A. Kondoh et al. / Tetrahedron 62 (2006) 2357–2360
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4.2.2. 2-Dodecylthiobenzaldehyde (3b). IR (neat) 2924,
2853, 2731, 1695, 1587, 1560, 1460, 1439, 1396, 1261,
(m, 2H), 7.72 (d, JZ8.0 Hz, 2H), 9.91 (s, 1H); 13C NMR
(CDCl3) d 127.10, 129.14, 129.77, 130.09, 131.16, 133.59,
134.34, 147.23, 191.18. Found: C, 72.64; H, 4.83%. Calcd
for C13H10OS: C, 72.87; H, 4.70%.
1
1196, 1128, 750 cmK1; H NMR (CDCl3) d 0.88 (t, JZ
7.0 Hz, 3H), 1.21–1.35 (m, 16H), 1.45 (tt, JZ7.5, 7.5 Hz,
2H), 1.70 (tt, JZ7.5, 7.5 Hz, 2H), 2.95 (t, JZ7.5 Hz, 2H),
7.30 (dd, JZ7.0, 7.5 Hz, 1H), 7.42 (d, JZ8.0 Hz, 1H), 7.51
(dd, JZ7.0, 8.0 Hz, 1H), 7.84 (d, JZ7.5 Hz, 1H), 10.39 (s,
1H); 13C NMR (CDCl3) d 14.09, 22.64, 28.48, 28.93, 29.12,
29.30, 29.43, 29.53, 29.57, 29.59, 31.86, 33.18, 125.09,
127.97, 131.98, 133.82, 133.83, 142.30, 191.50. Found: C,
74.55; H, 9.95%. Calcd for C19H30OS: C, 74.45; H, 9.86%.
4.2.8. 4-(2-Propenylthio)benzaldehyde (3h). IR (neat)
2922, 2833, 2736, 1697, 1672, 1637, 1591, 1562, 1489,
1410, 1387, 1306, 1285, 1215, 1171, 1090, 989, 926, 837,
812, 739, 696, 536, 486 cmK1; 1H NMR (CDCl3) d 3.68 (d,
JZ6.5 Hz, 2H), 5.19 (d, JZ9.0 Hz, 1H), 5.31 (d, JZ
15.5 Hz, 1H), 5.91 (ddd, JZ6.5, 9.0, 15.5 Hz, 1H), 7.38 (d,
JZ6.5 Hz, 2H), 7.77 (d, JZ6.5 Hz, 2H), 9.93 (s, 1H); 13C
NMR (CDCl3) d 35.02, 118.68, 126.90, 129.91, 132.28,
133.34, 145.82, 191.24. Found: C, 67.26; H, 5.67%. Calcd
for C10H10OS: C, 67.38; H, 5.65%.
4.2.3. 1-Dodecylthio-4-nitrobenzene (3c). IR (Nujol)
2224, 2853, 2332, 2235, 1578, 1508, 1466, 1337, 1082,
962, 851, 837, 745, 723, 669, 617 cmK1; 1H NMR (CDCl3)
d 0.88 (t, JZ7.0 Hz, 3H), 1.20–1.38 (m, 16H), 1.46 (tt, JZ
7.5, 7.5 Hz, 2H), 1.72 (tt, JZ7.5, 7.5 Hz, 2H), 3.01 (t, JZ
7.5 Hz, 2H), 7.31 (d, JZ9.5 Hz, 2H), 8.12 (d, JZ9.5 Hz,
2H); 13C NMR (CDCl3) d 14.11, 22.67, 28.44, 28.86, 29.09,
29.32, 29.44, 29.53, 29.60, 29.61, 31.89, 31.90, 123.91,
125.93, 144.79, 148.17. Found: C, 66.68; H, 8.96%. Calcd
for C18H29NO2S: C, 66.83; H, 9.04%. Mp 49.5–50.5 8C.
4.2.9. 4-[(E)-3-Phenyl-2-propenylthio]benzaldehyde (3i).
