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(S,E)-1-(4-Fluorophenylsulfinyl)-2-styrylbenzene (5c). Following
the similar procedure with 1,2:5,6-di-O-isopropylidene-a-D-glucofur-
anosyl (S)-4-fluorophenylsulfinate13 in place of (S)-(L)-menthyl
2-methoxy-1-naphthalensulfinate. Colorless oil: 0.84 g, 52% yield; Rf =
111.0, 56.8, 55.6; 19F NMR (377 MHz, CDCl3) δ −113.96 (s, 1F);
HRMS (ESI, m/z) calcd for C26H21FO3SNa [M + Na]+ 455.1093,
found 455.1089.
(R,E)-1-(3,4-Dimethoxy-2-(4-methoxystyryl)phenylsulfinyl)-2-me-
0.31 (petroleum ether/ethyl acetate = 4/1); [α]20 = +45.6 (c = 1.3,
thoxynaphthalene (5j). White solid: 1.28 g, 54% yield; mp 60−62 °C;
D
Rf = 0.22 (petroleum ether/ethyl acetate = 1/1); [α]26 = −101.1
1
CHCl3); H NMR (400 MHz, CDCl3) δ 8.03−7.93 (m, 1H), 7.68−
D
(c = 1.0, CHCl3); 1H NMR (400 MHz, CDCl3) δ 8.61 (d, J = 8.5 Hz,
1H), 8.08 (d, J = 8.8 Hz, 1H), 7.83 (d, J = 9.1 Hz, 1H), 7.70 (d, J =
7.5 Hz, 1H), 7.38−7.25 (m, 2H), 7.06 (d, J = 8.8 Hz, 1H), 7.04−6.97
(m, 3H), 6.88 (d, J = 16.3 Hz, 1H), 6.76 (t, J = 5.7 Hz, 2H), 6.49 (d,
J = 16.3 Hz, 1H), 3.92 (s, 3H), 3.81 (s, 3H), 3.65 (s, 3H), 3.61 (s,
3H); 13C NMR (100 MHz, CDCl3) δ 159.5, 157.5, 154.3, 146.9,
135.4, 134.7, 134.3, 132.3, 130.2, 130.1, 129.3, 128.6, 128.1, 128.0,
124.3, 123.1, 123.0, 120.5, 117.9, 113.9, 113.1, 110.2, 60.2, 56.4, 56.1,
55.5; HRMS (ESI, m/z) calcd for C28H26O5SNa [M + Na]+ 497.1399,
found 497.1408.
7.61 (m, 1H), 7.61−7.44 (m, 7H), 7.40 (t, J = 7.4 Hz, 2H), 7.32 (t, J =
7.3 Hz, 1H), 7.12−6.94 (m, 3H);13C NMR (101 MHz, CDCl3) δ
165.6, 136.6, 136.2, 133.0, 131.5, 129.0, 128.8, 128.7, 127.6, 127.5,
126.9, 126.4, 124.6, 122.9, 116.8, 116.6; 19F NMR (377 MHz, CDCl3)
δ −109.03 (s, 1F); HRMS (ESI, m/z) calcd for C20H15FOSNa [M +
Na]+ 345.0725, found 345.0737.
(S,E)-1-(4-Methoxyphenylsulfinyl)-2-styrylbenzene (5d). Following
the similar procedure with (S)-(L) menthyl p-methoxybenzenesulfi-
nate14 in place of (S)-(L)-menthyl 2-methoxy-1-naphthalensulfinate.
White solid: 0.77 g, 46% yield; mp 101−103 °C; Rf = 0.29 (petroleum
1
ether/ethyl acetate = 2/1); [α]25 = −326.6 (c = 0.6, CHCl3); H
(R,E)-1-(2-(4-Fluorostyryl)-3,4-dimethoxyphenylsulfinyl)-2-methoxy-
D
naphthalene (5k). White solid: 1.45 g, 63% yield; mp 76−78 °C; Rf =
NMR (400 MHz, CDCl3) δ 8.11−8.01 (m, 1H), 7.68−7.58 (m, 1H),
7.54−7.49 (m, 2H), 7.46 (dd, J = 10.0, 6.5 Hz, 5H), 7.38 (t, J = 7.5 Hz,
2H), 7.31 (t, J = 7.2 Hz, 1H), 6.97 (d, J = 16.0 Hz, 1H), 6.91−6.83 (m,
2H), 3.75 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 161.9, 143.1,
136.7, 136.5, 135.9, 132.5, 131.1, 129.0, 128.7, 128.5, 127.6, 126.9,
126.2, 124.4, 123.1, 114.9, 55.6; HRMS (ESI, m/z) calcd for
C21H18O2SNa [M + Na]+ 357.0925, found 357.0919.
