Supplementary Data. Engineering, Nanjing University, Nanjing , P. R. China;
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- Ερατώ Ζάρκος
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1 Supplementary Data Synthesis, Chemo-selective Properties of Substituted 9-Aryl-9H-fluorenes from Triarylcarbinols and Enantiomerical Kinetics of Chiral 9-Methoxy-11-(naphthalen-1-yl)-11H-benzo[a]fluorene Ming-yu Teng* a,b, Ying Liu b, Shao-lu Li b, Guoli Huang a,b, Juli Jiang* b, and Leyong Wang* b a Facult of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming , P. R. China; mingyu_teng@hotmail.com b Key Laboratory of Mesoscopic Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing , P. R. China; jjl@nju.edu.cn; lywang@nju.edu.cn Contents I. General Procedure for Preparation of 1c, 1d, 1e, 1g, 1j, 1k... S2 II. General Procedure for Preparation of 1i... S5 III. NMR Spectral Characterization ( 1 H and 13 C NMR for 1c, 1d, 1e, 1g, 1i, 1j, 1k, 2a, 2b, 2c, 2d, 2e, 2f, and 2g)... S7 IV. Variable-temperature 1 H NMR and Eyring Plot Analysis of 2g and 2g... S21 V. EI-TF HRMS Spectra of 1d, 1e, 2a, and 2g... S23 VI. HPLC of 2g.... S25 VII. HMBC/HMQC 2D NMR Spectroscopy of 2g..... S26 Reference..... S29 S1
2 I. General Procedure for Preparation of 1c, 1d, 1e, 1g, 1h, 1k, 1l) (except 1i). [S1] R 3 R 1 Br Mg THF R 1 MgBr + R 3 CEt 1. THF H 2. H + R 1 R 2. R 1 = R 2 A mixture of bromoarene (32.0 mmol) and 20 ml of anhydrous THF is added to magnesium (2.30 g, 96.0 mmol), and the flask warmed gently until the reaction start. A mixture of bromoarene (64.0 mmol) and 40 ml of anhydrous THF is run in at such a rate as to cause vigorous refluxing, the mixture is warmed to refluxing for two hours, in order to dissolve all the magnesium. The reaction was cooled to room temperature, aromatic ester (40.0 mmol) is added into the Grinard solution, and the mixture is warmed to reflux over night. The reaction mixture is cooled in an ice-salt bath and then added slowly, with constant stirring, into 60 ml saturated NH 4 Cl aqueous solution. The mixture is distilled to remove THF and stream-distilled to remove biphenyl and unchanged bromobenzene. The product is filtered, washed with water, and recrystallized from ethanol and water. (4-Bromophenyl)bis(3-methoxyphenyl)methanol (1c) 5' 6' 2 3 3' 4' 2' H 6 5 Br Colorless solid; m.p ºC; R f = 0.43 (petroleum ether/ethyl acetate = 4/1); product 1.41 g (yield 35.3%). 