Helvetica Chimica Acta – Vol. 94 (2011)
879
Ethyl (2Z)-3-(4-Chlorophenyl)-2-{[(4-methylphenyl)sulfonyl]methyl}prop-2-enoate (Table, Entry
4): Colorless oil. IR: 2985, 1715, 1315, 1268, 1131. 1H-NMR: 7.85 (s, 1 H); 7.70 (d, J ¼ 8.3, 2 H); 7.44 (d,
J ¼ 9.0, 2 H); 7.24 – 7.33 (m, 4 H); 4.44 (s, 2 H), 4.06 (q, J ¼ 6.7, 2 H); 2.40 (s, 3 H); 1.22 (t, J ¼ 6.7, 3 H).
13C-NMR: 166.1; 144.9; 136.2; 132.1; 130.5; 129.6; 128.9; 128.4; 121.7; 61.6; 54.9; 21.5; 14.0. ESI-MS: 379
([M þ H]þ).
(2E)-2-{[(4-Methylphenyl)sulfonyl]methyl}-3-phenyl-prop-2-enenitrile (Table, Entry 5): Light
1
brown solid. M.p. 908. IR: 2212, 1623, 1311, 1146. H-NMR: 7.81 (d, J ¼ 8.3, 2 H); 7.55 (s, 1 H); 7.34 –
7.40 (m, 7 H); 4.17 (s, 2 H); 2.46 (s, 3 H). 13C-NMR: 152.0; 132.2; 130.5; 130.1; 129.0; 128.9; 128.7;
118.1; 103.2; 56.4; 21.7. ESI-MS: 320 ([M þ Na]þ).
Methyl (2Z)-2-{[(4-Methylphenyl)sulfonyl]methyl}-3-(3-nitrophenyl)prop-2-enoate (Table, Entry 6):
Light yellow solid. M.p. 1108. IR: 2982, 1713, 1317, 1266, 1141. 1H-NMR: 8.20 (d, J ¼ 8.3, 2 H); 7.94 (d, J ¼
7.8, 1 H); 7.91 (s, 1 H); 7.71 (d, J ¼ 7.8, 2 H); 7.60 (t, J ¼ 7.8, 1 H); 7.28 (d, J ¼ 7.8, 2 H); 4.33 (s, 2 H); 3.69 (s,
3 H); 2.43 (s, 3 H). 13C-NMR: 166.5; 145.3; 140.3; 138.4; 135.6; 133.7; 129.5; 128.3; 127.4; 123.2; 56.5;
52.2; 21.2. ESI-MS: 376 ([M þ H]þ).
(2E)-3-(4-Ethoxyphenyl)-2-{[(4-methylphenyl)sulfonyl]methyl}prop-2-enenitrile (Table, Entry 7):
Yellow oil. IR: 2927, 2210, 1627, 1321, 1148. 1H-NMR: 7.54 (d, J ¼ 8.6, 2 H); 7.40 (d, J ¼ 6.7, 2 H); 7.26 (t,
J ¼ 6.7, 2 H); 6.81 (d, J ¼ 8.6, 2 H); 6.54 (s, 1 H), 4.01 (q, J ¼ 6.7, 2 H); 3.69 (s, 2 H); 2.43 (s, 3 H); 1.41 (t,
J ¼ 6.7, 3 H). 13C-NMR: 160.4; 144.0; 138.4; 133.2; 130.5; 129.3; 128.5; 127.4; 114.2; 104.2; 63.7; 57.2; 21.3;
14.6. ESI-MS: 364 ([M þ Na]þ).
(2E)-3-(4-Chlorophenyl)-2-{[(4-methylphenyl)sulfonyl]methyl}prop-2-enenitrile (Table, Entry 8):
1
White solid. M.p. 1108. IR: 2928, 2212, 1627, 1313, 1144. H-NMR: 7.80 (d, J ¼ 8.1, 1 H); 7.38 (m, 6 H);
7.30 (d, J ¼ 8.3, 2 H); 4.42 (s, 2 H); 2.47 (s, 3 H). 13C-NMR: 150.8; 145.2; 136.2; 134.9; 131.4; 130.7; 130.1;
129.3; 129.1; 128.6; 118.0; 103.4; 56.3; 21.7. ESI-MS: 354 ([M þ Na]þ).
(2E)-3-(Furan-2-yl)-2-{[(4-methylphenyl)sulfonyl]methyl}prop-2-enenitrile (Table, Entry 9): Brown
solid. M.p. 1258. IR: 2925, 2212, 1623, 1311, 1146. 1H-NMR: 7.78 (d, J ¼ 8.1, 2 H); 7.57 (s, 1 H); 7.38 (d, J ¼
8.1, 2 H); 7.04 (d, J ¼ 3.5, 1 H); 6.96 (s, 1 H); 6.54 (s, 1 H); 3.98 (s, 2 H), 2.45 (s, 3 H). 13C-NMR: 148.7;
145.8; 137.1; 134.5; 130.0; 128.5; 119.6; 117.1; 112.7; 112.2; 60.5; 21.6. ESI-MS: 305 ([M þ NH4]þ).