0.24 (petroleum ether/ethyl acetate = 1/1); [α]25 = −63.7 (c = 1.0,
D
CHCl3); 1H NMR (400 MHz, CDCl3) δ 8.60 (d, J = 8.5 Hz, 1H), 8.09
(d, J = 8.8 Hz, 1H), 7.85 (d, J = 9.1 Hz, 1H), 7.75−7.63
(m, 1H), 7.38−7.27 (m, 2H), 7.09 (d, J = 8.9 Hz, 1H), 7.04−6.97
(m, 3H), 6.93−6.83 (m, 3H), 6.53 (d, J = 16.3 Hz, 1H), 3.93 (s, 3H),
3.66 (s, 3H), 3.62 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 163.4,
161.1, 157.4, 154.3, 147.0, 134.9, 134.6, 134.3, 133.5, 132.3, 129.2,
128.7, 128.2, 128.1, 124.3, 123.2, 122.9, 119.8, 115.4, 115.2, 113.1,
110.5, 60.2, 56.4, 56.0; 19F NMR (377 MHz, CDCl3) δ −114.44
(s, 1F); HRMS (ESI, m/z) calcd for C27H23FO4SNa [M + Na]+
485.1199, found 485.1204.
(R,E)-2-Methoxy-1-(2-styrylphenylsulfinyl)naphthalene (5e).
White solid: 0.98 g, 51% yield; mp 64−66 °C; Rf = 0.44 (petroleum
1
ether/ethyl acetate = 1/1); [α]25 = −136.4 (c = 0.6, CHCl3); H
D
NMR (400 MHz, CDCl3) δ 8.82 (d, J = 8.7 Hz, 1H), 8.38 (d, J =
8.0 Hz, 1H), 7.86 (d, J = 9.1 Hz, 1H), 7.74 (d, J = 8.2 Hz, 1H), 7.60−7.47
(m, 3H), 7.39 (dd, J = 14.9, 7.3 Hz, 2H), 7.23−7.15 (m, 3H), 7.09−
6.98 (m, 4H), 6.69 (d, J = 15.9 Hz, 1H), 3.72 (s, 3H); 13C NMR
(100 MHz, CDCl3) δ 157.6, 141.5, 136.7, 135.2, 134.9, 132.4, 131.5,
130.0, 129.3, 129.0, 128.6, 128.5, 128.0, 127.4, 126.8, 126.7, 125.8, 124.5,
124.0, 122.8, 113.4, 56.6; HRMS (ESI, m/z) calcd for C25H20O2SNa
[M + Na]+ 407.1082, found 407.1089.
(R,E)-1-(4,5-Dimethoxy-2-(4-methoxystyryl)phenylsulfinyl)-2-
methoxynaphthalene (5l). White solid: 1.18 g, 50% yield; mp
100−103 °C; Rf = 0.12 (petroleum ether/ethyl acetate = 1/1); [α]25
=
D
−165.3 (c = 0.9, CHCl3); 1H NMR (400 MHz, CDCl3) δ 8.90 (d, J =
8.7 Hz, 1H), 7.95−7.83 (m, 2H), 7.75 (d, J = 8.2 Hz, 1H), 7.62−7.52
(m, 1H), 7.40 (p, J = 7.2 Hz, 1H), 7.10 (d, J = 9.1 Hz, 1H), 7.02−6.94
(m, 3H), 6.94−6.85 (m, 1H), 6.73 (d, J = 8.7 Hz, 2H), 6.59 (d, J =
15.8 Hz, 1H), 4.05 (s, 3H), 3.92 (s, 3H), 3.81 (s, 3H), 3.78 (s, 3H);
13C NMR (100 MHz, CDCl3) δ 159.4, 157.4, 150.5, 148.8, 135.0,
(R,E)-2-Methoxy-1-(2-(4-methoxystyryl)phenylsulfinyl)-
naphthalene (5f). White solid: 1.24 g, 60% yield; mp 81−84 °C; Rf =
0.39 (petroleum ether/ethyl acetate = 1/1); [α]25D = −180.4 (c = 0.8,
1
CHCl3); H NMR (400 MHz, CDCl3) δ 8.83 (d, J = 8.6 Hz, 1H),
133.2, 132.4, 129.8, 129.3, 129.1, 129.0, 128.5, 128.1, 127.9, 124.5, 122.8,
121.5, 114.0, 113.4, 109.2, 107.8, 56.8, 56.5, 56.2, 55.4; HRMS (ESI, m/z)
calcd for C28H26O5SNa [M + Na]+ 497.1399, found 497.1398.
