR (300 MHz, CDCl3,
TMS): d 2.20 (3H, s, CH3), 2.72 (3H, s, CH3), 7.23–7.51
(9H, m, Ar), 7.99 (1H, d, J¼9.0 Hz, Ar); 13C NMR
(75 MHz, CDCl3, TMS): d 19.4, 20.7, 123.9, 124.6, 125.4,
126.7, 126.8, 128.3, 129.4, 130.3, 131.0, 132.7, 133.0,
133.3, 136.5, 140.0; IR (CH2Cl2): n 3061, 3025, 2924,
2854, 1601, 1512, 1493, 1442, 1388, 1379, 1033, 874,
776, 757, 703 cmꢁ1; MS (EI) m/z (%): 232 (100) [M+],
217 (46.6), 215 (25.7), 202 (20.7), 77 (1.3); HRMS
(EI) Calcd for C18H16 (M+) requires 232.1252, found:
232.1216.
4.1.1.3. 2-Methyl-1-phenyl-4-(p-methoxylphenyl)-7-
methoxylnaphthalene (2c). A white solid, mp 135.9–
1
136.2 ꢀC. H NMR (300 MHz, CDCl3, TMS): d 2.22 (3H,
s, CH3), 3.65 (3H, s, OCH3), 3.88 (3H, s, OCH3), 6.76–
6.77 (1H, m, Ar), 6.99–7.04 (3H, m, Ar), 7.21 (1H, s, Ar),
7.30–7.33 (2H, m, Ar), 7.42–7.53 (5H, m, Ar), 7.81–7.85
(1H, m, Ar); 13C NMR (75 MHz, CDCl3, TMS): d 20.9,
55.0, 55.3, 105.3, 113.7, 116.7, 125.7, 127.0, 127.5, 127.6,
128.5, 130.1, 131.1, 133.2, 133.3, 134.6, 136.5, 139.0,
140.0, 157.3, 158.8; IR (CH2Cl2): n 3060, 2953, 2926,
2853, 2834, 1618, 1517, 1507, 1440, 1380, 1247, 1226,
1034, 833, 704, 535 cmꢁ1; MS (EI) m/z (%): 354 (100)
[M+], 339 (12.2), 324 (5.2), 309 (3.1), 293 (1.0), 277 (1.3),
202 (1.7); HRMS (EI) Calcd for C25H22O2 (M+) requires
354.1620, found: 354.1604.
4.1.1.8. 2-Ethyl-1,4-diphenylnaphthalene (2h). Awhite
solid, mp 109.7–110.6 ꢀC. 1H NMR (300 MHz, CDCl3,
TMS): d 1.13 (3H, t, J¼7.5 Hz, CH3), 2.56 (2H, q,
J¼7.5 Hz, CH2), 7.29–7.35 (4H, m, Ar), 7.40–7.57 (10H,
m, Ar), 7.89–7.92 (1H, m, Ar); 13C NMR (75 MHz,
CDCl3, TMS): d 16.0, 27.0, 124.9, 125.6, 125.8, 126.8,
127.0, 127.2, 128.2, 130.0, 130.1, 130.4, 133.4, 137.2,
138.8, 139.5, 139.8, 140.9; IR (CH2Cl2): n 3058, 3025,
2959, 2925, 2854, 1601, 1496, 1456, 1441, 1381, 1289,
1244, 891, 773, 760, 741, 701 cmꢁ1; MS (EI) m/z (%):
308 (100) [M+], 293 (15.0), 279 (8.5), 217 (1.6), 215
(20.5), 202 (4.4), 77 (1.2). Anal. Calcd for C24H20 requires
C, 93.46; H, 6.54%. Found: C, 93.07; H, 6.69%.
4.1.1.4.
2-Methyl-1-phenyl-4-(p-fluorophenyl)-7-
fluoronaphthalene (2d). A white solid, mp 95.9–96.4 ꢀC.
1H NMR (300 MHz, CDCl3, TMS): d 2.25 (3H, s, CH3),
7.05–7.29 (7H, m, Ar), 7.44–7.54 (5H, m, Ar), 7.79–7.84
(1H, m, Ar); 13C NMR (75 MHz, CDCl3, TMS): d 20.8,
110.0 (d, JC–F¼21.2 Hz), 115.0 (d, JC–F¼24.6 Hz), 115.3
(d, JC–F¼21.2 Hz), 127.2, 127.4, 128.2 (d, JC–F¼9.2 Hz),
128.6, 129.0 (d, JC–F¼1.6 Hz), 130.0, 131.5 (d, JC–F
8.0 Hz), 134.0, 134.5 (d, JC–F¼8.9 Hz), 136.4 (d, JC–F
¼
¼
4.1.1.9. 2-(2,2-Diphenylpvinyl)-3-phenyl-1H-indene
1
3.7 Hz), 137.5 (d, JC–F¼6.2 Hz), 138.4, 139.2, 160.6 (d,
JC–F¼243.4 Hz), 162.3 (d, JC–F¼244.4 Hz); IR (CH2Cl2):
n 3056, 2925, 2855, 1623, 1607, 1519, 1507, 1441, 1424,
(3a). A white solid, mp 140–141 ꢀC. H NMR (300 MHz,
CDCl3, TMS): d 2.96 (2H, s, CH2), 7.09–7.33 (12H, m,
ArH+]CH), 7.39–7.53 (8H, m, ArH); 13C NMR
(75 MHz, CDCl3): d 39.7, 120.2, 123.1, 123.4, 125.3,
126.2, 127.1, 127.6, 128.1, 128.5, 128.6, 129.8, 130.4,
135.1, 140.3, 141.0, 141.7, 142.6, 143.3, 144.7, 145.1; IR
(CH2Cl2): n 3056, 3023, 2921, 2850, 1599, 1485, 1460,
1384, 1223, 1198, 1158, 978, 834, 760, 703, 530 cmꢁ1
;
MS (EI) m/z (%): 330 (100) [M+], 315 (11.7), 295 (2.9),
235 (2.3), 233 (8.0), 220 (3.2), 215 (1.5); HRMS (EI) Calcd
for C23H16F2 (M+) requires 330.1220, found: 330.1225.