The Journal of Organic Chemistry
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127.33, 127.65, 127.66, 128.2, 129.0, 130.0, 131.0, 131.17, 131.22, 131.3,
134.2, 138.4, 138.7, 139.1, 139.8, 139.9, 140.07, 140.10, 141.2, 167.3;
HRMS m/z (Mþ) calcd for C36H26O2 490.1933, found 490.1931.
6-Formyl-1,2,3,4-tetraphenylnaphthalene (3p) (entry 11
1,2,3,4-Tetrapropylanthracene (7c) (entry 3 in Table 4):4f
mp 113ꢀ114 °C; 1H NMR (400 MHz, CDCl3) δ 1.12 (t, J = 7.3 Hz,
6H), 1.18 (t, J = 7.3 Hz, 6H), 1.67ꢀ1.58 (m, 4H), 1.83ꢀ1.73 (m, 4H),
2.80ꢀ2.75 (m, 4H), 3.17ꢀ3.13 (m, 4H), 7.97 (dd, J = 3.3, 6.6 Hz, 2H),
7.40 (dd, J = 3.3, 6.6 Hz, 2H), 8.51 (s, 2H); 13C NMR (100 MHz,
CDCl3) δ 15.0, 15.1, 24.4, 24.9, 31.5, 32.8, 122.8, 124.7, 128.2, 130.3,
130.7, 133.6, 136.6; HRMS m/z (Mþ) calcd for C26H34 346.2661, found
346.2662.
1,2,3,4-Tetraheptylanthracene (7d) (entry 4 in Table 4). oil;
1H NMR (400 MHz, CDCl3) δ 0.91 (m, 12H), 1.35ꢀ1.75 (m, 40H),
2.77ꢀ2.81 (m, 4H), 3.14ꢀ3.18 (m, 4H), 7.39ꢀ7.41 (m, 2H),
7.96ꢀ7.99 (m, 2H), 8.52 (s, 2H); 13C NMR (100 MHz, CDCl3) δ
14.14, 14.16, 22.73, 22.74, 29.1, 29.2, 29.3, 30.5, 30.6, 31.1, 31.6, 31.9,
122.8, 124.7, 128.2, 130.3, 130.7, 133.7, 136.6; HRMS m/z (Mþ) calcd
for C42H66 570.5164, found 570.5164.
in Table 3):10 mp 225ꢀ226 °C; H NMR (400 MHz, CDCl3) δ
1
6.83ꢀ6.89 (m, 10H), 7.18ꢀ7.31 (m, 10H), 7.74 (d, J = 8.7 Hz, 1H), 7.85
(d, J = 7.3 Hz, 1H), 8.14 (s, 1H), 9.95 (s, 1H); 13C NMR (100 MHz,
CDCl3) δ 122.3, 125.6, 125.7, 126.69, 126.71, 126.8, 127.0, 127.7, 127.8,
128.2, 129.0, 130.9, 131.07, 131.10, 131.14, 131.5, 133.9, 134.2, 135.0,
138.5, 138.8, 139.8, 139.9, 140.1, 140.2, 142.1, 192.5; HRMS m/z (Mþ)
calcd for C35H24O 460.1827, found 460.1826 .
5,7-Dimethyl-1,2,3,4-tetraphenylnaphthalene (3q) (entry
17 in Table 3):4i mp 252ꢀ254 °C; 1H NMR (400 MHz, CDCl3) δ
2.07 (s, 3H), 2.47 (s, 3H), 6.91ꢀ6.94 (m, 10H), 7.24ꢀ7.38 (m, 11H),
7.43 (s, 1H); 13C NMR (100 MHz, CDCl3) δ 21.5, 25.2, 124.9, 125.1,
125.2, 126.1, 126.2 (overlapped), 126.4, 126.7, 127.4, 129. 1, 131.1,
131.3, 131.4, 131.6, 132.6, 133.6, 134.88, 135.6, 137.9, 138.4, 138.5,
139.5, 140.4, 140.8 (overlapped), 143.0; HRMS m/z (Mþ) calcd for
C36H28 460.2191, found 460.2186.
1,2,3,4,5,6,7,8-Octakis(4-octylphenyl)anthracene (7e)
1
(entry 5 in Table 4). oil; H NMR (400 MHz, CDCl3) δ 0.85ꢀ
0.92 (m, 24H), 1.10ꢀ1.51 (m, 96H), 2.30ꢀ2.34 (m, 8H), 2.44ꢀ2.48
(m, 8H), 6.57ꢀ6.61 (m, 8H), 6.65ꢀ6.67 (m, 8H), 6.82ꢀ6.84 (m, 8H),
6.91ꢀ6.95 (m, 8H), 8.16 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 14.1
(overlapped), 22.7 (overlapped), 28.9, 29.4 (overlapped), 29.46, 29.48,
29.6, 31.2, 31.4, 31.96, 31.98, 35.3, 35.7, 126.4, 127.0, 130.6, 131.1, 131.3,
136.6, 138.1, 138.3, 138.5, 139.1, 140.0, 140.5; HRMS (TOF) m/z
(Mþ) calcd for C126H170 1683.3303, found 1683.3297.
