Kondoh et al.
29.56, 29.61, 29.62, 30.2, 31.9, 36.1, 52.0, 124.1, 127.6, 128.3,
129.5, 131.2, 141.5, 166.9. Found: C, 72.82; H, 9.64. Calcd for
C22H34O2S: C, 72.88; H, 9.45. Mp: 36.0-37.5 °C (amorphous
solid).
3H), 4.17 (s, 0.17 × 2H), 4.20 (s, 0.83 × 2H), 6.49 (s, 0.17 ×
1H), 6.73 (s, 0.83 × 1H), 7.15-7.38 (m, 3H), 7.60 (d, J ) 7.5
Hz, 2H); 13C NMR (CDCl3) for major isomer δ 14.1, 22.7, 28.8,
29.2, 29.3, 29.5, 29.55, 29.58, 29.61, 29.62, 29.9, 31.9, 57.5, 76.4,
127.1, 128.0, 129.4, 129.7, 132.9, 136.3. Found: C, 75.74; H,
10.18. Calcd for C22H36OS: C, 75.80; H, 10.41.
4-(2-Dodecylthioethenyl)benzonitrile (1i, E/Z ) 70:30):
IR (Nujol) 2922, 2853, 2228, 1591, 1468, 1377, 1177, 937, 854,
829, 789, 721, 646, 550, 502, 488 cm-1; 1H NMR (CDCl3) δ 0.89
(t, J ) 7.0 Hz, 3H), 1.20-1.47 (m, 18H), 1.70 (tt, J ) 7.5, 7.5
Hz, 2H), 2.84 (t, J ) 7.5 Hz, 0.70 × 2H), 2.83 (t, J ) 7.5 Hz,
0.30 × 2H), 6.38 (d, J ) 15.5 Hz, 0.70 × 1H), 6.40 (d, J ) 11.0
Hz, 0.30 × 1H), 6.50 (d, J ) 11.0 Hz, 0.30 × 1H), 6.94 (d, J )
15.5 Hz, 0.70 × 1H), 7.34 (d, J ) 8.5 Hz, 0.70 × 2H), 7.56 (d,
J ) 8.5 Hz, 2H), 7.62 (d, J ) 8.5 Hz, 0.30 × 2H); 13C NMR
(CDCl3) for major isomer δ 14.1, 22.7, 28.8, 29.1, 29.2, 29.3,
29.5, 29.55, 29.60, 29.62, 31.9, 32.4, 109.4, 119.1, 123.5, 125.6,
130.9, 132.5, 141.5. Found: C, 76.48; H, 9.27. Calcd for C21H31-
NS: C, 76.54; H, 9.48. Mp: 42.5-43.5 °C (amorphous solid).
(Z)-2-Dodecylthio-3-phenyl-2-propen-1-ol (1s): IR (Nu-
jol) 3285, 2922, 2853, 1591, 1464, 1445, 1377, 1115, 1101, 972,
849, 752, 691 cm-1 1H NMR (CDCl3) δ 0.88 (t, J ) 6.8 Hz,
;
3H), 1.18-1.37 (m, 18H), 1.55 (tt, J ) 7.5, 7.5 Hz, 2H), 1.94
(s, 1H), 2.76 (t, J ) 7.5 Hz, 2H), 4.36 (s, 2H), 6.82 (s, 1H), 7.25
(t, J ) 7.5 Hz, 1H), 7.35 (dd, J ) 7.5, 7.5 Hz, 2H), 7.60 (d, J )
7.5 Hz, 2H); 13C NMR (CDCl3) δ 14.1, 22.6, 28.7, 29.1, 29.3,
29.4, 29.5, 29.56, 29.57, 29.8, 31.3, 31.9, 66.9, 127.3, 128.0,
129.3, 129.8, 135.6, 136.1. Found: C, 75.16; H, 10.11. Calcd
for C21H34OS: C, 75.39; H, 10.24. Mp: 38.0-39.5 °C (amor-
phous solid).
