Abstract
Dicationic chiral Mn(III) salen complex (0.4 mol%) immobilized in the interlayer of montmorillonite clay 4A, epoxidize bulkier alkenes (epoxide yield 68–99%) with high chiral induction (up to 95% ee) with a catalyst reusability of up to four cycles.
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Viscous oil, 1H NMR (200 MHz, CDCl3) δ 12.00–11.00 (bs, 1H, exchangeable), 9.85 (s, 1H), 7.51 (d, J 1/4 2Hz; 1H), 7.33 (d, J 1/4 2Hz; 1H), 3.49 (s, 2H), 2.57 (m, 3H), 1.42 (s, 27H), 1.25–0.78 (m, 30 H); IR (KBr) cm 1 3378, 2959, 1722; Anal. Calcd. for C36H66ClNO2: C, 74.55; H, 11.39; N, 2.42 Found: C, 74.45, H, 11.30, N, 2.38.
Yield (94%); m.p. 105°C; (200 MHz, CDCl3) δ 14.0–13.7 (bs, 2H, exchangeable), 8.27 (s, 2H), 1.26 (bs, 2H), 7.19 (s, 10H), 6.8 (bs, 2H), 4.3 (s, 4H), 3.3 (bs, 2H), 2.5 (bs, 6H), 1.38–1.26 (bs, 60 H), 0.8 (s, 54 H); IR (KBr); 3378, 2959, 2873, 2454, 1648, 1442, 1268, 1231, 1160, 978, 893, 774, 710; Anal. Calcd. for C86H144Cl2N4O2: C, 77.30; H, 10.79; N, 4.20 Found: C, 77.27, H, 10.71, N, 4.18.
Complex 4: Yield (90%); m.p. 218°C Anal. Calcd. for C86H142Mn Cl3N4O2: C, 72.50; H, 9.98; N, 3.93. Found: C, 72.44; H, 9.92; N, 3.89; IR (KBr) cm 1 3446, 3062, 2955, 2869, 1607, 1532, 1344, 1312, 1169, 851; UV–vis. λmax nm (EtOH) 262 (14 500), 315 (14 600), 412 (4810); [α]D 27 = −105.41 (c =0.28, MeOH); configuration (S); μeff. (BM) 4.8; λM (MeOH), 109 mho cm−1 mol1.
Complex 4A: Calcd. C/N, 18.4, Found C/N, 19.6; IR (KBr), cm−1 3030, 2980, 2922, 1828, 1633, 1543, 1423, 1393, 1343; Solid reflectance λmax nm 262, 427sh, XRD (d001) = 13 å BET surface area 87 m2/g−1; pore diameter 94 å.
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FTIR, XRD and CHN analysis of the recovered catalyst showed partial degradation of the catalyst 4A and entrapment of reactant in the pores of clay matrix.
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Kureshy, R., Khan, N., Abdi, S. et al. Immobilization of Dicationic Mn(III) Salen in the Interlayers of Montmorillonite Clay for Enantioselective Epoxidation of Nonfunctionalized Alkenes. Catalysis Letters 91, 207–210 (2003). https://doi.org/10.1023/B:CATL.0000007156.16607.a8
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DOI: https://doi.org/10.1023/B:CATL.0000007156.16607.a8