1 H NMR (300M Hz, CDCl 3, TMS): δ = 7.42 (d, 2H, J = 8.7 Hz; H-3, 5), 7.23 (t, 2H, J = 8.7 Hz; H-5 ), 7.18 (d, 2H, J = 8.7 Hz; H-2, 6), 6.84 (s, 2H; H-2 ), (m, 4H; H-4, 6 ), 3.75 (s, 6H; H-3 ). 13 C NMR (75M Hz): δ = 159.2, 147.8, 145.5, 130.1, 129.6, 129.0, 121.4, 120.3, 113.8, 112.5, 81.5, FT-IR (cm -1 ): ν max (KBr/cm -1 ), 3554, 2969, 1597, 1484, 1421, 1321, 1286, 1251, 1166, 1137, 1072, 1042, 1022, 1010, 934, 865, 833, 775, 704. Anal. Calc. for C 21 H 19 Br 3 : C, 63.17; H, Found: C, 63.13; H, (2,5-Dichlorophenyl)bis(3-methoxyphenyl)methanol (1d) 5' 6' 6 Cl 3' 4' 2' H Cl 3 4 S2
3 Colorless solid; m.p ºC; R f = 0.53 (petroleum ether/ethyl acetate = 4/1); product 6.59 g (yield 42.3%). 1 H NMR (300M Hz, CDCl 3, TMS): δ = 7.32 (d, 1H, J = 8.4 Hz; H-3), 7.24 (t, 2H, J = 8.4 Hz; H-5 ), 7.23 (dd, 1H, J = 8.4, 2.1 Hz; H-4), 6.89 (t, 2H, J = 2.1 Hz; H-2 ), 6.85 (dd, 2H, J = 8. 4, 2.1 Hz; H-4 ), 6.76 (d, 2H, J = 8.4 Hz; H-6 ), 6.74 (d, 2H, J = 2.1 Hz, H-6), 3.78 (s, 6H; H-3 ). 13 C NMR (75M Hz): δ = 159.4, 146.2, 145.3, 132.5, 132.2, 131.4, 131.3, 129.0, 120.1, 113.4, 112.8, 82.1, FT-IR (cm -1 ): max (KBr/cm -1 ), 3445, 2956, 1599, 1559, 1487, 1457, 1289, 1250, 1105, 1047, 776, 758, 699, 553. HRMS (EI): m/z calcd for C 21 H 18 Cl 2 3 [M + ]: ; found: Bis(3-methoxyphenyl)(naphthalen-1-yl)methanol (1e) 5' 6' 2 3 3' 4' 2' H Colorless solid; m.p ºC; R f = 0.42 (petroleum ether/ethyl acetate = 4/1); product 6.04 g (yield 62.7%). 1 H NMR (300M Hz, CDCl 3, TMS): δ = 8.11 (d, 1H, J = 8.7 Hz; H-8), (m, 2H; H-4, 5), 7.39 (td, 1H, J = 8.8, 0.9 Hz; H-6), (m, 1H; naphthalen H), 7.22 (t, 2H, J = 8.1 Hz; H-5 ) (m, 1H; naphthalen H), 6.95 (t, 2H, J = 2.1 Hz; H-2 ), 6.88 (dd, 2H, J = 7.5, 0.9 Hz; naphthalen H), (m, 3H; H-6, naphthalen 2-H), 3.74 (s, 6H; H-3 ). 13 C NMR (75M Hz): δ = 159.3, 148.4, 141.7, 134.8, 131.1, 129.3, 128.9, 128.1, 127.8, 125.6, 125.2, 124.2, 120.3, 113.6, 113.5, 112.3, 83.1, FT-IR (cm -1 ): ν max (KBr/cm -1 ), 3454, 2935, 1597, 1486, 1463, 1432, 1316, 1289, 1250, 1143, 1040, 865, 781, 760, 700. HRMS (EI): m/z calcd for C 25 H 22 3 [M] + : ; found: (3-Methoxyphenyl)dinaphthalen-1-ylmethanol (1g) H 8 6' 2' 5' 4' 3' 6 7 Colorless solid; m.p. = ºC; R f = 0.63 (petroleum ether/ethyl acetate = 4/1); product 4.06 g (yield 52.1%).. S3
