Aluminium triflate as a Lewis acid catalyst for the ring opening of epoxides in alcohols

Μέγεθος: px
Εμφάνιση ξεκινά από τη σελίδα:

Download "Aluminium triflate as a Lewis acid catalyst for the ring opening of epoxides in alcohols"

Transcript

1 Aluminium triflate as a Lewis acid catalyst for the ring opening of epoxides in alcohols D. Bradley G. Williams* and Michelle Lawton a Department of Chemistry, University of Johannesburg, P.O. Box 524, Auckland Park, 2006 Fax: +27(0) ; Tel: +27(0) ; dbgw@rau.ac.za Supplementary Information All compounds were determined to be >99% pure on the basis of GC-FID analyses (total peak area), taken together with clean NMR spectra, after isolation by column chromatography and/or vacuum distillation. Copies of three 13 C NMR spectra are included as examples. Regioisomers were distinguished on the basis of ghmbc and ghmqc NMR experiments. 2-Methoxy-2-phenylethanol, IR ν max (CHCl 3 ) 3398, 2870, 1452, 1355, 1063 cm H NMR (300 MHz; CDCl 3, TMSCl): δ 2.97 (s, 1H, OH), 3.29 (s, 3H, OCH 3 ), 3.59 (dd, J = 11.7, 8.4, 1H, CH 2B OH), 3.69 (dd, J = 11.7, 3.9, 1H, CH 2A OH), 4.3 (dd, J = 8.4, 3.9, 1H, CHOCH 3 ), (m, 5H, H-aromatic), 13 C NMR (300 MHz; CDCl 3 ): δ 56.7 (CH 3 ), 67.2 (CH 2 ), 84.8 (CH), (ortho), (para), (meta), (ipso); m/z (EI) 153 (M +, 5%), 135 (10), 121 (100). 2-Ethoxy-2-phenylethanol, IR ν max (CHCl 3 ) 3589,3011, 2978, 1101, 1032 cm H NMR (300 MHz; CDCl 3 ): δ 1.21 (t, J = 6.9, 3H, CH 3 ), 2.93 (br s, 1H, OH), (m, 2H, OCH 2 CH 3 ), 3.58 (dd, J = 11.7, 3.9, 1H, CH 2B OH), 3.66 (dd, J = 11.7, 8.4, 1H, CH 2A OH), 4.40 (dd, J = 8.4, 3.9, CHOCH 2 CH 3 ), (m, 5H, H-aromatic). 13 C NMR (300 MHz; CDCl 3 ): δ 15.1 (CH 3 ), 64.3 (CH 2 CH 3 ), 67.1 (CH 2 OH), 82.8 (CHOCH 2 CH 3 ), (ortho), (para), (meta), (ipso); m/z (EI) 149 (M +, 10%), 135 (100), 107 (60), 79 (60). 