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8.6 Hz), 6.82 (m, 1H), 6.77 (d, 2H, J=8.6 Hz), 6.46 (d, 1H, J=
2.0 Hz), 4.21 (d, 1H, J=10.0 Hz), 3.81 (m, 1H), 3.77 (s, 3H, OMe),
3.72 (s, 3H, OMe), 3.35 (dd, 1H, J=13.7, 7.0 Hz), 3.10 (t, 1H, J=
10.0 Hz), 2.93 ppm (dd, 1H, J=13.7, 7.0 Hz); 13C NMR (100 MHz,
CDCl3): d=159.7, 158.5, 146.5, 143.2, 140.2, 136.8, 134.3, 132.6,
131.5, 130.6, 130.3, 129.4, 128.7, 125.9, 125.5 (CF3), 124.4, 124.1,
123.2, 123.0, 122.7 (CF3), 114.0, 113.5, 110.3, 64.4, 59.3, 55.6 (OMe),
55.3 (OMe), 50.9, 40.4 ppm; IR (dry film): n˜ =1611, 1513, 1329, 1123,
801, 759 cmÀ1; UV/Vis (EtOH): lmax (log e)=275 (3.61), 227 (4.33),
202 nm (4.84); HRMS (DART): m/z calcd for C32H26F6O2+H+:
557.1915 [M+H]+; found: 557.1905.
OMe), 3.69 (s, 3H, OMe), 3.33 (td, 1H, J=11.3, 4.5 Hz), 3.19 (m, 1H),
3.23 (m, 1H), 3.09 ppm (dd, 1H, J=16.3, 4.5 Hz); 13C NMR
(100 MHz, CDCl3): d=158.1, 157.8, 141.9, 141.3, 136.3, 135.8, 135.2,
131.8, 131.3, 130.2, 129.8, 128.5, 128.0, 126.3, 113.8, 55.7, 55.2
(OMe), 55.1 (OMe), 54.6, 45.8, 39.7 ppm; IR (dry film): n˜ =1611,
1512, 830, 756 cmÀ1; UV/Vis (EtOH): lmax (log e)=287 (3.50), 257
(3.64), 225 nm (4.51); HRMS (ESI): m/z calcd for C30H26Cl2O2+K+:
527.0941 [M+K]+; found: 527.0931.
1
Dehydrotetralin 19b: light yellowish oil; H NMR (400 MHz, CDCl3):
d=7.25 (d, 2H, J=8.2 Hz), 7.22 (d, 2H, J=8.6 Hz), 7.17 (s, 1H), 7.16
(m, 4H), 7.13 (d, 2H, J=7.7 Hz), 7.07 (d, 2H, J=8.6 Hz), 6.78 (dd,
1H, J=8.2, 2.3 Hz), 6.74 (d, 2H, J=8.6 Hz), 6.52 (d, 1H, J=2.3 Hz),
4.11 (s, 2H), 3.72 (s, 3H, OMe), 3.71 ppm (s, 3H, OMe); 13C NMR
(100 MHz, CDCl3): d=159.8, 158.3, 141.0, 138.9, 136.7, 136.4, 133.8,
133.0, 132.6, 129.01, 128.99, 128.6, 128.4, 127.1, 126.7, 125.8, 115.2,
114.0, 112.8, 55.3, 55.2, 53.1, 50.8 ppm; IR (dry film): n˜ =1896, 1608,
1510, 1248, 830, 758 cmÀ1; UV/Vis (EtOH): lmax (log e)=321 (3.91),
228 nm (4.37); HRMS (DART): m/z calcd for C30H24Cl2O2+H+:
487.1232 [M+H]+; found: 487.1234.
Oxidation of 4-Methoxy-4’-nitrostilbene (18)
Oxidation of 18 (FeCl3/CH2Cl2, 1 h) gave a mixture, which on prepa-
rative radial chromatography (SiO2, hexanes/Et2O 1:1 to 100%
Et2O), gave 18b[6] (7.0 mg, 14%), 18g (5.0 mg, 10%), and 18h
(7.0 mg, 14%).