Methyl 3-(2-dodecylthioethenyl)benzoate (1j, E/Z ) 13:
87): IR (neat) 2924, 2853, 1724, 1578, 1421, 1277, 1177, 1109,
1086, 999, 762, 747, 673 cm-1; 1H NMR (CDCl3) δ 0.88 (t, J )
7.0 Hz, 3H), 1.20-1.47 (m, 18H), 1.70 (tt, J ) 7.5, 7.5 Hz, 2H),
2.80 (t, J ) 7.5 Hz, 0.87 × 2H), 2.82 (t, J ) 7.5 Hz, 0.13 ×
2H), 3.92 (s, 0.13 × 3H), 3.93 (s, 0.87 × 3H), 6.35 (d, J ) 11.0
Hz, 0.87 × 1H), 6.45 (d, J ) 15.5 Hz, 0.13 × 1H), 6.46 (d, J )
11.0 Hz, 0.87 × 1H), 6.84 (d, J ) 15.5 Hz, 0.13 × 1H), 7.36
(dd, J ) 8.0, 8.0 Hz, 0.13 × 1H), 7.43 (dd, J ) 8.0, 8.0 Hz, 0.87
× 1H), 7.45 (d, J ) 8.0 Hz, 0.13 × 1H), 7.72 (d, J ) 8.0 Hz,
0.87 × 1H), 7.84 (d, J ) 8.0 Hz, 0.13 × 1H), 7.87 (d, J ) 8.0
Hz, 0.87 × 1H), 7.97 (s, 0.13 × 1H), 8.12 (s, J ) 0.87 × 1H);
13C NMR (CDCl3) for major isomer δ 14.1, 22.7, 28.5, 29.2, 29.3,
29.5, 29.55, 29.59, 29.61, 30.2, 31.9, 35.9, 52.1, 124.1, 127.4,
128.2, 129.3, 129.8, 130.1, 132.6, 137.3, 167.1. Found: C, 73.08;
H, 9.25. Calcd for C22H34O2S: C, 72.88; H, 9.45.
2-Dodecylthio-2-propen-1-ol (2a): IR (Nujol) 3213, 2922,
2853, 2729, 2332, 1605, 1468, 1377, 1298, 1217, 1126, 1067,
989, 856, 835, 762, 733, 719, 696, 638 cm-1; 1H NMR (CDCl3)
δ 0.88 (t, J ) 7.0 Hz, 3H), 1.20-1.45 (m, 18H), 1.61-1.71 (m,
3H), 2.74 (t, J ) 7.5 Hz, 2H), 4.18 (d, J ) 6.5 Hz, 2H), 4.93 (s,
1H), 5.36 (s, 1H); 13C NMR (CDCl3) δ 14.1, 22.7, 28.5, 29.0,
29.2, 29.3, 29.5, 29.57, 29.61, 29.63, 31.2, 31.9, 66.1, 108.0,
145.3. Found: C, 69.49; H, 11.40. Calcd for C15H30OS: C, 69.70;
H, 11.70. Mp: 43.0-44.0 °C (amorphous solid).
(Z)-3-Dodecylthio-2-propen-1-ol (2b): IR (Nujol) 3414,
2924, 2855, 1595, 1460, 1377, 1120, 1041, 721 cm-1; 1H NMR
(CDCl3) δ 0.88 (t, J ) 7.0 Hz, 3H), 1.20-1.48 (m, 19H), 1.62
(tt, J ) 7.5, 7.5 Hz, 2H), 2.67 (t, J ) 7.5 Hz, 2H), 4.62 (t, J )
6.5 Hz, 2H), 5.75 (dt, J ) 10.0, 6.5 Hz, 1H), 6.12 (d, J ) 10.0
Hz, 1H); 13C NMR (CDCl3) δ 14.1, 22.7, 28.5, 29.2, 29.3, 29.5,
29.57, 29.62, 29.63, 30.3, 31.9, 34.3, 60.0, 127.1, 128.4. Mp:
43.5-44.5 °C (amorphous solid).
