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Yanli Xu et al.
148, 117, 89; ESI-HR-MS: m/z=389.9399, calcd. for
C14H10BrNNaO4S [M+Na]+: 389.9406.
(EI): m/z=245, 216, 180, 125, 104, 92; ESI-HR-MS: m/z=
268.0411, calcd. for C13H11NNaO2S [M+Na]+: 268.0403.
(E)-Methyl 3-(phenylsulfonyl)acrylate (3bn):[27] Colorless
oil; 1H NMR (400 MHz, CDCl3): d=7.92 (d, J=7.7 Hz,
2H), 7.69 (t, J=7.4 Hz, 1H), 7.59 (t, J=7.7 Hz, 2H), 7.34
(d, J=15.2 Hz, 1H), 6.84 (d, J=15.2 Hz, 1H), 3.80 (s, 3H);
13C NMR (100 MHz, CDCl3): d=163. 9, 143. 5, 138.5, 134.4,
130.5, 129.6, 128.3, 52.8; IR (KBr): n=2924, 1729, 1584,
1441, 1303, 1274, 1232, 817, 754, 571 cmÀ1; MS (EI): m/z=
226, 195, 161, 125, 97, 77.
(E)-1-Nitro-4-(2-{[4-(trifluoromethyl)phenyl]sulfonyl}vi-
nyl)benzene (3jl): Yellow solid; mp 169–1718C; 1H NMR
(400 MHz, DMSO-d6): d=8.27 (d, J=8.8 Hz, 2H), 8.18 (d,
J=8.4 Hz, 2H), 8.07 (d, J=8.4 Hz, 2H), 8.04 (d, J=8.8 Hz,
2H), 7.95 (d, J=15.5 Hz, 1H), 7.88 (d, J=15.5 Hz, 1H);
13C NMR (100 MHz, DMSO-d6): d=148.6, 143.9, 140.9,
138.5, 131.2, 130.3, 128.5, 126.9, 126.9, 124.0; IR (KBr): n=
3052, 2923, 2853, 1647, 1529, 1320, 1137, 836, 746 cmÀ1; MS
(EI): m/z=357, 327, 193, 165, 118, 102; ESI-HR-MS: m/z=
380.0176, calcd. for C15H10F3NNaO4S [M+Na]+: 380.0175.
(E)-1-[(4-Nitrostyryl)sulfonyl]-2-(trifluoromethoxy)ben-
zene (3kl): Yellow solid; mp 158–1598C; 1H NMR
(400 MHz, CDCl3): d=8.25 (d, J=8.3 Hz, 2H), 8.15 (d, J=
7.6 Hz, 1H), 7.80 (d, J=15.4 Hz, 1H), 7.72 (d, J=8.1 Hz,
1H), 7.68 (d, J=8.3 Hz, 2H), 7.49 (t, J=7.6 Hz, 1H), 7.41
(d, J=8.1 Hz, 1H), 7.11 (d, J=15.4 Hz, 1H); 13C NMR
(100 MHz, CDCl3): d=149.1, 146.7, 142.1, 138.2, 135.8,
131.8, 130.5, 130.2, 129.3, 126.9, 124.3 120.0; IR (KBr): n=
3063, 2925, 1596, 1522 1344, 1248, 1151, 1068, 841, 746,
695 cmÀ1; MS (EI): m/z=373, 309, 262, 209, 115, 89; ESI-
HR-MS: m/z=396.0124, calcd. for C15H10F3NNaO5S [M+
Na]+: 396.0124.
(E)-Ethyl 3-(phenylsulfonyl)acrylate (3bp):[27] Colorless
oil; 1H NMR (400 MHz, CDCl3): d=7.92 (d, J=7.8 Hz,
2H), 7.69 (t, J=7.4 Hz, 1H), 7.59 (t, J=7.4 Hz, 2H), 7.33
(d, J=15.2 Hz, 1H), 6.83 (d, J=15.2 Hz, 1H), 4.25 (q, J=
7.2 Hz, 2H), 1.29 (d, J=7.2 Hz, 3H); 13C NMR (100 MHz,
CDCl3): d=163.4, 143.2, 138.5, 134.4, 131.0, 129.6, 128.3,
62.0, 14.0; IR (KBr): n=2984, 1724, 1583, 1447, 1384, 1298,
1231, 736, 689, 571 cmÀ1; MS (EI): m/z=240, 195, 167, 125,
97, 77.