(R,E)-1-(2-(4-Fluorostyryl)-4,5-dimethoxyphenylsulfinyl)-2-methoxy-
naphthalene (5m). White solid: 1.57 g, 68% yield; mp 175−177 °C;
Rf = 0.14 (petroleum ether/ethyl acetate = 1/1); [α]25D = −151.7 (c =
1.0, CHCl3); 1H NMR (400 MHz, CDCl3) δ 8.88 (d, J = 8.6 Hz, 1H),
7.94−7.83 (m, 2H), 7.76 (d, J = 8.1 Hz, 1H), 7.55 (ddd, J = 8.4, 6.9,
1.2 Hz, 1H), 7.44−7.36 (m, 1H), 7.10 (d, J = 9.1 Hz, 1H), 6.99−6.84
(m, 6H), 6.58 (d, J = 15.9 Hz, 1H), 4.06 (s, 3H), 3.93 (s, 3H), 3.77 (s,
3H); 13C NMR (100 MHz, CDCl3) δ 163.6, 160.9, 157.4, 150.5,
149.1, 135.0, 133.6, 133.1, 132.4, 129.3, 129.0, 128.5, 128.3, 128.2,
128.1, 127.5, 124.5, 123.5, 122.6, 115.6, 115.4, 113.5, 109.2, 107.9,
56.7, 56.5, 56.2; 19F NMR (377 MHz, CDCl3) δ −114.45 (s, 1F);
HRMS (ESI, m/z) calcd for C27H23FO4SNa [M + Na]+ 485.1199,
found 485.1193.
8.41−8.31 (m, 1H), 7.86 (d, J = 9.1 Hz, 1H), 7.74 (d, J = 8.1 Hz, 1H),
7.59−7.45 (m, 3H), 7.38 (td, J = 7.3, 3.1 Hz, 2H), 7.08 (d, J = 9.1 Hz,
1H), 6.94 (d, J = 8.7 Hz, 2H), 6.87 (d, J = 15.9 Hz, 1H), 6.72 (d, J =
8.7 Hz, 2H), 6.65 (d, J = 15.9 Hz, 1H), 3.80 (s, 3H), 3.73 (s, 3H); 13C
NMR (100 MHz, CDCl3) δ 159.6, 157.6, 141.3, 135.1, 132.4, 130.9,
129.9, 129.6, 129.3, 129.0, 128.5, 128.1, 127.0, 126.6, 125.5, 124.4,
122.8, 121.7, 113.9, 113.5, 56.6, 55.4; HRMS (ESI, m/z) calcd for
C26H22O3SNa [M + Na]+ 437.1187, found 437.1190.