2-Phenyl-2-propoxyethanol, IR ν max (CHCl 3 ) 3588, 2965, 2878, 1101, 1031 cm H NMR (300 MHz; CDCl 3 ): δ 0.92 (t, J = 7.5, 3H, CH 3 ), 1.62 (sx, J = 7.5, 2H, CH 2 CH 3 ), 2.87 (s, 1H, OH), (m, 2H, OCH 2 CH 2 CH 3 ), 3.59 (dd, J = 11.7, 4.2, 1H, CH 2B OH), 3.68 (dd, J = 11.7, 8.3, 1H, CH 2A OH), 4.40 (dd, J = 8.3, 4.2, 1H, CHOCH 2 ), (m, 5H, H-aromatic), 13 C NMR (300 MHz; CDCl 3 ): δ 10.4 (CH 3 ), 22.9 (CH 2 CH 2 CH 3 ), 67.2 (OCH 2 CH 2 CH 3 ), 70.7 (OCH 2 OH), 82.8 (CHOH), (ortho), (para), (meta) (ipso); m/z (EI) 181 (M +, 5%), 165 (20), 150 (100), 122 (60), 108 (98), 91 (25), 79 (50). 2-iso-Propoxy-2-phenylethanol, IR ν max (CHCl 3 ) 3586, 3009, 2975, 1117, 1030 cm H NMR (300 MHz; CDCl 3 ): δ 1.16 (d, J = 6.0, 3H, CH 3 ), 1.23 (d, J = 6.0, 3H, CH 3 ), 3.13 (s, 1H, OH), (m, 3H, OCH(CH 3 ) 2, CH 2 OH), 4.56 (dd, J = 8.1, 3.9, CHOCH(CH 3 ) 2, (m, 5H, aromatics), 13 C NMR (300 MHz; CDCl 3 ): δ 21.0 (CH 3 ), 23.1 (CH 3 ), 67.1 (CH 2 OH), 69.1 (OCH(CH 3 ) 2 ), 79.9 (CHOCH(CH 3 ) 2 ), (ortho), (para), (meta), (ipso); m/z (EI) 181 (M +, 2%), 150 (40), 122 (20), 108 (100), 79 (50). 2-Butoxy-2-phenylethanol, IR ν max (CHCl 3 ) 3588, 2958, 2935, 1100, 1031 cm H NMR (300 MHz; CDCl 3 ): δ 0.95 (t, J = 7.5, 3H, CH 3 ), (m, 2H, CH 2 CH 3 ), (m, 2H, CH 2 CH 2 CH 3 ), 2.51 (s, 1H, OH), 3.37 (dt, J = 9.3, 6.3, OCH 2B ), 3.49 (dt, J = 9.3, 6.3, OCH 2A ), (m, 2H, CH 2 OH), 4.45 (dd, J = 8.4, 4.3, CHOCH 2 ), (m, 5H aromatics), 13 C NMR (300 MHz; CDCl 3 ): δ 13.9 (CH 3 ), 19.3 (CH 2 CH 3 ), 31.9 (CH 2 CH 2 CH 3 ), 67.4 (CH 2 OH), 68.9

2 (OCH 2 ), 82.8 (CHOCH 2 ), (ortho), (para), (meta), (ipso); m/z (EI) 195 (M +, 40%), 177 (50), 163 (70), 121 (100), 91 (30). 2-sec-Butoxy-2-phenylethanol (inseparable mixture of diastereomers), IR ν max (CHCl 3 ) 3586,2966, 2879, 1092, 1057 cm H NMR (300 MHz; CDCl 3 ): δ 0.82 (t, 3H, J = 7.5, CH 2 CH 3 ), 0.90 (t, 3H, J = 7.5, CH 3 ), 1.03 (d, 3H, J = 6.3, CHCH 3 ), 1.15 (d, 3H, J = 6.3, CHCH 3 ), (m, 4H, CH 2 CH 3, CH 2 CH 3 ), 2.36 (s, 1H, OH, OH), (m, 2H, OCH(CH 3 )CH 2 CH 3, OCH(CH 3 )CH 2 CH 3 ), (m, 4H, CH 2 OH, CH 2 OH), (m, 2H, PhCHOCH(CH 3 )CH 2 CH 3, PhCHOCH(CH 3 )CH 2 CH 3 ), (m, 10H, aromatics), 13 C NMR (300 MHz; CDCl 3 ): δ 9.3 (CH 3 ), 10.1 (CH 3 ), 18.6 (CHCH 3 ), 20.3 (CH 2 CH 3 ), 28.1 (CHCH 2 CH 3 ), 30.2 (CHCH 2 CH 3 ), 67.4 (CH 2 OCH(CH 3 )CH 2 CH 3 ), 67.5 (CH 2 OH), 73.9 (OCH(CH 3 )CH 2 CH 3 ), 75.1 (OCH(CH 3 )CH 2 CH 3 ), 79.5 (CHOCH(CH 3 )CH 2 CH 3 ), 80.6 (CHOH), (ortho), (ortho), (para), (para), (meta, meta), (ipso), (ipso); m/z (EI) 195 (M +, 10%), 177 (20), 163 (40), 121 (100), 107 (70), 79 (45). 