(Vinylsulfonyl)benzene (3br):[11] Colorless oil; 1H NMR
(400 MHz, CDCl3): d=7.90 (d, J=7.8 Hz, 2H), 7.64 (t, J=
7.4 Hz, 1H), 7.55 (t, J=7.6 Hz, 2H), 6.66 (dd, J=16.5,
9.8 Hz, 1H), 6.46 (d, J=16.5 Hz, 1H), 6.04 (d, J=9.8 Hz,
1H); 13C NMR (100 MHz, CDCl3): d=139.6, 138.5, 133.6,
129.3, 127.9, 127.7; IR (KBr): n=3061, 2923, 1635, 1448,
1383, 1310, 1143, 976, 744, 694, 558 cmÀ1; MS (EI): m/z=
168, 141, 125, 97, 77, 65.
(E)-2-[(4-Nitrostyryl)sulfonyl]thiophene (3gl): Yellow
1
solid; mp 143–1458C; H NMR (400 MHz, CDCl3): d=8.25
(d, J=8.4 Hz, 2H), 7.76 (d, J=3.6 Hz, 2H), 7.71 (d, J=
15.5 Hz, 1H), 7.66 (d, J=8.4 Hz, 2H), 7.18 (t, J=4.2 Hz,
1H), 7.11 (d, J=15.5 Hz, 1H); 13C NMR (100 MHz, CDCl3):
d=149.1, 141.1, 138.9, 138.3, 134.8, 134.2, 132.2, 129.3, 128.3,
124.3; IR (KBr): n=3063, 2925, 1655, 1518, 1342, 1307,
1243, 1139, 1060, 812, 747 cmÀ1; MS (EI): m/z=295, 231,
184, 152, 131, 102; ESI-HR-MS: m/z=317.9872, calcd. for
C12H9NNaO4S2 [M+Na]+: 317.9865.
(E)-[2-(Phenylsulfonyl)vinyl]benzene (3bs):[28] Pale yellow
1
solid; mp 67–698C; H NMR (400 MHz, CDCl3): d=7.96 (d,
J=7.7 Hz, 2H), 7.69 (d, J=15.4 Hz, 1H), 7.62 (t, J=7.2 Hz,
1H), 7.55 (t, J=7.7 Hz, 2H), 7.48 (d, J=6.8 Hz, 2H), 7.39
(d, J=6.2 Hz, 3H), 6.87 (d, J=15.4 Hz, 1H); 13C NMR
(100 MHz, CDCl3): d=142.5, 140.7, 133.3, 132.3, 131.2,
129.3, 129.0, 128.5, 127.6, 127.3; IR (KBr): n=3059, 2924,
(E)-1-[2-(Ethylsulfonyl)vinyl]-4-nitrobenzene
(3ll):
1615, 1492, 1447, 1309, 1146, 1084, 975, 817, 749, 689 cmÀ1
;
1
Yellow solid; mp 161–1628C; H NMR (400 MHz, CDCl3):
d=8.27 (d, J=8.5 Hz, 2H), 7.69 (d, J=8.5 Hz, 2H), 7.66 (d,
J=15.5 Hz, 1H), 6.99 (d, J=15.5 Hz, 1H), 3.13 (q, J=
7.4 Hz, 2H), 1.40 (t, J=7.4 Hz, 3H); 13C NMR (100 MHz,
CDCl3): d=149.1, 142.1, 138.2, 129.3, 128.5, 124.3, 49.3, 7.1;
IR (KBr): n=3060, 2927, 2363, 1596, 1520, 1345, 1308, 1271,
843, 749 cmÀ1; MS (EI): m/z=241, 212, 164, 148, 118, 102;
ESI-HR-MS: m/z=264.0297, calcd. for C10H11NNaO4S [M+
Na]+: 264.0301.
MS (EI): m/z=244, 179, 125, 102, 92, 77.