5-Methyl-1,2,3,4-tetraphenylnaphthalene (3r) (entry 18
in Table 3):10 mp 237ꢀ238 °C; H NMR (400 MHz, CDCl3) δ
1
1.95 (s, 3H), 6.75ꢀ6.82 (m, 10H), 7.09ꢀ7.28 (m, 12H), 7.51ꢀ7.54 (m,
1H); 13C NMR (100 MHz, CDCl3) δ 24.3, 124.0, 124.2, 124.4, 125.1,
125.2 (overlapped), 125.3, 125.4, 125.8, 126.4, 129.3, 129.9, 130.1,
130.3, 130.4, 130.6, 132.4, 134.9, 137.0, 137.4, 138.0, 139.3, 139.4, 139.6,
139.7, 141.9; HRMS m/z (Mþ) calcd for C35H26 446.2034, found
446.2029.
1,2,3,4-Tetraphenyltetracene (8a) (entry 6 in Table 4). mp
>300 °C; 1H NMR (400 MHz, CDCl3) δ 6.82ꢀ6.91 (m, 10H), 7.25ꢀ
7.35 (m, 12H), 7.88ꢀ7.91 (m, 2H), 8.43 (s, 2H), 8.50 (s, 2H); 13C
NMR (100 MHz, CDCl3) δ 125.1, 125.4, 126.4, 126.6 (overlapped),
127.7, 128.3, 130.0, 131.1, 131.3, 131.5, 131.6, 138.0, 138.3, 139.7, 140.6;
HRMS m/z (Mþ) calcd for C42H28 532.2191, found 532.2186.
1,2,3,4-Tetrakis(4-methylphenyl)tetracene (8b) (entry 7
9,10-Diphenylphenanthrene (4) (entry 19 in Table 3):15 mp
1
235ꢀ236 °C; H NMR (400 MHz, CDCl3) δ 7.14ꢀ7.25 (m, 10H),
7.46ꢀ7.50 (m, 2H), 7.55ꢀ7.57 (m, 2H), 7.63ꢀ7.67 (m, 2H), 8.80 (d,
J = 8.4 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 122.5, 126.4, 126.5,
126.6, 127.6, 127.8, 130.0, 131.0, 131.9, 137.2, 139.6; HRMS m/z (Mþ)
calcd for C26H18 330.1409, found 330.1405.
1
in Table 4). mp 274ꢀ276 °C; H NMR (400 MHz, CDCl3) δ 2.10
(s, 6H), 2.37 (s, 6H), 6.68 (d, J = 7.8 Hz, 4H), 6.74ꢀ6.76 (m, 4H), 7.12
(d, J = 7.4 Hz, 4H), 7.18ꢀ7.20 (m, 4H), 7.30ꢀ7.32 (m, 2H), 7.85ꢀ7.88
(m, 2H), 8.39 (s, 2H), 8.46 (s, 2H); 13C NMR (100 MHz, CDCl3) δ
21.1, 21.3, 124.9, 126.5, 126.6, 127.3, 128.3, 128.4, 129.9, 131.1, 131.3,
131.37, 131.43, 134.4, 135.8, 136.9, 137.8 (overlapped), 138.6; HRMS
m/z (Mþ) calcd for C46H36 588.2817, found 588.2811.
1-Acetyl-2,3-diphenylindole (5) (entry 19 in Table 3):12b
mp 140ꢀ142 °C; 1H NMR (400 MHz, CDCl3) δ 2.00 (s, 3H),
7.21ꢀ7.43 (m, 12H), 7.43 (d, J = 7.8 Hz, 1H), 8.47 (s, 1H); 13C
NMR (100 MHz, CDCl3) δ 27.9, 116.2, 119.5, 123.3, 123.8, 125.5,
126.9, 128. 2, 128.6 (overlapped), 129.2, 130.0, 130.8, 132.9, 133.0,
135.0, 136.8, 171.6; HRMS m/z (Mþ) calcd for C22H17NO 311.1310,
found 311.1305.
1,2,3,4-Tetrakis(4-methoxyphenyl)tetracene (8c) (entry 8
in Table 4). mp >300 °C; 1H NMR (400 MHz, CDCl3) δ 3.65 (s, 6H),
3.86 (s, 6H), 6.45ꢀ6.47 (m, 4H), 6.75ꢀ6.78 (m, 4H), 6.87ꢀ6.89 (m,
4H), 7.21ꢀ7.23 (m, 4H), 7.32ꢀ7.35 (m, 2H), 7.88ꢀ7.91 (m, 2H), 8.42
(s, 2H), 8.49 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 54.8, 55.1, 112.1,
113.1, 124.9, 126.1, 126.5, 128.2, 129.9, 131.4, 131.5, 132.17, 132.20,
132.4, 133.3, 137.6, 138.5, 156.8, 157.9; HRMS m/z (Mþ) calcd for
C46H36O4 652.2614, found 652.2619.