(E)-3-Phenyl-2-propenyl styryl sulfide (1l, E/Z ) 8:92
with respect to the styryl moiety): IR (neat) 3024, 2918,
1597, 1491, 1443, 1418, 1362, 1225, 1074, 1028, 964, 910, 843,
3-Dodecylthio-3-buten-1-ol (2c): IR (neat) 3358, 2924,
1
773, 750, 729, 692 cm-1; H NMR (CDCl3) δ 3.58 (d, J ) 7.5
2853, 2683, 1603, 1466, 1439, 1377, 1148, 1047, 845, 721 cm-1
;
Hz, 2H), 6.21-6.30 (m, 2H), 6.47 (d, J ) 11.0 Hz, 0.92 × 1H),
1H NMR (CDCl3) δ 0.88 (t, J ) 7.0 Hz, 3H), 1.14-1.46 (m,
18H), 1.56-1.70 (m, 3H), 2.49 (t, J ) 6.0 Hz, 2H), 2.71 (t, J )
7.0 Hz, 2H), 3.75-3.83 (m, 2H), 4.80 (s, 1H), 5.11 (s, 1H); 13C
NMR (CDCl3) δ 13.8, 22.3, 27.8, 28.75, 28.83, 29.0, 29.1, 29.2,
29.26, 29.27, 31.0, 31.5, 40.6, 60.9, 107.1, 142.0. Found: C,
70.38; H, 11.60. Calcd for C16H32OS: C, 70.53; H, 11.84.
6.56 (d, J ) 15.5 Hz, 0.92 × 1H), 6.58 (d, J ) 16.0 Hz, 0.08 ×
1H), 6.74 (d, J ) 16.0 Hz, 0.08 × 1H), 7.15-7.50 (m, 10H); 13
C
NMR (CDCl3) for major isomer δ 37.6, 125.2, 125.6, 126.0,
126.4, 126.7, 127.8, 128.2, 128.58, 128.59, 133.1, 136.4, 136.9.
Found: C, 81.11; H, 6.50. Calcd for C17H16S: C, 80.90; H, 6.39.
Dodecyl 1,2-diphenylethenyl sulfide (1p, E/Z ) 15:85):
IR (neat) 3057, 3022, 2924, 2853, 1597, 1489, 1445, 1074, 1030,
939, 914, 764, 698, 669, 556, 509 cm-1; 1H NMR (CDCl3) δ 0.88
(t, J ) 7.0 Hz, 3H), 1.06-1.36 (m, 18H), 1.41 (tt, J ) 7.5, 7.5
Hz, 0.85 × 2H), 1.57 (tt, J ) 7.5, 7.5 Hz, 0.15 × 2H), 2.39 (t,
J ) 7.5 Hz, 0.85 × 2H), 2.52 (t, J ) 7.5 Hz, 0.15 × 2H), 6.72
(s, 0.15 × 1H), 6.79 (s, 0.85 × 1H), 6.91-7.75 (m, 10H); 13C
NMR (CDCl3) for major isomer δ 14.1, 22.7, 28.5, 29.0, 29.3,
29.4, 29.5, 29.61, 29.63, 29.8, 31.9, 32.8, 127.1, 127.8, 128.0,
128.30, 128.31, 129.6, 131.9, 137.1, 137.9, 141.2. Found: C,
82.12; H, 9.75. Calcd for C26H36S: C, 82.04; H, 9.53.
4-Dodecylthio-4-penten-1-ol (2d): IR (neat) 3348, 3092,
2924, 2853, 1601, 1466, 1441, 1377, 1205, 1148, 1042, 945, 908,
841, 721 cm-1 1H NMR (CDCl3) δ 0.88 (t, J ) 7.0 Hz, 3H),
;
1.13-1.44 (m, 19H), 1.64 (tt, J ) 7.5, 7.5 Hz, 2H), 1.82 (tt, J
) 7.5, 7.5 Hz, 2H), 2.33 (t, J ) 7.5 Hz, 2H), 2.70 (t, J ) 7.5
Hz, 2H), 3.64-3.72 (m, 2H), 4.72 (s, 1H), 5.06 (s, 1H); 13C NMR
(CDCl3) δ 14.0, 22.6, 28.1, 29.1, 29.1, 29.3, 29.4, 29.49, 29.54,
29.56, 31.2, 31.6, 31.8, 33.8, 62.0, 105.6, 145.3. Found: C,
71.53; H, 12.10. Calcd for C17H34OS: C, 71.26; H, 11.96.