(E)-1-Methyl-4-(styrylsulfonyl)benzene
(3as):[28]
Pale
1
yellow solid; mp 100–1028C; H NMR (400 MHz, CDCl3):
d=7.83 (d, J=7.8 Hz, 2H), 7.65 (d, J=15.4 Hz, 1H), 7.47
(d, J=7.8 Hz, 2H), 7.41–7.32 (m, 5H), 6.85 (d, J=15.4 Hz,
1H), 2.43 (s, 3H); 13C NMR (100 MHz, CDCl3): d=144.4,
141.9, 137.8, 132.5, 131.1, 129.9, 129.0, 128.5, 127.7, 127.6,
21.6; IR (KBr): n=3056, 2920, 1659, 1549, 1299, 1120, 973,
815, 748, 685 cmÀ1; MS (EI): m/z=258, 193, 179, 139, 119,
102.
(E)-1-[2-(Cyclopropylsulfonyl)vinyl]-4-nitrobenzene
(3ml): Yellow solid; mp 157–1588C; 1H NMR (400 MHz,
CDCl3): d=8.28 (d, J=8.6 Hz, 2H), 7.69 (d, J=8.6 Hz, 2H),
7.61 (d, J=15.5 Hz, 1H), 7.05 (d, J=15.5 Hz, 1H), 2.56–2.40
(m, 1H), 1.38–1.29 (m, 2H), 1.15–1.06 (m, 2H); 13C NMR
(100 MHz, CDCl3): d=149.0, 140.1, 138.5, 123.0, 129.2,
124.3, 31.1, 5.5; IR (KBr): n=3048, 2924, 1597, 1519, 1345,
1295, 1131, 843, 745 cmÀ1; MS (EI): m/z=253, 204, 148, 118,
102, 89; ESI-HR-MS: m/z=276.0295, calcd. for
C11H11NNaO4S [M+Na]+: 276.0301.
(E)-1-Methoxy-4-(styrylsulfonyl)benzene (3fs):[28] Pale
1
yellow solid; mp 110–1128C; H NMR (400 MHz, CDCl3):
d=7.87 (d, J=8.7 Hz, 2H), 7.63 (d, J=15.5 Hz, 1H), 7.48–
7.46 (m, 2H), 7.43–7.33 (m, 3H), 7.00 (d, J=8.7 Hz, 2H),
6.84 (d, J=15.5 Hz, 1H), 3.86 (s, 3H); 13C NMR (100 MHz,
CDCl3): d=163.6, 141.4, 132.5, 132.2, 131.0, 129.9, 129.0,
128.5, 127.9, 114.6, 55.7; IR (KBr): n=3058, 2923, 1586,
1496, 1454, 1259, 1139, 1085, 817, 749 cmÀ1; MS (EI): m/z=
274, 210, 194, 155, 123, 77.
(E)-2-[2-(Phenylsulfonyl)vinyl]pyridine (3bm): Yellow oil;
1H NMR (400 MHz, CDCl3): d=8.56 (d, J=4.7 Hz, 1H),
7.92 (d, J=15.2 Hz, 1H), 7.91–7.89 (m, 1H), 7.69 (d, J=
7.7 Hz, 1H), 7.63–7.55 (m, 2H), 7.53–7.47 (m, 2H), 7.43 (d,
J=15.2 Hz, 1H), 7.40–7.35 (m, 1H), 7.25–7.20 (m, 1H);
13C NMR (100 MHz, CDCl3): d=150.9, 150.2, 140.5, 137.0,
133.5, 131.8, 129.3, 127.8, 127.3, 125.4, 125.0; IR (KBr): n=
3054, 2920, 1647, 1549, 1463, 1305, 1144, 819, 754 cmÀ1; MS
(E)-1-Fluoro-4-(styrylsulfonyl)benzene
(3cs):[28]
Pale
1
yellow solid; mp 95–968C; H NMR (400 MHz, CDCl3): d=
7.97 (d, J=8.1 Hz, 2H), 7.68 (d, J=15.4 Hz, 1H), 7.49 (d,
J=8.1 Hz, 2H), 7.43–7.38 (m, 3H), 7.24–7.20 (m, 2H), 6.84
(d, J=15.4 Hz, 1H); 13C NMR (100 MHz, CDCl3): d=166.9,
164.4, 142.7, 132.2, 131.3, 130.5, 129.11, 128.7, 127.1, 116.7,
116.5; IR (KBr): n=3058, 2919, 1654, 1563, 1410, 1272,
8
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Adv. Synth. Catal. 0000, 000, 0 – 0
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