4 1 H NMR (300M Hz, CDCl 3, TMS): δ = 8.26 (brs), 2H; H-8), 7.87 (d, 2H, J = 8.1 Hz; H-5), 7.80 (d, 2H, J = 8.1 Hz; H-4), 7.41 (td, 2H, J = 7.5, 0.9 Hz; H-6), 7.28 (t, 2H, J = 7.5 Hz; H-7), (m, 3H, H-3, 5 ), 7.05 (s, 1H; H-2 ), (m, 4H, H-2, 4 6 ), 3.75 (s, 6H; H-3 ). 13 C NMR (75M Hz): 159.4, 148.6, 141.9, 135.0, 131.2, 129.4, 129.2, 128.9, 128.8, 128.4, 128.2, 125.5, 124.3, 120.5, 113.9, 112.1, 85.1, FT-IR (cm -1 ): ν max (KBr/cm -1 ), 3412, 3043, 1582, 1504, 1482, 1434, 1393, 1284, 1237, 1160, 1019, 875, 833, 806, 793, 776, 698, 560. Anal. Calc. for C 28 H 22 2 : C, 86.13; H, Found: C, 86.21; H, phenylbis(3-(trifluoromethyl)phenyl)methanol (1j) F 3 C 5' 6' 2 3 4' F 3 C 2' H Colorless oil; R f = 0.30 (petroleum ether/ethyl acetate = 10/1); product 1.68 g (yield 42.4%). 1 H NMR (300M Hz, CDCl 3, TMS): δ = 7.68 (s, 2H, H-2 ), 7.57 (d, 2H; J = 6.3 Hz; H-4 ), (m, 4H; H-5, 6 ), 7.36 (m, 1H; H-4), 7.34 (d, 2H, J = 2.4 Hz; H-2, 6) (m, 2H; H-3, 5), 2.91 (s, 1H; -H). 13 C NMR (75M Hz): δ = 146.1, 144.5, 130.3, (t, J = 31.9), 127.5, 127.5, 127.1, 126.7, 124.9, 123.4, 123.3, 121.3, FT-IR (cm -1 ): ν max (KBr/cm -1 ), 3454, 3076, 2926, 1492, 1446, 1330, 1168, 1120, 1076, 806, 703, 675. Anal. Calc. for C 21 H 14 F 6 : C, 63.64; H, Found: C, 63.69; H, (3-methoxyphenyl)bis(3-(trifluoromethyl)phenyl)methanol (1k) 5' F 3 C 6' 2 3 Me 4' F 3 C 2' H Colorless solid; m.p. = ºC; R f = 0.43 (petroleum ether/ethyl acetate = 10/1); product 1.59 g (yield 37.3%). 1 H NMR (300M Hz, CDCl 3, TMS): δ = 7.68 (s, 2H, H-2 ), 7.57 (d, 2H; J = 6.3 Hz; H-4 ), (m, 4H; H-5, 6 ), 7.27 (t, 1H; J = 8.1 Hz; H-5), 6.87 (dd, 1H, J = 8.1, 2.1 Hz; H-4), 6.78 (t, 1H; J = 2.1 Hz; H-2), 6.75 (d, 1H; J = 7.5 Hz; H-6), 3.75 (s, 3H; -Me), 2.92 (s, 1H; -H). S4
5 13 C NMR (75M Hz): δ = 159.6, 147.2, 147.0, 131.3, (t, J = 31.7), 129.6, 128.8, 128.6, 124.5, , 114.0, 113.1, 81.4, FT-IR (cm -1 ): ν max (KBr/cm -1 ), 3507, 2955, 1597, 1489, 1470, 1437, 1330, 1255, 1164, 1123, 1076, 1034, 809, 771, 705. Anal. Calc. for C 22 H 16 F 6 2 : C, 61.98; H, Found: C, 61.93; H, II. Procedure for Preparation of 1i A mixture of 1-bromo-3-(trifluoromethyl)benzene (4.95, 22.0 mmol) and 40 ml of anhydrous THF is added one third to magnesium (0.53g, 22.0 mmol), and the flask warmed gently until the reaction start. The residual mixture of benzophenone and anhydrous THF is run in at such a rate as to cause vigorous refluxing, the mixture is warmed to refluxing for two hours, in order to dissolved all the magnesium. The reaction was cooled to room temperature, 20.0 mmol of benzophenone is added into the Grinard solution, the mixture is warmed to reflux over night. The reaction mixture is cooled in an ice-salt bath and then added slowly, with constant stirring, into 16 ml saturated NH 4 Cl aqueous solution. The mixture is distilled to remove THF and stream-distilled to remove biphenyl and unchanged bromobenzene. The crude product was purified by column chromatography with silica gel using CH 2 Cl 2 as eluant to afford pure product. diphenyl(3-(trifluoromethyl)phenyl)methanol (1i) Colorless oil; R f = 0.41 (petroleum ether/ethyl acetate = 10/1); product 2.71g (yield 41.3 %). 