M. Xie et al. / Journal of Organometallic Chemistry 695 (2010) 882–886
885
1.05 (t, J = 7.5 Hz, 3H), 0.82 (t, J = 7.0 Hz, 3H); 13C NMR (75 MHz,
CDCl3): d 160.6, 158.9, 143.6, 140.6, 138.3, 134.2, 129.5, 127.0,
126.9, 113.7, 71.1, 55.3, 33.6, 29.9, 27.3, 23.2, 21.5, 13.8, 13.1; Anal.
Calc. for C23H30O4S: C, 68.62; H, 7.51; found: C, 68.65; H, 7.33; IR
(KBr) v (cmꢀ1) 3504, 2933, 1608, 1510, 1379, 1247, 1136.
C23H21BrO3S: C, 60.40; H, 4.63; found: C, 60.62; H, 4.77; IR (KBr)
v (cmꢀ1) 3481, 2918, 1595, 1485, 1340, 1284, 1132.
3.2.14. (Z)-1-(4-Chlorophenyl)-3-phenyl-2-tosylbut-2-en-1-ol (4n)
White solid; m.p. 130–132 °C; 1H NMR (300 MHz, CDCl3) d 7.54
(d, J = 8.4 Hz, 2H), 7.41 (d, J = 8.3 Hz, 2H), 7.28–7.13 (m, 4H), 7.04–
6.96 (m, 3H), 6.90–6.78 (br, 2H), 6.14 (d, J = 10.1 Hz, 1H), 4.46 (d,
J = 10.7 Hz, 1H), 2.35 (s, 3H), 2.19 (s, 3H); 13C NMR (75 MHz, CDCl3)
d 153.3, 143.4, 141.7, 140.2, 139.7, 138.5, 133.3, 128.9, 128.7,
127.8, 127.7, 127.4, 126.9, 71.1, 25.6, 21.5; Anal. Calc. for
C23H21ClO3S: C, 66.90; H, 5.13; found: C, 66.50; H, 5.22; IR (KBr)
v (cmꢀ1) 3529, 2954, 1595, 1489, 1340, 1294, 1083.
3.2.8. (Z)-1-(4-Bromophenyl)-3-ethyl-2-tosylhept-2-en-1-ol (4h)
White solid; m.p. 96–98 °C; 1H NMR (300 MHz, CDCl3) d 7.67 (d,
J = 8.2 Hz, 2H), 7.49–7.45 (m, 2H), 7.34–7.22 (m, 4H), 5.86 (d,
J = 10.8 Hz, 1H), 4.30 (d, J = 11.0 Hz, 1H), 2.45–2.43 (m, 5H), 2.28
(q, J = 7.6 Hz, 2H), 1.27–1.23 (m, 4H), 1.06 (t, J = 7.5 Hz, 3H), 0.83
(t, J = 7.0 Hz, 3H); 13C NMR (75 MHz, CDCl3) d 161.5, 143.9, 141.2,
140.3, 137.9, 131.4, 129.5, 127.5, 127.0, 121.3, 70.9, 33.7, 30.0,
27.5, 23.2, 21.5, 13.8, 13.1; Anal. Calc. for C22H27BrO3S: C, 58.53;
H, 6.03; found: C, 58.68; H, 6.16; IR (KBr) v (cmꢀ1) 3471, 2962,
1606, 1467, 1377, 1280, 1130.
3.2.15. (Z)-3-Methyl-1-phenyl-2-tosylhept-2-en-1-ol (4o)
Colorless oil; 1H NMR (300 MHz, CDCl3) d 7.65 (d, J = 8.1 Hz, 2H),
7.45–7.24 (m, 7H), 5.98 (d, J = 10.7 Hz, 1H), 4.32 (d, J = 10.8 Hz, 1H),
2.48 (q, J = 4.6 Hz, 2H), 2.42 (s, 3H), 1.96 (s, 3H), 1.32–1.21 (m, 4H),
0.84 (t, J = 6.8 Hz, 3H); 13C NMR (75 MHz, CDCl3) d 156.1, 143.8,
141.8, 140.2, 138.7, 129.5, 128.4, 127.3, 127.2, 125.6, 71.6, 36.3,
29.7, 23.1, 21.6, 21.5, 13.9; Anal. Calc. for C21H26O3S: C, 70.36; H,
7.31; found: C, 70.65; H, 7.65; IR (KBr) v (cmꢀ1) 3568, 2953,
1560, 1490, 1344, 1276, 1122.