1,2,3,4-Tetrakis(4-chlorophenyl)tetracene (8d) (entry 9 in
Table 4). mp >300 °C; 1H NMR (400 MHz, CDCl3) δ 6.77ꢀ6.79 (m,
4H), 6.92ꢀ6.94 (m, 4H), 7.21ꢀ7.24 (m, 4H), 7.34ꢀ7.39 (m, 6H),
7.92ꢀ7.93 (m, 2H), 8.34 (s, 2H), 8.52 (s, 2H); 13C NMR (100 MHz,
CDCl3) δ 125.5, 126.4, 126.7, 127.4, 128.2, 128.3, 130.0, 130.5, 131.87,
131.93, 132.2, 132.5, 133.0, 136.7, 137.5, 137.6, 138.4; HRMS m/z
(Mþ) calcd for C42H24Cl4 668.0632, found 668.0625.
8-Methyl-1,2,3,4-tetraphenyltetracene (8e) (entry 10 in
Table 4). mp 186ꢀ188 °C; 1H NMR (400 MHz, CDCl3) δ 2.48 (s,
3H), 6.84ꢀ6.90 (m, 10H), 7.16ꢀ7.19 (m, 1H), 7.26ꢀ7.35 (m, 10H),
7.62 (s, 1H), 7.80 (d, J = Hz, 1H), 8.37ꢀ8.44 (m, 4H); 13C NMR (100
MHz, CDCl3) δ 22.1, 125.3 (overlapped), 126.1, 126.3, 126.4, 126.55,
126.57 (overlapped), 127.7 (overlapped), 127.8, 127.9, 128.1, 128.2,
129.7, 130.2, 130.4, 130.7, 130.1, 131.3 (overlapped), 131.45, 131.47,
131.9, 134.7, 137.9, 138.0, 138.1, 138.2, 139.7, 140.6; HRMS m/z (Mþ)
calcd for C43H30 546.2347, found 546.2343.
5,6,7,8-Tetraphenylisoquinoline (6) (Scheme 3):16 mp
1
215ꢀ217 °C; H NMR (400 MHz, CDCl3) δ 6.82ꢀ6.90 (m, 10H),
7.17ꢀ7.28 (m, 10H), 7.43 (d, J = 6.0 Hz, 1H), 8.45 (d, J = 6.0 Hz, 1H),
9.05 (s, 1H); 13C NMR (100 MHz, CDCl3) δ 119.0, 125.7, 125.8, 126.8
(overlapped), 126.9, 127.0, 127.7, 127.8, 130.9, 131.05, 131.12, 131.2,
134.7 (overlapped), 137.37, 137.44, 138.0, 139.0, 139.4, 139.6, 140.3,
143.0 (overlapped), 151.9; HRMS m/z (Mþ) calcd for C33H23N
433.1830, found 433.1833.
1,2,3,4-Tetraphenylanthracene (7a) (entry 1 in Table 4):10
1
mp 295ꢀ296 °C; H NMR (400 MHz, CDCl3) δ 6.82 (m, 10H),
7.22ꢀ7.38 (m, 12H), 7.80ꢀ7.83 (m, 2H), 8.19 (s, 2H); 13C NMR (100
MHz, CDCl3) δ 125.3, 125.4, 125.9, 126.5, 126.6, 127.6, 128.3, 130.9,
131.3, 131.42, 131.44, 138.1, 138.5, 139.7, 140.6; HRMS m/z (Mþ)
calcd for C38H26 482.2034, found 482.2036.
6-Methoxy-1,2,3,4-tetraphenylanthracene (7b) (entry 2 in
Table 4):10 mp 284ꢀ285 °C; H NMR (400 MHz, CDCl3) δ 3.87
1
(s, 3H), 6.82ꢀ6.88 (m, 10H), 7.02ꢀ7.08 (m, 2H), 7.22ꢀ7.31 (m, 10H),
7.71 (d, J = 9.2 Hz, 1H), 8.03 (s, 1H), 8.11 (s, 1H); 13C NMR (100 MHz,
CDCl3) δ 55.2, 103.8, 120.6, 123.8, 125.25, 125.28, 125.9, 126.4, 126.47,
126.53 (overlapped), 127.59, 127.61, 128.0, 129.5, 130.0, 131.3
(overlapped), 131.36, 131.42, 131.5, 132.5, 137.5, 137.6, 138.2, 138.6,
139.8, 140.0, 140.65, 140.69, 157.3; HRMS m/z (Mþ) calcd for
C39H28O 512.2140, found 512.2134.
6,11-Dimethyl-1,2,3,4-tetraphenyltetracene (8f) (entry 11
in Table 4). mp 228ꢀ230 °C; H NMR (400 MHz, CDCl3) δ 2.92
1
2872
dx.doi.org/10.1021/jo200339w |J. Org. Chem. 2011, 76, 2867–2874