1 H NMR (300M Hz, CDCl 3, TMS): δ = 7.75 (s, 1H, H-2 ), 7.58 (d, 1H; J = 7.8 Hz; H-4 ), (m, 2H; H-5, 6 ), (m, 10H; H-2, 3, 4, 5, 6), 2.98 (s, 1H; -H). 13 C NMR (75M Hz): δ = 147.9, 146.3, 131.5, 128.9, 128.8, 128.3, 127.9, 127.7, 124.5, 124.5, 124.2, 124.1, FT-IR (cm -1 ): ν max (KBr/cm -1 ), 3449, 2925, 2855, 1448, 1167, 1128, 1076, 1018, 804, 755, 702, 661. Anal. Calc. for C 20 H 15 F 3 : C, 73.16; H, Found: C, 73.07; H, References [S1] Bachmann, W. E., Hetzner, H. P. rg. Synth. 1955, Coll. Vol. 3, 839. S5
6 III. NMR Spectral Characterization ( 1 H and 13 C NMR for 1c, 1d, 1e, 1g, 1i, 1j, 1k, 2a, 2b, 2c, 2d, 2e, 2f, 2g, and 3a) 1c in CDCl Br Me Me water H Br S6
7 1d in CDCl Cl Cl H EtH EtH Cl H Cl S7
8 1e in CDCl H S8
9 1g in CDCl H S9
10 1i in CDCl H F 3 C S10
11 1j in CDCl F 3 C H CF water petroleum F 3 C H CF S11
12 1k in CDCl F 3 C H CF S12
13 2a in CDCl S13
14 2b in CDCl 3 0,02 3,78 3,79 4,02 4,96 6,83 6,83 6,89 6,90 6,92 6,93 7,09 7,10 7,12 7,13 7,26 7,26 7,27 7,29 7,59 7,61 Me Me Me Me S14
15 2c in CDCl 3 S15
16 2d in CDCl Cl Cl Cl Cl S16
17 2e in CDCl S17
18 2f in CDCl S18
19 2g in CDCl S19
20 2g in DMS-d Me DMS water g in benzene-d S20
21 IV. Variable-temperature 1 H NMR and Eyring Plot Analysis of 2g and 2g (300 MHz, DMS) 393 K 388 K 383 K 378 K 373 K 363 K 338 K 297 K S21
22 ln(k)\ln(k/t) Electronic Supplementary Material (ESI) for RSC Advances T (K) rate constant k/s -1 1/T (K -1 ) 1/T 1000 ln(k) ln(k/t) ΔG (J/mol) 3.630E E E E E E E E E E E E E E E E E E E E E E E E+04 1/T - ln(k)\ln(k/t) E E E E-03 1/T ln(k) = *1/T E E-03 R 2 = E-03 ln(k) ln(k/t) = *1/T R 2 = ln(k/t) R 8.314E+0 ln(k)=lna-ea/rt Ea/R Ea (J/mol) E+3 -ΔH / R E+04 ln(k/t) = ΔS /8.31- ΔH /(8.31T) ΔH (J/mol) ΔG =(23.76-ln(k/T))*R*T ΔG =at( log(k/t)) a=1.914*0.01 (ΔG in kj/mol) a=1.914*10 (ΔG in J/mol) ΔG =ΔH -TΔS ΔS (J/mol*K) (T = 373K) S22
23 V. MS Spectra 1d 1e S23
24 2a 2g S24
25 VI. HPLC of 2g. S25
26 VII. H-HCSY/HMBC/HMQC 2D NMR Spectroscopy of 2g (500M Hz, in CDCl 3 ). S26
27 S27
28 S28
29 Reference [S1]. Bachmann, W. E.; Hetzner H. P. rg. Synth. 1955, Coll. Vol. 3, S29
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