Highly regioselective ring-opening of epoxides with thiophenols in ionic liquids without the use of any catalyst

Green Chemistry

Volumn 8, Issue 4, 2006, Pages 330-332

  Chen, Jiuxi ^a   Wu, Huayue ^a   Jin, Can ^b   Zhang, Xingxian ^b   Xie, Yuanyuan ^b   Su, Weike ^a,b  

^a WENZHOU UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33645456496     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/b600620e     Document Type: Article

References (49)

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45. Representative procedure: To a mixture of 1,2-epoxy-3-phenoxypropane (300.4 mg, 2 mmol) and 4-thiocresol (248 mg, 2 mmol), [Emim]BF4 (1 mL) was added. The mixture was stirred at 50 °C for 10 min. After completion of the reaction, as indicated by TLC, the reaction mixture was extracted with diethyl ether (3 × 10 mL). The combined ether extracts were concentrated in vacuo and the crude product 1b was obtained. The corresponding purified form was obtained by flash column chormatography. Selected data for compounds 1e: Rf = 0.4 (petroleum ether/EtOAc = 6 : 1); 1H NMR (400 MHz, CDCl3): δ (ppm) = 7.33 (d, J = 8.0 Hz, 2 H), 7.27–7.20 (m, 4 H), 6.95 (t, J = 7.2 Hz, 1 H), 6.84 (d, J = 8.0 Hz, 2 H), 4.08–3.98 (m, 3 H), 3.19 (dd, J = 13.6, 5.6 Hz, 1 H), 3.12 (br s, 1 H, OH), 3.09 (dd, J = 13.6, 6.8 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ (ppm) = 158.0, 134.4, 131.9, 130.9, 129.4, 121.1, 120.2, 114.3, 69.7, 68.4, 37.2. IR (neat): 3418, 3061, 2925, 1599, 1496, 1474, 1243, 1091, 1007, 810, 754, 691 cm−1. m/z (EI) 340 ([M + 2]+, 88), 340 (M+, 100), 247 (33), 245 (36), 229 (23), 227 (18), 33 (36). Found: C, 53.19; H, 4.50. Anal. calcd for C15H15BrO2S: C, 53.11; H, 4.46. 1n: Rf = 0.4 (petroleum ether/EtOAc = 6 : 1); 1H NMR (400 MHz, CDCl3): δ (ppm) = 7.41–7.38 (m, 2 H), 7.00 (t, J = 8.4 Hz, 2 H), 3.85–3.77 (m, 1 H), 3.04 (dd, J = 13.6, 3.6 Hz, 1 H), 2.81 (dd, J = 13.6, 8.4 Hz, 1 H), 2.67 (br s, 1 H, OH), 1.25 (d, J = 6.4 Hz, 3 H). 13C NMR (100 MHz, CDCl3): δ (ppm) = 162.0 (d, 1JCF = 245.7 Hz), 133.0 (d, 3JCF = 8.3 Hz), 130.0, 116.1 (d, 2JCF = 21.2 Hz), 65.4, 44.7, 21.8. IR (neat): 3404, 2971, 2926, 1590, 1491, 1456, 1228, 1157, 1090, 824, 629 cm−1. m/z (EI) 186 (M+, 100), 169 (77), 141 (13). Found: C, 58.12; H, 5.86. Anal. calcd for C9H11FOS: C, 58.04; H, 5.95. 1s: Rf = 0.4 (petroleum ether/EtOAc = 6 : 1); 1H NMR (400 MHz, CDCl3): δ (ppm) = 7.32–7.35 (m, 2 H), 7.21–7.10 (m, 1 H), 4.04–3.98 (m, 1 H), 3.72 (d, J = 4.8 Hz, 2 H), 3.22 (dd, J = 14.0, 5.6 Hz, 1 H), 3.12 (dd, J = 14.0, 6.8 Hz, 1 H), 2.83 (br s, 1 H, OH). 13C NMR (100 MHz, CDCl3): δ (ppm) = 137.0, 133.7, 131.7, 127.9, 127.5, 126.6, 69.3, 48.0, 36.8. IR (neat): 3388, 2955, 2923, 1565, 1435, 1399, 1043, 767, 697 cm−1. m/z (EI) 276 ([M + 6]+, 5), 274 ([M + 4]+, 33), 272 ([M + 2]+, 94), 270 (M+, 100), 255 (42), 253 (48), 193 (46), 191 (74), 142 (31). Found: C, 39.86; H, 3.26. Anal. calcd for C9H9Cl3OS: C, 39.80; H, 3.34.
46. The reagents were purchased from Shanghai KeLy Bio-Pharmaceutical Co., Ltd., (a) the optical purity is 99%; (b) the optical purity is 98%.
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