3.2.9. (Z)-1-(4-Chlorophenyl)-3-ethyl-2-tosylhept-2-en-1-ol (4i)
White solid; m.p. 73–76 °C; 1H NMR (300 MHz, CDCl3) d 7.68 (d,
J = 7.8 Hz, 2H), 7.40–7.27 (m, 6H), 5.88 (d, J = 10.7 Hz, 1H), 4.31 (d,
J = 10.9 Hz, 1H), 2.59–2.41 (m, 5H), 2.29–2.25 (m, 2H), 1.36–1.18
(m, 4H), 1.05 (t, J = 7.3 Hz, 3H), 0.83 (t, J = 6.8 Hz, 3H); 13C NMR
(75 MHz, CDCl3) d 161.5, 143.9, 140.7, 140.4, 138.0, 133.1, 129.5,
128.5, 127.2, 127.0, 70.9, 33.7, 30.0, 27.4, 23.2, 21.5, 13.8, 13.1;
Anal. Calc. for C22H27ClO3S: C, 64.93; H, 6.69; found: C, 65.20; H,
6.86; IR (KBr) v (cmꢀ1) 3469, 2962, 1606, 1490, 1350, 1280, 1130.
3.2.16. (Z)-1-(4-Methoxyphenyl)-3-methyl-2-tosylhept-2-en-1-ol
(4p)
Yellow oil; 1H NMR (300 MHz, CDCl3) d 7.70 (d, J = 7.9 Hz, 2H),
7.36 (d, J = 8.2 Hz, 2H), 7.25 (d, J = 7.9 Hz, 2H), 6.90 (d, J = 8.3 Hz,
2H), 5.92 (d, J = 10.7 Hz, 1H), 4.29 (d, J = 10.7 Hz, 1H), 3.83 (s,
3H), 2.49–2.42 (m, 5H), 1.94 (s, 3H), 1.27–1.20 (m, 3H), 1.10–1.08
(m, 1H), 0.83 (t, J = 6.8 Hz, 3H); 13C NMR (75 MHz, CDCl3) d
158.9, 155.7, 143.7, 140.4, 138.6, 133.8, 129.5, 127.1, 126.9,
113.8, 71.4, 55.3, 36.2, 29.7, 23.0, 21.5, 21.4, 13.9; Anal. Calc. for
C22H28O4S: C, 68.01; H, 7.26; found: C, 68.35; H, 7.41; IR (KBr) v
(cmꢀ1) 3498, 2937, 1583, 1510, 1354, 1199, 1085.
3.2.10. (Z)-1,3-Diphenyl-2-tosylbut-2-en-1-ol (4j)
White solid; m.p. 139–141 °C; 1H NMR (300 MHz, CDCl3) d 7.60
(d, J = 7.3 Hz, 2H), 7.48–7.43 (m, 2H), 7.38–7.36 (m, 1H), 7.21–7.16
(m, 5H), 6.98–6.92 (m, 4H), 6.20 (d, J = 10.0 Hz, 1H), 4.46 (d,
J = 10.5 Hz, 1H), 2.34 (s, 3H), 2.20 (s, 3H); 13C NMR (75 MHz,
CDCl3): d 153.2, 143.3, 142.1, 141.8, 139.9, 138.7, 128.9, 128.6,
127.8, 127.7, 127.6, 127.5, 127.4, 125.5, 71.3, 25.7, 21.5; Anal. Calc.
for C23H22O3S: C, 72.99; H, 5.86; found: C, 72.68; H, 5.75; IR (KBr) v
(cmꢀ1) 3477, 2916, 1597, 1492, 1355, 1278, 1134.
3.2.17. (Z)-1-(2,4-Dimethoxyphenyl)-3-methyl-2-tosylhept-2-en-1-ol
(4q)
3.2.11. (Z)-1-(4-Methoxyphenyl)-3-phenyl-2-tosylbut-2-en-1-ol (4k)
White solid; m.p. 166–169 °C; 1H NMR (300 MHz, CDCl3) d 7.50
(d, J = 8.5 Hz, 2H), 7.25–7.10 (m, 4H), 7.02–6.87 (m, 7H), 6.12 (d,
J = 10.7 Hz, 1H), 4.43 (d, J = 10.8 Hz, 1H), 3.84 (s, 3H), 2.32 (s, 3H),
2.16 (s, 3H); 13C NMR (75 MHz, CDCl3) d 158.9, 152.5, 143.2,
141.9, 139.9, 138.8, 133.6, 128.8, 127.7, 127.6, 127.4, 126.7,
113.9, 71.4, 55.3, 25.5, 21.5; Anal. Calc. for C24H24O4S: C, 70.56;
H, 5.92; found: C, 70.28; H, 5.77; IR (KBr) v (cmꢀ1) 3469, 2954,
1597, 1458, 1361, 1249, 1136.