(R,E)-2-Methoxy-1-(4-methoxy-2-(4-methoxystyryl)-
phenylsulfinyl)naphthalene (5h). White solid: 1.15 g, 52% yield;
mp 116−119 °C; Rf = 0.25 (petroleum ether/ethyl acetate = 1/1);
[α]25D = −216.6 (c = 1.2, CHCl3); 1H NMR (400 MHz, CDCl3) δ 8.89
(d, J = 8.6 Hz, 1H), 8.23 (d, J = 8.5 Hz, 1H), 7.86 (d, J = 9.0 Hz, 1H),
7.75 (d, J = 8.2 Hz, 1H), 7.55 (t, J = 7.4 Hz, 1H), 7.38 (t, J = 7.5 Hz,
1H), 7.10 (d, J = 9.1 Hz, 1H), 7.02 (d, J = 8.9 Hz, 4H), 6.96 (d, J =
15.9 Hz, 1H), 6.75 (d, J = 8.7 Hz, 2H), 6.68 (d, J = 15.9 Hz, 1H), 3.86
(s, 3H), 3.81 (s, 3H), 3.78 (s, 3H); 13C NMR (100 MHz, CDCl3) δ
161.2, 159.7, 157.4, 136.8, 134.9, 132.5, 131.2, 130.0, 129.6, 129.4. 128.9,
128.5, 128.4, 128.2, 124.4, 122.9, 121.8, 114.0, 113.4, 112.9, 110.7, 110.1,
56.8, 55.8, 55.5; HRMS (ESI, m/z) calcd for C27H24O4SNa [M + Na]+
467.1293, found 467.1286.
(R,E)-1-(2-(4-Fluorostyryl)-4-methoxyphenylsulfinyl)-2-methoxy-
naphthalene (5i). White solid: 1.43 g, 66% yield; mp 152−155 °C;
Rf = 0.33 (petroleum ether/ethyl acetate = 1/1); [α]24D = −161.5 (c =
1.1, CHCl3); 1H NMR (400 MHz, CDCl3) δ 8.87 (d, J = 8.6 Hz, 1H),
8.24 (d, J = 8.8 Hz, 1H), 7.86 (d, J = 9.1 Hz, 1H), 7.74 (d, J = 8.1 Hz,
1H), 7.54 (t, J = 7.7 Hz, 1H), 7.43−7.33 (m, 1H), 7.13−6.94 (m, 6H),
6.89 (t, J = 8.6 Hz, 2H), 6.65 (d, J = 15.9 Hz, 1H), 3.85 (s, 3H), 3.76
(s, 3H); 13C NMR (100 MHz, CDCl3) δ 163.8, 161.4, 161.2, 157.4,
136.3, 134.9, 133.2, 132.9, 132.4, 130.4, 129.4, 129.0, 128.7, 128.6,
128.5, 128.4, 124.5, 123.8, 123.7, 122.8, 115.6, 115.4, 113.5, 113.2,
(R,E)-2-Methoxy-1-(4-(methoxymethoxy)-2-(4-methoxystyryl)-
phenylsulfinyl)naphthalene (5n). White solid: 1.16 g, 49% yield; mp
95−97 °C; Rf = 0.30 (petroleum ether/ethyl acetate = 1/1); [α]26
=
D
−300.7 (c = 1.7, CHCl3); 1H NMR (400 MHz, CDCl3) δ 8.88 (d, J =
8.7 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.83 (d, J = 9.1 Hz, 1H), 7.72
(d, J = 8.1 Hz, 1H), 7.54 (t, J = 7.8 Hz, 1H), 7.37 (t, J = 7.5 Hz, 1H),
7.17−7.11 (m, 2H), 7.07 (d, J = 9.1 Hz, 1H), 7.01 (d, J = 8.6 Hz, 2H),
6.94 (d, J = 15.8 Hz, 1H), 6.74 (d, J = 8.6 Hz, 2H), 6.68 (d, J =
15.8 Hz, 1H), 5.20 (s, 2H), 3.79 (s, 3H), 3.76 (s, 3H), 3.47 (s, 3H); 13C
NMR (100 MHz, CDCl3) δ 159.6, 158.9, 157.3, 136.7, 134.9, 134.0,
132.3, 131.2, 129.4, 129.3, 128.9, 128.4, 128.2, 124.4, 123.0, 122.8,
121.4, 115.0, 113.9, 113.3, 112.6, 94.5, 56.7, 56.3, 55.4; HRMS (ESI,
m/z) calcd for C28H26O5SNa [M + Na]+ 497.1399, found 497.1381.
(R,E)-2-Methoxy-1-(4-methoxy-2-(2,4,6-trimethoxystyryl)-
phenylsulfinyl)naphthalene (5o). White solid: 1.08 g, 43% yield; mp
68−70 °C; Rf = 0.22 (petroleum ether/ethyl acetate = 1/1); [α]26D = −150.9
3076
dx.doi.org/10.1021/jo3003562 | J. Org. Chem. 2012, 77, 3071−3081