Trimer 18g: yellowish oil, and subsequently, yellowish block crystals
from MeOH; m.p. 251–2548C; 1H NMR (400 MHz, CDCl3): d=8.02
(d, 2H, J=8.6 Hz), 7.77 (m, 6H), 7.07 (d, 2H, J=8.6 Hz), 6.89 (d, 2H,
J=8.6 Hz), 6.78 (m, 5H), 6.75 (m, 2H), 6.69 (d, 2H, J=8.6 Hz), 6.38
(d, 1H, J=1.3 Hz), 4.39 (s, 1H), 4.28 (dd, 1H, J=11.5, 7.0 Hz), 4.23
(d, 1H, J=10.6 Hz), 3.81 (s, 3H, OMe), 3.73 (s, 3H, OMe), 3.71 (s,
3H, OMe), 3.47 (t, 1H, J=10.6 Hz), 3.41 (d, 1H, J=7.0 Hz),
2.78 ppm (t, 1H, J=11.5 Hz); 13C NMR (100 MHz, CDCl3): d=161.0,
158.7, 158.5, 150.4, 149.0, 147.9, 147.2, 146.6, 146.4, 145.2, 138.6,
135.0, 134.4, 133.3, 130.0, 128.5, 128.3, 123.6, 123.4, 114.3, 114.0,
113.9, 112.9, 110.0, 59.1, 58.9, 58.5, 55.6 (OMe), 55.5 (OMe), 55.3
(OMe), 53.5, 49.7, 49.0 ppm; IR (dry film): n˜ =2060, 1929, 1884,
1606, 1514, 1347 (NO2), 858, 753 cmÀ1; UV/Vis (EtOH): lmax (log e)=
277 (3.71), 201 nm (4.93); HRMS (ESI): m/z calcd for C45H37N3O9+K+:
802.2161 [M+K]+; found: 802.2156.
1
Trimer 19g: light yellowish oil; H NMR (400 MHz, CDCl3): d=7.09
(d, 2H, J=8.6 Hz), 7.07 (d, 2H, J=8.6 Hz), 6.88 (m, 4H), 6.78 (d, 4H,
J=8.6 Hz), 6.74 (d, 1H, J=1.8 Hz), 6.69 (d, 4H, J=8.6 Hz), 6.50
(brd, 4H, J=8.6 Hz), 6.34 (d, 1H, J=1.8 Hz), 4.34 (s, 1H), 4.12 (m,
1H), 4.09 (m, 1H), 3.81 (s, 3H, OMe), 3.74 (s, 3H, OMe), 3.69 (s, 3H,
OMe), 3.27 (d, 1H, J=6.8 Hz), 3.19 (t, 1H, J=10.9 Hz), 2.64 ppm (t,
1H, J=11.3 Hz); 13C NMR (100 MHz, CDCl3): d=160.4, 158.4, 158.1,
145.6, 141.7, 140.4, 139.4, 139.1, 136.1, 135.9, 134.7, 132.4, 131.6,
131.4, 130.4, 129.7, 128.5, 128.1, 128.0, 127.8, 114.1, 113.6, 112.6,
109.5, 58.7, 58.6, 58.5, 55.6 (OMe), 55.4 (OMe), 55.2 (OMe), 53.7,
49.6, 48.5 ppm; IR (dry film): n˜ =1895, 1610, 1510, 823, 752 cmÀ1
UV/Vis (EtOH): lmax (log e)=282 (3.32), 257 (3.71), 228 nm (4.30);
HRMS (DART): m/z calcd for C45H38Cl3O3+H+: 732.1965 [M+H]+;
found: 732.1954.
;
1
Indane 19h: light yellowish oil; H NMR (400 MHz, CDCl3): d=7.16
Indane 18h: yellowish oil, and subsequently, yellowish block crys-
tals from hexanes/CH2Cl2; mp 179–1818C; 1H NMR (400 MHz,
CDCl3,): d=8.02 (d, 2H, J=8.6 Hz), 8.01 (d, 2H, J=8.6 Hz), 7.23 (d,
2H, J=8.6 Hz), 7.15 (d, 2H, J=8.6 Hz), 7.01 (d, 1H, J=8.0 Hz), 6.83
(d, 2H, J=8.6 Hz), 6.78 (dd, 1H, J=8.0, 2.3 Hz), 6.76 (d, 2H, J=
8.6 Hz), 6.45 (d, 1H, J=2.3 Hz), 4.23 (d, 1H, J=9.7 Hz), 3.84 (q, 1H,
J=6.8 Hz), 3.76 (s, 3H, OMe), 3.71 (s, 3H, OMe), 3.22 (dd, 1H, J=
14.5, 6.8 Hz), 3.15 (t, 1H, J=9.7 Hz), 3.09 ppm (dd, 1H, J=14.5,
6.8 Hz); 13C NMR (100 MHz, CDCl3): d=159.9; 158.7, 150.0, 147.3,
146.8, 146.6, 146.3, 136.0, 133.9, 130.1, 129.3, 128.8, 124.3, 123.7,
123.6, 114.1, 113.8, 110.4, 64.0, 59.2, 55.6 (OMe), 55.3 (OMe), 50.8,
40.0 ppm; IR (dry film): n˜ =2046, 1926, 1798, 1608, 1515, 1347
(NO2), 831, 755 cmÀ1; UV/Vis (EtOH): lmax (log e)=278 (4.05), 223
(3.96), 204 nm (4.43); HRMS (ESI): m/z calcd for C30H26N2O6+K+:
549.1422 [M+K]+; found: 549.1439.