White solid; m.p. 82–85 °C; 1H NMR (300 MHz, CDCl3) d 7.49–
7.43 (m, 3H), 7.14 (d, J = 7.2 Hz, 2H), 6.54 (d, J = 8.3 Hz, 1H), 6.25
(s, 1H), 6.01 (d, J = 9.7 Hz, 1H), 4.31 (d, J = 9.7 Hz, 1H), 3.82 (s,
3H), 3.63 (s, 3H), 2.76–2.57 (m, 1H), 2.47–2.40 (m, 1H), 2.38 (s,
3H), 2.02 (s, 3H), 1.38–1.19 (m, 4H), 0.87 (t, J = 7.0 Hz, 3H); 13C
NMR (75 MHz, CDCl3) d 160.5, 157.4, 156.8, 143.1, 140.1, 136.6,
129.1, 128.5, 126.6, 121.6, 103.9, 97.9, 68.1, 55.4, 54.9, 36.4, 30.3,
23.0, 22.1, 21.4, 13.9; Anal. Calc. for C23H30O5S: C, 66.00; H, 7.22;
found: C, 66.29; H, 7.09; IR (KBr) v (cmꢀ1) 3535, 2951, 1558,
1490, 1298, 1207, 1136.
3.2.12. (Z)-1-(2,4-Dimethoxyphenyl)-3-phenyl-2-tosylbut-2-en-1-ol
(4l)
3.2.18. (Z)-1-(4-Bromophenyl)-3-methyl-2-tosylhept-2-en-1-ol (4r)
White solid; m.p. 119–122 °C; 1H NMR (300 MHz, CDCl3) d 7.67
(d, J = 6.8 Hz, 2H), 7.48–7.46 (m, 2H), 7.30–7.26 (m, 4H), 5.89 (d,
J = 10.5 Hz, 1H), 4.25 (d, J = 9.3 Hz, 1H), 2.53–2.49 (m, 2H), 2.44
(s, 3H), 1.95 (s, 3H), 1.28–1.22 (m, 3H), 1.13–1.10 (m, 1H), 0.84
(t, J = 6.9 Hz, 3H); 13C NMR (75 MHz, CDCl3) d 156.6, 143.9, 140.9,
140.0, 138.2, 131.5, 129.6, 127.4, 127.0, 121.3, 71.1, 36.3, 29.8,
23.0, 21.6, 21.5, 13.9; Anal. Calc. for C21H25BrO3S: C, 57.67; H,
5.76; found: C, 57.87; H, 5.83; IR (KBr) v (cmꢀ1) 3486, 2960,
1610, 1485, 1392, 1269, 1138.
White solid; m.p. 133–136 °C; 1H NMR (300 MHz, CDCl3) d 7.63
(d, J = 8.5 Hz, 1H), 7.22–7.13 (m, 3H), 6.98–6.92 (m, 4H), 6.86 (d,
J = 7.2 Hz, 2H), 6.64–6.61 (m, 1H), 6.43 (s, 1H), 6.23 (d,
J = 10.0 Hz, 1H), 4.59 (d, J = 10.1 Hz, 1H), 3.86 (s, 3H), 3.77 (s, 3H),
2.33 (s, 3H), 2.25 (s, 3H); 13C NMR (75 MHz, CDCl3) d 160.6,
157.4, 152.8, 142.9, 140.9, 140.1, 139.2, 128.6, 128.2, 127.6,
127.4, 127.3, 121.4, 104.1, 98.2, 68.2, 55.4, 55.2, 25.9, 21.5; Anal.
Calc. for C25H26O5S: C, 68.47; H, 5.98; found: C, 68.37; H, 5.88; IR
(KBr) v (cmꢀ1) 3489, 2956, 1587, 1496, 1417, 1139, 1083.
3.2.13. (Z)-1-(4-Bromophenyl)-3-phenyl-2-tosylbut-2-en-1-ol (4m)
White solid; m.p. 121–124 °C; 1H NMR (300 MHz, CDCl3) d
7.56–7.53 (m, 2H), 7.47–7.44 (m, 2H), 7.25–7.11 (m, 3H), 7.01–
6.94 (m, 4H), 6.90–6.82 (br, 2H), 6.09 (d, J = 10.5 Hz, 1H), 4.42 (d,
J = 10.5 Hz, 1H), 2.32 (s, 3H), 2.17 (s, 3H); 13C NMR (75 MHz,
CDCl3): d 153.6, 143.5, 141.7, 140.9, 139.7, 138.4, 131.6, 128.9,
127.8, 127.6, 127.5, 127.4, 121.3, 70.8, 25.6, 21.6; Anal. Calc. for
3.2.19. (Z)-1-(4-Chlorophenyl)-3-methyl-2-tosylhept-2-en-1-ol (4s)
White solid; m.p. 109–111 °C; 1H NMR (300 MHz, CDCl3) d 7.68
(d, J = 7.7 Hz, 2H), 7.38–7.28 (m, 6H), 5.91 (d, J = 10.7 Hz, 1H), 4.26
(d, J = 10.8 Hz, 1H), 2.51–2.46 (m, 2H), 2.43 (s, 3H), 1.95 (s, 3H),
1.33–1.21 (m, 3H), 1.12–1.09 (m, 1H), 0.84 (t, J = 6.8 Hz, 3H); 13C
NMR (75 MHz, CDCl3): d 156.5, 143.9, 140.4, 140.1, 138.3, 133.1,
129.6, 128.5, 127.1, 127.0, 71.1, 36.3, 29.8, 23.0, 21.6, 13.9; Anal.