2-tert-Butoxy-2-phenylethanol, mp: C. IR ν max (CHCl 3 ) 3586, 2977, 1369, 1060 cm H NMR (300 MHz; CDCl 3, TMSCl): δ 1.17 (s, 9H, 3 x CH 3 ), 2.01 (s, 1H, OH), 3.48 (dd, J = 11.4, 8.4, 1H, CH 2B OH), 3.52 (dd, J = 11.4, 4.2, 1H, CH 2A OH) 4.62 (dd, J = 8.4, 4.2, 1H, (CHOC(CH 3 ) 3 ), (m, 5H, H aromatic), 13 C NMR (300 MHz; CDCl 3 ): δ 28.8 (3 x CH 3 ), 67.9 (CH 2 ), 74.9 (OC(CH 3 ) 3 ), 75.1 (CH), (ortho), (para), (meta), (ipso); m/z (EI) 194 (M +, 3%), 163 (15), 121 (10), 107 (100), 79 (20). 1-Methoxybutan-2-ol (bold) and 2-Methoxybutan-1-ol (inseparable mixture of regioisomers), IR ν max (CHCl 3, of mixture) 3585, 2970, 2935, 1462, 1087 cm H NMR (300 MHz; CDCl 3 ): δ 0.88 (t, J = 7.5, 3H, CH 3 ), 0.93 (t, J = 7.5, 3H, CH 3 ), (m, 2H, CH 2 CH 3 ), (m, 2H, CH 2 CH 3 ), 2.15 (s, 1H, OH, OH), (m, 6H, CH 2 OCH 3, CHOH, CH 2 OH, CHOCH 3 ), 3.35 (s, 3H, OCH 3 ), 3.38 (s, 3H, OCH 3 ); 13 C NMR (300 MHz; CDCl 3 ): δ 9.5 (CH 3 ), 9.9 (CH 3 ), 22.9 (CH 2 CH 3 ), 26.0 (CH 2 CH 3 ), 57.0 (OCH 3 ), 59.0 (OCH 3 ), 63.5 (CH 2 OH), 71.6 (CHOH), 76.6 (CH 2 OCH 3 ), 82.8 (CHOCH 3 ); m/z (CI) 105 ([M+1] +, 100%), 87 (70), 73 (45). 1-Ethoxybutan-2-ol (bold) and 2-Ethoxybutan-1-ol (as an inseparable mixture of regioisomers), IR ν max (CHCl 3 ) 3583, 3009, 2976, 2880, 1107 cm H NMR (300 MHz; CDCl 3 ): δ 0.83 (t, J = 7.3, 3H, CHCH 2 CH 3 ), 0.88 (t, J = 7.2, 3H, CHCH 2 CH 3 ), 1.32 (t, J = 7.1, 3H, OCH 2 CH 3 ), 1.32 (t, J = 7.1, 3H, OCH 2 CH 3 ), (m, 2H, CHCH 2 CH 3 ), (m, 2H, CHCH 2 CH 3 ), 2.60 (s, 2H, OH, OH), (m, 2H, OCH 2B CH 3, CHOCH 2 CH 3 ), (m, 8H, OCH 2 CH 3, CH 2 OCH 2 CH 3, CHOH, CH 2 OH, OCH 2A CH 3 ), 13 C NMR (300 MHz; CDCl 3 ): δ 9.5 (CHCH 2 CH 3 ), 9.7 (CH 2 CH 3 ), 14.9 (OCH 2 CH 3 ), 15.4 (OCH 2 CH 3 ), 23.4 (CH 2 CH 3 ), 26.0 (CHCH 2 CH 3 ), 63.7 (OCH 2 CH 3 ), 64.7 (CH 2 OH), 66.6 (CH 2 OCH 2 CH 3 ), 71.5 (CHOH), 74.5 (OCH 2 CH 3 ), 81.1 (CH 2 OCH 2 CH 3 ); m/z (CI) 119 ([M+1] +, 100%), 101 (80), 73 (40). 