562
T. AOYAMA ET AL.
2-Methyl-2-(4-nitrophenyl)-1,3-dithiolane (3bb)
Yellow solid. Mp 56 ꢀC. IR (neat): 2976, 2937, 1591, 1513, 1484, 1353, 1114,
1075, 858, 695 cmꢁ1
.
1H NMR (CDCl3): d ¼ 2.16 (3H, s), 3.31–3.41 (2H, m),
3.48–3.56 (2H, m), 7.91–7.95 (2H, m), 8.14–8.18 (2H, m). 13C NMR (CDCl3):
d ¼ 33.2, 40.6, 67.7, 123.2, 127.9, 146.7, 153.8. HRMS (TOF-CI): m=z [M þ H]þ
calcd. for C10H12NO2S2: 242.0309; found: 242.0299.
2-(4-Chlorophenyl)-2-methyl-1,3-oxathiolane (3ca)
IR (neat): 2975, 2939, 2876, 1488, 1397, 1267, 1133, 1093, 1068, 1047, 1013,
1
832, 800 cmꢁ1. H NMR (CDCl3): d ¼ 1.88 (3H, s), 3.04–3.10 (1H, m), 3.20–3.26
(1H, m), 3.97–4.03 (1H, m), 4.31–4.35 (1H, m), 7.26–7.31 (2H, m), 7.40–7.44 (2H,
m). 13C NMR (CDCl3): d ¼ 32.2, 34.5, 70.7, 95.0, 126.4, 128.2, 132.9, 145.4. HRMS
(TOF-CI): m=z [M þ H]þ calcd. for C10H12OSCl: 215.0297; found: 215.0291.
2-(4-Chlorophenyl)-2-methyl-1,3-dithiolane (3cb)
1
IR (neat): 2966, 2923, 1489, 1446, 1397, 1373, 1277, 1094, 1012, 832 cmꢁ1. H
NMR (CDCl3): d ¼ 2.12 (3H, s), 3.30–3.39 (2H, m), 3.42–3.48 (2H, m), 7.26 (2H, dd,
J ¼ 8.7, 2.5 Hz), 7.69 (2H, dd, J ¼ 8.7, 2.5 Hz). 13C NMR (CDCl3): d ¼ 33.5, 40.4,
67.9, 128.0, 128.3, 132.8, 144.6. HRMS (TOF-CI): m=z [M þ H]þ calcd. for
C10H12S2Cl: 231.0068; found: 231.0065.
2-(4-Methoxyphenyl)-2-methyl-1,3-oxathiolane (3da)
IR (neat): 2972, 2875, 2835, 1609, 1210, 1463, 1302, 1249, 2276, 1132, 1034
1
833 cmꢁ1. H NMR (CDCl3): d ¼ 1.89 (3H, s), 3.02–3.10 (1H, m), 3.15–3.24 (1H,
m), 3.78 (3H, s), 3.96–4.04 (1H, m), 4.27–4.34 (1H, m), 6.81–6.86 (2H, m),
7.39–7.45 (2H, m). 13C NMR (CDCl3): d ¼ 32.2, 34.3, 55.1, 70.4, 95.4, 113.3,
126.2, 138.7, 158.6. HR-MS (TOF-CI): m=z [M þ H]þ calcd. for C11H15O2S:
211.0792; found: 211.0790.
2-(4-Methoxy-phenyl)-2-methyl-1,3-dithiolane (3db)
IR (neat): 2960, 2923, 2834, 1607, 1508, 1463, 1297, 1251, 1180, 1033, 833,
1
735 cmꢁ1. H NMR (CDCl3): d ¼ 2.14 (3H, s), 3.34–3.50 (4H, m), 3.79 (3H, s),
6.83 (2H, dd, J ¼ 9.2, 2.8 Hz), 7.67 (2H, dd, J ¼ 9.2, 2.8 Hz). 13C NMR (CDCl3):
d ¼ 33.9, 40.4, 55.2, 68.1, 113.2, 128.1, 137.7, 158.5. HRMS (TOF-CI): m=z [M þ H]þ
calcd. for C11H15OS2: 227.0564; found: 227.0558.
2-Methyl-2-p-tolyl-1,3-oxathiolane (3ea)
IR (neat): 2974, 2924, 2875, 1510, 1441, 1370, 1267, 1133, 1093, 1069, 1047,
1
818 cmꢁ1. H NMR (CDCl3): d ¼ 1.90 (3H, s), 2.33 (3H, s), 3.03–3.10 (1H, m),
3.18–3.24 (1H, m), 3.98–4.05 (1H, m), 4.31–4.35 (1H, m), 7.13 (1H, d, J ¼ 8.0 Hz),
7.38 (1H, d, J ¼ 8.0 Hz). 13C NMR (CDCl3): d ¼ 21.0, 32.3, 34.4, 70.6, 95.6, 124.8,