IR (Nujol) 2924, 2855, 2731, 1696, 1589, 1560, 1460, 1377,
1
1084, 1028, 966, 837, 814, 762, 745, 698 cmK1; H NMR
(CDCl3) d 3.85 (d, JZ7.0 Hz, 2H), 6.26 (dt, JZ16.0,
7.0 Hz, 1H), 6.62 (d, JZ16.0 Hz, 1H), 7.22–7.37 (m, 5H),
7.42 (d, JZ8.0 Hz, 2H), 7.77 (d, JZ8.0 Hz, 2H), 9.93 (s,
1H); 13C NMR (CDCl3) d 34.95, 123.56, 126.38, 127.16,
127.90, 128.60, 130.01, 133.47, 133.73, 136.25, 145.81,
191.27. Found: C, 75.29; H, 5.53%. Calcd for C16H14OS: C,
75.56; H, 5.55%. mp 91.0–92.5 8C.
4.2.4. 4-Dodecylthioacetophenone (3d). IR (Nujol) 2920,
2851, 2345, 1678, 1591, 1462, 1377, 1364, 1053, 976, 816,
719, 590 cmK1; 1H NMR (CDCl3) d 0.88 (t, JZ7.0 Hz, 3H),
1.20–1.36 (m, 16H), 1.45 (tt, JZ7.5, 7.5 Hz, 2H), 1.70 (tt,
JZ7.5, 7.5 Hz, 2H), 2.57 (s, 3H), 2.99 (t, JZ7.5 Hz, 2H),
7.30 (d, JZ9.0 Hz, 2H), 7.86 (d, JZ9.0 Hz, 2H); 13C NMR
(CDCl3) d 14.12, 22.68, 26.44, 28.70, 28.89, 29.13, 29.33,
29.46, 29.55, 29.61, 29.62, 31.89, 31.90, 126.16, 128.72,
133.63, 145.01, 197.21. Found: C, 74.76; H, 9.87%. Calcd
for C20H32OS: C, 74.94; H, 10.06%. Mp 69.5–70.2 8C.
4.2.10. 4-(1,1-Dimethylethylthio)benzaldehyde (3j). IR
(neat) 2963, 2924, 2899, 2862, 2831, 2729, 1705, 1593,
1562, 1474, 1458, 1366, 1298, 1281, 1205, 1167, 1086,
1016, 826, 718, 698, 503 cmK1; 1H NMR (CDCl3) d 1.34 (s,
9H), 7.69 (d, JZ8.0 Hz, 2H), 7.83 (d, JZ8.0 Hz, 2H), 10.04
(s, 1H); 13C NMR (CDCl3) d 31.05, 47.10, 129.37, 135.77,
136.97, 141.20, 191.66. Found: C, 68.28; H, 7.31%. Calcd
for C11H14OS: C, 68.00; H, 7.26%.
4.2.5. Methyl 4-dodecylthiobenzoate (3e). IR (Nujol)
2918, 2851, 1724, 1678, 1599, 1462, 1398, 1366, 1290,
1196, 1115, 1092, 831, 816, 754, 719, 691 cmK1; 1H NMR
(CDCl3) d 0.88 (t, JZ7.0 Hz, 3H), 1.20–1.35 (m, 16H), 1.44
(tt, JZ7.0, 7.5 Hz, 2H), 1.69 (tt, JZ7.0, 7.5 Hz, 2H), 2.98
(t, JZ7.5 Hz, 2H), 3.90 (s, 3H), 7.28 (d, JZ8.5 Hz, 2H),
7.92 (d, JZ8.5 Hz, 2H); 13C NMR (CDCl3) d 14.12, 22.68,
28.70, 28.88, 29.13, 29.33, 29.46, 29.55, 29.61, 29.62,
31.90, 31.99, 52.02, 126.18, 126.43, 129.86, 144.51, 166.85.
Found: C, 71.27; H, 9.41%. Calcd for C20H32O2S: C, 71.38;
H, 9.58%. Mp 64.5–65.2 8C.