5-Dodecylthio-5-hexen-1-ol (2f): IR (neat) 3350, 2924,
Dodecyl 1-methyl-2-phenylethenyl sulfide (1q, E/Z )
22:78): IR (neat) 3022, 2924, 2853, 1599, 1572, 1491, 1466,
1441, 1375, 1115, 1074, 1032, 910, 829, 748, 721, 694, 525
2855, 2685, 1601, 1466, 1439, 1377, 1142, 1063, 991, 841, 721
1
cm-1; H NMR (CDCl3) δ 0.88 (t, J ) 7.0 Hz, 3H), 1.13-1.70
(m, 25H), 2.58 (t, J ) 7.5 Hz, 2H), 2.69 (t, J ) 7.5 Hz, 2H),
3.62-3.72 (m, 2H), 4.69 (s, 1H), 5.02 (s, 1H); 13C NMR (CDCl3)
δ 14.01, 22.57, 24.79, 28.14, 29.04, 29.10, 29.23, 29.39, 29.47,
29.51, 29.53, 31.08, 31.79, 31.89, 37.18, 62.61, 105.22, 145.55.
Found: C, 71.84; H, 12.23. Calcd for C18H36OS: C, 71.93; H,
12.07.
1
cm-1; H NMR (CDCl3) δ 0.88 (t, J ) 7.0 Hz, 3H), 1.20-1.47
(m, 18H), 1.57 (tt, J ) 7.5, 7.5 Hz, 0.78 × 2H), 1.68 (tt, J )
7.5, 7.5 Hz, 0.22 × 2H), 2.12 (s, 0.22 × 3H), 2.22 (s, 0.78 ×
3H), 2.77 (t, J ) 7.5 Hz, 0.78 × 2H), 2.81 (t, J ) 7.5 Hz, 0.22
× 2H), 6.33 (s, 0.22 × 1H), 6.46 (s, 0.78 × 1H), 7.16-7.52 (m,
5H); 13C NMR (CDCl3) for major isomer δ 19.62, 19.63, 24.9,
28.9, 29.2, 29.3, 29.5, 29.56, 29.61, 29.62, 29.64, 30.0, 31.0,
126.3, 127.1, 127.9, 129.0, 132.8, 137.2. Found: C, 78.93; H,
10.63. Calcd for C21H34S: C, 79.18; H, 10.76.
(E)-3-Dodecylthio-1,2,3-triphenyl-2-propen-1-ol (7): IR
(Nujol) 3522, 2851, 1599, 1495, 1443, 1377, 1323, 1219, 1175,
1063, 1036, 926, 901, 854, 777, 752, 741, 700, 648, 600, 544
1
cm-1; H NMR (CDCl3) δ 0.88 (t, J ) 7.3 Hz, 3H), 1.01-1.35
2-Dodecylthio-3-phenyl-2-propenyl methyl ether (1r,
(m, 20H), 1.84 (d, J ) 7.0 Hz, 1H), 2.03-2.14 (m, 2H), 5.62 (d,
J ) 7.0 Hz, 1H), 6.91-6.70 (m, 2H), 7.01-7.05 (m, 2H), 7.14-
7.22 (m, 3H), 7.23-7.29 (m, 3H), 7.35-7.40 (m, 1H), 7.44-
7.49 (m, 2H), 7.52-7.56 (m, 2H); 13C NMR (CDCl3) δ 14.1, 22.7,
28.5, 29.0, 29.3, 29.4, 29.5, 29.6, 30.0, 31.8, 31.9, 73.7, 125.8,
E/Z ) 17:83): IR (neat) 2924, 2853, 2820, 1599, 1491, 1445,
1192, 1117, 1084, 1032, 914, 847, 752, 694 cm-1 1H NMR
;
(CDCl3) δ 0.88 (t, J ) 7.0 Hz, 3H), 1.18-1.40 (m, 18H), 1.56
(tt, J ) 7.5, 7.5 Hz, 2H), 2.81 (t, J ) 7.5 Hz, 0.83 × 2H), 2.83
(t, J ) 7.5 Hz, 0.17 × 2H), 3.39 (s, 0.17 × 3H), 3.41 (s, 0.83 ×
6472 J. Org. Chem., Vol. 70, No. 16, 2005