(d, 2H, J=8.4 Hz), 7.14 (d, 2H, J=8.2 Hz), 7.01 (d, 2H, J=8.2 Hz),
6.96 (d, 3H, J=8.4 Hz), 6.86 (d, 2H, J=8.6 Hz), 6.76 (d, 3H, J=
8.6 Hz), 6.43 (d, 1H, J=1.3 Hz), 4.18 (d, 1H, J=9.7 Hz), 3.77 (s, 3H,
OMe), 3.70 (s, 3H, OMe), 3.66 (d, 1H, J=6.8 Hz), 3.03 (d, 1H, J=
9.7 Hz), 2.98 ppm (brd, 2H, J=6.8 Hz); 13C NMR (100 MHz, CDCl3):
d=159.5, 158.4, 146.9, 140.7, 138.3, 137.1, 134.8, 132.2, 131.9,
130.7, 129.4, 128.5, 128.4, 124.4, 113.9, 113.3, 110.2, 63.4, 58.9, 55.5
(OMe), 55.3 (OMe), 51.0, 39.1 ppm; IR (dry film): n˜ =1609, 1512,
820, 757 cmÀ1; UV/Vis (EtOH): lmax (log e)=281 (3.48), 257 (3.64),
226 nm (4.39); HRMS (ESI): m/z calcd for C32H32Cl2O2+Na+:
511.1202 [M+Na]+; found: 511.1186.
Oxidation of 4-Methoxy-4’-fluorostilbene (20)
Oxidation of 20 (FeCl3/CH2Cl2, 45 min) gave a mixture, which on
preparative radial chromatography (SiO2, 2:1 hexanes/CH2Cl2 to
100% CH2Cl2), gave 20g (4.1 mg, 8%) and a mixture of 20a, 20b,
and 20h. HPLC of this mixture (Luna Phenyl-Hexyl column, 12%
H2O/MeCN to 5% H2O/MeCN in 5 min, 15 mLminÀ1) gave 20a
(1.5 mg, 3%), 20b[6] (1.5 mg, 3%), and 20h (1.5 mg, 3%).
Oxidation of 4-Methoxy-4’-chlorostilbene (19)
Oxidation of 19 (FeCl3/CH2Cl2, 1 h) gave a mixture, which on prepa-
rative radial chromatography (SiO2, hexanes/CH2Cl2 2:1 to 100%
CH2Cl2), gave 19g (3.5 mg, 7%) and a mixture of 19a, 19b, and
19h. HPLC of this mixture (C18 column, 10% H2O/MeCN,
10 mLminÀ1) gave 19a (7.5 mg, 15%), 19b (2.1 mg, 4%), and 19h
(3.0 mg, 6%).
Tetralin 20a: light yellowish oil, and subsequently, colorless block
crystals from EtOH/CH2Cl2; mp 138–1408C; 1H NMR (400 MHz,
CDCl3): d=7.09 (dd, 1H, J=8.2, 6.8 Hz), 6.98 (d, 2H, J=8.6 Hz),
6.83 (td, 1H, J=8.2, 2.3 Hz), 6.74 (d, 2H, J=8.6 Hz), 6.66 (m, 8H),
4.16 (d, 1H, J=10.4 Hz), 3.74 (s, 3H, OMe), 3.69 (s, 3H, OMe), 3.35
(td, 1H, J=11.3, 4.5 Hz), 3.21 (t, 1H, J=10.4 Hz), 3.20 (brt, 1H, J=
16.3 Hz), 3.12 ppm (dd, 1H, J=16.3, 4.5 Hz); 13C NMR (100 MHz,
CDCl3): d=162.2 (d), 159.9 (d), 158.0, 157.8, 138.5 (d), 136.6, 136.1,
132.4 (d), 130.2, 129.7 (d), 129.3 (d), 128.6, 116.2 (d), 114.7 (d), 114.2
Tetralin 19a: light yellowish oil, and subsequently, colorless block
crystals from hexanes/CH2Cl2; m.p. 209–2108C; 1H NMR (400 MHz,
CDCl3): d=7.11 (dd, 1H, J=8.2, 2.3 Hz), 7.06 (d, 1H, J=8.2 Hz), 6.98
(d, 2H, J=9.1 Hz), 6.97 (d, 2H, J=9.1 Hz), 6.94 (d, 2H, J=9.1 Hz),
6.79 (d, 1H, J=2.3 Hz), 6.74 (d, 2H, J=9.0 Hz), 6.71 (d, 2H, J=
9.1 Hz), 6.66 (d, 2H, J=9.0 Hz), 4.14 (d, 1H, J=10.3 Hz), 3.75 (s, 3H,
Chem. Asian J. 2015, 10, 2207 – 2220
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