4.2.11. Methyl 4-(2-hydroxyethylthio)benzoate (3k). IR
(Nujol) 3344, 2924, 2855, 1720, 1597, 1460, 1377, 1281,
1115, 1057, 1013, 959, 758 cmK1; 1H NMR (CDCl3) d 2.11
(s, 1H), 3.20 (t, JZ6.5 Hz, 2H), 3.82 (t, JZ6.5 Hz, 2H), 3.89
(s, 3H), 7.34 (d, JZ9.0 Hz, 2H), 7.92 (d, JZ9.0 Hz, 2H); 13C
NMR (CDCl3) d 35.37, 52.10, 60.40, 127.20, 127.30, 130.01,
142.40, 166.67. Found: C, 56.44; H, 5.67%. Calcd for
C10H12O3S: C, 56.58; H, 5.70%. Mp 58.0–59.5 8C.
4.2.12. 1,3-Di(4-methoxycarbonylphenylthio)propane
(5). IR (Nujol) 2924, 2853, 1722, 1595, 1435, 1377, 1277,
1250, 1192, 1113, 1015, 961, 847, 829, 756, 692 cmK1; 1H
NMR (CDCl3) d 2.06 (quint, JZ7.0 Hz, 2H), 3.14 (t, JZ
7.0 Hz, 4H), 3.90 (s, 6H), 7.29 (d, JZ9.0 Hz, 4H), 7.91 (d,
JZ9.0 Hz, 4H); 13C NMR (CDCl3) d 27.89, 31.05, 52.34,
127.02, 127.32, 130.26, 143.30, 166.94. Found: C, 60.36; H,
5.38%. Calcd for C19H20O4S2: C, 60.61; H, 5.35%. Mp
98.5–100.0 8C.
4.2.6. 4-Dodecylthiobenzonitrile (3f). IR (Nujol) 2918,
2851, 2230, 1919, 1593, 1547, 1487, 1470, 1431, 1402,
1379, 1346, 1302, 1244, 1182, 1126, 1089, 1070, 1015, 824,
779, 762, 719, 592, 544 cmK1; 1H NMR (CDCl3) d 0.88 (t,
JZ7.0 Hz, 3H), 1.21–1.36 (m, 16H), 1.44 (tt, JZ7.0,
7.5 Hz, 2H), 1.69 (t, JZ7.5, 7.5 Hz, 2H), 2.97 (t, JZ7.5 Hz,
2H), 7.29 (d, JZ8.5 Hz, 2H), 7.52 (d, JZ8.5 Hz, 2H); 13C
NMR (CDCl3) d 14.11, 22.67, 28.51, 28.84, 29.09, 29.32,
29.44, 29.53, 29.59, 29.61, 31.82, 31.88, 107.80, 118.98,
126.57, 132.16, 145.31. Found: C, 75.12; H, 9.50%. Calcd
for C19H29NS: C, 75.19; H, 9.63%. Mp 50.0–50.5 8C.
4.2.13. N-Acetyl-S-(4-methoxycarbonylphenyl)-L-cysteine
(6). IR (Nujol) 3337, 2924, 2855, 2532, 2104, 1715, 1618,
1597, 1560, 1491, 1458, 1439, 1377, 1277, 1232, 1186, 1109,
1013, 758 cmK1; 1H NMR (CD3OD) d 1.90 (s, 3H), 3.26–3.36
(m, 1H), 3.54–3.64 (m, 1H), 3.88 (s, 3H), 4.60–4.66 (m, 1H),
7.43 (d, JZ8.7 Hz, 2H), 7.91 (d, JZ8.7 Hz, 2H); 13C NMR
(CD3OD) d 22.35, 34.84, 52.60, 53.37, 128.40, 128.48,
130.81, 144.11, 167.88, 172.82, 173.05. Found: C, 52.37; H,
4.2.7. 4-Phenylthiobenzaldehyde (3g). IR (neat) 3059,
2831, 2735, 1699, 1670, 1593, 1562, 1475, 1441, 1387,
1358, 1302, 1285, 1211, 1169, 1078, 1024, 1013, 1001, 920,
1
837, 816, 750, 692, 507, 478 cmK1; H NMR (CDCl3) d
7.24 (d, JZ8.0 Hz, 2H), 7.41–7.46 (m, 3H), 7.51–7.56