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Typical Experimental Procedure: Propylene oxide (20 mmol, L-phenylalanine (0.16 mmol) and CH2Cl2 (1 mL) were added into a 15 mL stainless autoclave with a magnetic stirrer, and CO 2 (liquid, 3.2 MPa) was charged into the reactor at r.t. The initial pressure was generally adjusted to 6 MPa at 130°C. The autoclave was heated at that temperature for 48 h, and the pressure was kept constant during the reaction. After the reaction, the reactor was cooled to 0°C, and extra CO2 was vented slowly. The crude product was analyzed by a gas chromatograph, compared with authentic sample, and the yields were determined by GC using tridecane as internal standard. The crude product (yield: 100% by GC) was purified by distillation and propylene carbonate was obtained in 93% isolated yield. The cyclic carbonate was identified by IR, GC/MS (HP6890/ 5973) and 400 MHz NMR spectroscopy
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2 was vented slowly. The crude product was analyzed by a gas chromatograph, compared with authentic sample, and the yields were determined by GC using tridecane as internal standard. The crude product (yield: 100% by GC) was purified by distillation and propylene carbonate was obtained in 93% isolated yield. The cyclic carbonate was identified by IR, GC/MS (HP6890/ 5973) and 400 MHz NMR spectroscopy.
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Spectroscopic data of the cyclic carbonates: 4-Methyl-1,3-dioxolan-2- one(2a, IR (neat, 1795 (C=O) cm-1. MS (EI, m/z, 102 [M, 1H NMR (400 MHz, TMS, CDCl3, δ, 1.48 (d, J, 3.6 Hz, 3 H, CH3, 4.01 (t, J, 8.4 Hz, 1 H, CH, 4.53 (t, J, 8.0 Hz, 1 H, CH, 4.81-4.86 (m, 1 H, CH, 4-Chloromethyl-1,3-dioxolan-2-one(2b, IR (neat, 1790 (C=O) cm -1. MS (EI, m/z, 136 [M, 1H NMR (400 MHz, TMS, CDCl3, δ, 3.72-3.74 (m, 2 H, CH2, 4.38 (q, J, 6.0 Hz, 1 H, CH, 4.57 (t, J, 8.4 Hz, 1 H, CH, 4.91-1.94 (m, 1 H, CH, 4-Phenyl-1,3-dioxolan-2-one (2c, IR (neat, 1816 (C=O) cm-1. MS (EI, m/z, 164 [M, 1H NMR (400 MHz, TMS, CDCl3, δ, 4.31-4.35 (m, 1 H, CH, 4.76-4.82 (m, 1 H, CH, 5.66 (t, J, 8.0 Hz, 1 H, CH, 7.32-7.44 m, 5 H, C
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2), 4.63-4.68 (m, 2 H, CH).
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