HETEROCYCLES, Vol. 90, No. 1, 2015
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3',3'-Diphenylspiro[5H-dibenzo[a,d]cyclohepten-5,4'-thietane]-2-one (3c). Yield: 298 mg (72%).
Colorless crystals, mp 167 °C (dec.). IR (KBr): 3022m, 2956m, 1748vs (C=O), 1705m, 1596m, 1492m,
1478m, 1436m, 1327m, 1186m, 1049m, 831s, 765m, 727s, 697s, 645m. 1H-NMR: 6.54 (s, 2 CH=); 6.99 (t,
JH,H = 7.4 Hz, 4 Harom); 7.03–7.10 (m, 8 Harom); 7.21 (t, JH,H = 7.4 Hz, 2 Harom); 7.41 (dt, JH,H = 7.6, 1.1 Hz,
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2 Harom); 8.02 (d, JH,H = 8.0 Hz, 2 Harom). C-NMR: 69.9, 93.3 (2 Cq); 126.8, 126.9, 127.3, 128.3, 128.4,
128.8, 130.8, 132.9 (18 CHarom, 2 CH=); 135.1, 136.4, 137.3 (4 Carom); 193.9 (C=O). Anal. Calcd for
C29H20OS (416.54): C 83.62; H 4.84; S 7.70. Found: C 83.75; H 4.91 S 7.82.
3',3'-Diphenylspiro[10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,4'-thietane]-2-one (3d). Yield: 279
mg (67%). Colorless crystals, mp 149 °C (dec.). IR (KBr): 3024m, 2981m, 1743vs (C=O), 1701m, 1597m,
1
1491m, 1478m, 1339m, 1162m, 1054m, 834s, 778m, 726s, 699s, 626m. H-NMR: 2.59–2.64 (m, 2 H,
CH2); 3.18–3.22 (m, 2 H, CH2); 6.87–6.89 (m, 2 Harom); 7.04–7.15 (m, 14 Harom); 7.98–8.00 (m, 2 Harom).
13C-NMR: 32.9 (2 CH2); 71.5, 94.2 (2 Cq); 126.1, 127.4, 127.6, 128.2, 129.9, 130.3, 130.4 (18 CHarom);
136.3, 139.0, 139.5 (6 Carom); 194.6 (C=O). Anal. Calcd for C29H22OS (418.65): C 83.22; H 5.30; S 7.66.
Found: C 83.35; H 5.27; S 7.71.
3,3,4-Triphenyl-4-(2-thienyl)thietan-2-one (3e). Yield: 270 mg (68%). Pale yellow crystals, mp 146 °C
(dec.). IR (KBr): 3059m, 3031m, 1735vs (C=O), 1598m, 1444s, 1236m, 1049m, 1000m, 827s, 753s, 699s.
1H-NMR: 6.59 (dd, JH,H = 3.8, 1.2 Hz, 1 Harom); 6.67 (dd, JH,H = 5.0, 3.8 Hz, 1 Harom); 7.04–7.10 (m, 6
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Harom); 7.21–7.28 (m, 8 Harom); 7.43–7.46 (m, 2 Harom). C-NMR: 62.4, 94.2 (2 Cq); 126.3, 126.9, 127.2,
127.6, 127.7, 127.9, 128.6, 129.2, 130.0, 130.2 (18 CHarom); 137.2, 138.5, 140.1, 150.8 (4 Carom); 193.5
(C=O). HR-ESI-MS (MeOH/CHCl3+NaOH): 421.06913 (calcd. 421.06902 for C25H18NaOS2 [M+Na]+).
3,3,4-Triphenyl-(4-selenophen-2-yl)thietan-2-one (3f). Yield: 290 mg (65%). Pale brown crystals, mp
163 °C (dec.). IR (KBr): 3059m, 3029m, 1733vs (C=O), 1596m, 1489s, 1334m, 1282m, 1158m, 1118m,
1088m, 1048m, 1000m, 827s, 719s, 647m. 1H-NMR: 6.75 (d, JH,H = 3.7 Hz, 1 Harom); 6.91 (dd, JH,H = 5.6,
4.0 Hz, 1 Harom); 7.03–7.11 (m, 5 Harom); 7.21–7.29 (m, 8 Harom); 7.49–7.50 (m, 2 Harom); 7.79 (d, JH,H
=
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5.6 Hz, 1 Harom). C-NMR: 64.3, 94.3 (2 Cq); 127.2, 127.3, 127.6, 127.7, 127.8, 127.9, 128.9, 129.0,
129.2, 130.0, 132.0, 133.1 (18 CHarom); 137.2, 138.6, 140.7, 159.1 (4 Carom); 193.6 (C=O). Anal. Calcd for
C25H18OSSe (445.44): C 67.41; H 4.07; S 7.20. Found: C 67.60; H 4.11; S 7.31.
4-(2-Furyl)-3,3-diphenyl-4-(2-thienyl)thietan-2-one (3g). Yield: 270 mg (70%). Yellow crystals, mp
136 °C (dec.). IR (KBr): 3039m, 3028m, 1746vs (C=O), 1599m, 1491s, 1375m, 1228m, 1156m, 1090m,
1044m, 1017m, 827s, 753s, 699s. 1H-NMR: 6.17 (dd, JH,H = 3.2, 1.8 Hz, 1 Harom); 6.24 (dd, JH,H = 3.2, 0.5
Hz, 1 Harom); 6.77 (dd, JH,H = 5.0, 3.7 Hz, 1 Harom); 6.88 (dd, JH,H = 3.6, 1.1 Hz, 1 Harom); 7.10–7.14 (m, 4