Methyl (2Z)-2-[(Phenylsulfonyl)methyl]-3-(thiophen-2-yl)prop-2-enoate (Table, Entry 10): Light
brown oil. IR: 2984, 1710, 1600, 1508, 1317, 1142. 1H-NMR: 8.00 (s, 1 H); 7.78 (d, J ¼ 8.3, 2 H); 7.57 (d, J ¼
3.7, 1 H); 7.52 (d, J ¼ 5.2, 1 H); 7.30 (d, J ¼ 8.3, 3 H); 7.12 (t, J ¼ 3.7, 1 H); 4.55 (s, 2 H); 3.54 (s, 3 H).
13C-NMR: 166.4; 139.0; 137.5; 134.2; 133.5; 131.5; 129.3; 128.5; 128.2; 62.4; 52.7. ESI-MS: 345 ([M þ
Na]þ).
Methyl (2Z)-2-{[(4-Methylphenyl)sulfonyl]methyl}-3-(thiophen-2-yl)prop-2-enoate (Table, Entry
11): Light brown oil. IR: 2984, 1710, 1600, 1508, 1317, 1142. 1H-NMR: 8.00 (s, 1 H); 7.78 (d, J ¼ 8.3,
2 H); 7.57 (d, J ¼ 3.7, 1 H); 7.52 (d, J ¼ 5.2, 1 H); 7.30 (d, J ¼ 8.3, 2 H); 7.12 (t, J ¼ 3.7, 1 H); 4.55 (s, 2 H);
3.54 (s, 3 H); 2.45 (s, 3 H). 13C-NMR: 166.4; 139.0; 137.5; 134.2; 133.5; 131.5; 129.3; 128.5; 128.2; 62.4;
52.7; 21.4. ESI-MS: 359 ([M þ Na]þ).
Methyl (2Z)-2-{[(4-Methylphenyl)sulfonyl]methyl}oct-2-enoate (Table, Entry 12): Colorless oil. IR:
2953, 1720, 1321, 1143, 1085. 1H-NMR: 7.72 (d, J ¼ 8.3, 2 H); 7.32 (d, J ¼ 8.3, 2 H); 7.09 (t, J ¼ 7.5, 1 H);
4.22 (s, 2 H); 3.05 (s, 3 H); 2.42 (s, 3 H); 2.14 (q, J ¼ 6.7, 2 H); 2.0 (m, 2 H); 1.32 (m, 4 H); 0.87 (t, J ¼ 7.5,
3 H). 13C-NMR: 165.7; 151.3; 144.3; 131.5; 129.2; 128.2; 120.2; 60.2; 53.6; 29.9; 28.7; 22.7; 21.9; 21.1; 13.7.
ESI-MS: 347 ([M þ Na]þ).
Methyl (2Z)-2-{[(4-Methylphenyl)sulfonyl]methyl}hept-2-enoate (Table, Entry 13): Colorless oil. IR:
2956, 1720, 1318, 1144, 1084. 1H-NMR: 7.72 (d, J ¼ 8.3, 2 H); 7.32 (d, J ¼ 8.3, 2 H); 7.09 (t, J ¼ 7.5, 1 H);
4.22 (s, 2 H); 3.05 (s, 3 H); 2.42 (s, 3 H); 2.14 (q, J ¼ 6.7, 2 H); 1.32 (m, 4 H); 0.87 (t, J ¼ 7.5, 3 H).
13C-NMR: 165.7; 151.3; 144.5; 131.5; 129.2; 128.2; 120.2; 60.2; 53.6; 29.9; 28.7; 21.9; 21.1; 13.7. ESI-MS:
333 ([M þ Na]þ).
Ethyl (2Z)-2-{[(4-Methylphenyl)sulfonyl]methyl}hex-2-enoate (Table, Entry 14): Colorless oil. IR:
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2948, 1720, 1319, 1146, 1087. H-NMR: 7.68 (d, J ¼ 6.9, 2 H); 7.28 (d, J ¼ 6.9, 2 H); 7.03 (t, J ¼ 7.5, 1 H);
4.15 (s, 2 H); 3.91 (q, J ¼ 7.1, 2 H); 2.42 (s, 3 H); 2.20 (q, J ¼ 7.5, 2 H); 1.46 (m, 2 H); 1.13 (t, J ¼ 7.1, 3 H ) ;
0.94 (t, J ¼ 7.1, 3 H ) . 13C-NMR: 165.0; 150.4; 136.4; 129.3; 128.8; 128.7; 60.6; 53.9; 31.8; 31.3; 21.5; 14.0;
13.8. ESI-MS: 333 ([M þ Na]þ).