1-iso-Propoxybutan-2-ol (bold) and 2-iso-Propoxybutan-1-ol (as an inseparable mixture of regioisomers), IR ν max (CHCl 3 ) 3580, 3009, 2978, 1128, 1071 cm H NMR (300 MHz; CDCl 3 ): δ 0.81 (t, J = 7.4, 3H, CH 2 CH 3 ), 0.86 (t, J = 7.5, 3H, CH 2 CH 3 ), 1.06 (t, J = 6.0, 6H, OCH(CH 3 ) 2 ), 1.06 (t, J = 6.0, 6H, OCH(CH 3 ) 2 ), (m, 4H, CH 2 CH 3 and CH 2 CH 3 ), 2.74 (s, 2H, OH, OH), (m, 8H, CH 2 OCH(CH 3 ) 2, OCH(CH 3 ) 2, CHOH, OCH(CH 3 ) 2, CH 2 OH, OCH(CH 2 ) 2 ), 13 C NMR (300 MHz; CDCl 3 ): δ 9.6 (CH 2 CH 3 ), 9.7 (CH 2 CH 3 ), 21.8 (CH(CH 3 )), 21.9 (CH(CH 3 )), 22.5 (CH(CH 3 )), 22.7 (CH(CH 3 )), 24.2 (CH 2 CH 3 ), 25.9 (CH 2 CH 3 ), 64.0 (CH 2 OH), 70.0 (CHOH), 71.6 (OCH(CH 3 ), 71.8 (CH(CH 3 ) 2 ), 72.0 (CH 2 OCH(CH 3 ) 2 ), 72.5 (OCH(CH 2 ) 2 ); m/z (CI) 132 ([M] +, 80%), 115 (20), 73 (100).

3 2-Methoxycyclohexanol, IR ν max (CHCl 3 ) 3566, 2920, 2829, 1120, 1080 cm H NMR (300 MHz; CDCl 3 ) δ 1.12 (m, 1H, H6 B ), (m, 3H, H3 B, H4 B, H5 B ), (m, 1H, 5 A ), (m, 1H, H4 A ), (m, 1H, H6 A ), (m, 1H, H3 A ), 2.92 (ddd, J = 10.5, 8.7, 4.5, 1H. CHOCH 3 ), 2.99 (s, 1H, OH), 3.38 (s, 3H, OCH 3 ), (m, 1H, CHOH), 13 C NMR (300 MHz; CDCl 3 ): δ 23.8 (C5), 23.9 (C4), 28.2 (C6), 32.0 (C3), 56.1 (OCH3), 73.4 (CHOH), 84.8 (CHOCH3); m/z (EI) 131 (M +, 20%), 113 (15), 98 (25), 84 (35), 71 (100). 2-Ethoxycyclohexanol, IR ν max (CHCl 3 ) 3579, 2970, 1451, 1090 cm H NMR (300 MHz; CDCl 3 ): δ 1.17 (t, J = 7.2, 3H, CH 3 ), (m, 4H, H3 B, H4 B, H5 B, H6 B ), (m, 2H, H4 A, H5 A ), (m, 2H, H3 A, H6 A ), 2.81 (s, 1H, OH), 2.97 (ddd, J = 10.5, 8.7, 4.5, 1H, CHOCH 2 CH 3 ), (m, 2H, HOCH, OCH 2B ), 4.12 (dq, J = 7.2, 0.9, 1H, OCH 2A ), 13 C NMR (300 MHz; CDCl 3 ): δ 15.6 (CH 3 ), 23.9 (C4 or C5), 24.2 (C4 or C5), 29.1 (C3 or C6), 31.9 (C3 or C6), 64.0 (OCH 2 CH 3 ), 71.6 (C1), 83.4 (C2); m/z (EI) 145 (M +, 20%), 127 (100), 85 (25), 81 (35), 57 (20). 2-Propoxycyclohexanol, IR ν max (CHCl 3 ) 3578, 2876, 1452, 1099, 1076 cm H NMR (300 MHz; CDCl 3 ): δ 0.84 (t, J = 7.1, 3H, CH 3 ), (m, 1H, H 3B, H 4B, H 5B, H 6B ), 1.50 (br sx, J = 7.0, 2H, CH 2 CH 3 ), (m, 2H, H 4A, H 5A ), (m, 2H, H 3A, H 6A ), 2.80 (s, OH), 2.92 (ddd, J = 10.5, 8.8, 4.3, 1H, CHOCH 2 CH 2 CH 3 ), 3.35 (dt, J = 9.3, 6.7, 1H, OCH 2B ), (m, 1H, CHOH), 3.39 (dt, J = 9.3, 6.7, 1H, OCH 2A ); 13 C NMR (300 MHz; CDCl 3 ): δ 10.4 (CH 3 ), 23.2 (CH 2 CH 3 ), 23.8 (C5), 24.1 (C4), 29.0 (C6), 31.9 (C3), 70.3 (OCH 2 ), 73.6 (CHOH), 83.4 (CHOCH 2 ); m/z (EI) 181 (M +, 2%), 159 (50), 141 (100), 99 (50), 81 (50). 2-iso-Propoxycyclohexanol, IR ν max (CHCl 3 ) 3455, 2853, 1454, 1134, 1039 cm H NMR (300 MHz; CDCl 3 ): δ 1.08 (d, J = 6.1, 3H, CH 3 ), 1.12 (d, J = 6.1, 3H, CH 3 ), (m, 2H, H 5B, H 6B ), (m, 4H, H 3B, H 4A, H 4B, H 5A ), (m, 1H, H 6A ), (m, 1H, H 3A ), 2.66 (s, 1H, OH), (m, 1H, CHOCH(CH 3 ) 2 ), (m, 1H, CHOH), 3.67 (septet, J = 6.1, 1H, CH(CH 3 ) 2 ). 13 C NMR (300 MHz; CDCl 3 ): δ 22.1 (CH 3 ), 23.7 (CH 3 ), 23.9 (C4 or C5), 24.3 (C4 or C5), 30.2 (C3 or C6), 31.9 (C3 or C6), 69.4 (CH(CH 3 ) 2 ), 73.6 (CHOH), 81.2 (CHOCH); m/z (EI) 159 (M +, 95%), 143 (100). 2-Butoxycyclohexanol, IR ν max (CHCl 3 ) 3579, 2976, 2932, 1080, 1093 cm H NMR (300 MHz; CDCl 3 ): δ 0.86 (t, J = 6.9, 3H, CH 3 ), (m, 1H, H 6B ), (m, 3H, H 3B, H 4B, H 5B ), (m, 2H, CH 2 CH 3 ), (m, 2H, OCH 2 CH 2 ), (m, 1H, H 5A ), (m, 1H, H 4A ), (m, 1H, H 6A ), (m, 1H, H 3A ), 2.62 (s, 1H, OH), 2.93 (ddd, J = 10.5, 8.7, 4.5, 1H, CHOCH 2 ), 3.22 (dt, J = 9.2, 6.6, 1H, OCH 2B ), (m, 1H, CHOH), 3.51 (dt, J = 9.2, 6.6, 1H, OCH 2A ). 13 C NMR (300 MHz; CDCl 3 ): δ 13.8 (CH 3 ), 19.3 (CH 2 CH 3 ), 23.9 (C5), 24.2 (C4), 29.1 (C6), 31.9 (C3), 32.2 (CH 2 CH 2 CH 3 ), 68.4 (OCH 2 ), 73.8 (CHOH), 83.6 (CHOCH 2 ); m/z (EI) 173 (M + 40%), 155 (100), 133 (10), 99 (20), 81 (30), 57 (25). 2-sec-Butoxycyclohexanol (inseparable mixture of diastereomers), IR ν max (CHCl 3 ) 3582, 2970, 2931, 1077, 1070 cm H NMR (300 MHz; CDCl 3 ): δ 0.86 (t, J = 7.4, 3H, CH 2 CH 3 ), 0.87 (t, J = 7.4, 3H, CH 2 CH 3 ), 1.08 (t, J = 2.7, OCHCH 3 ), 1.10 (t, J = 2.7, 3H, OCHCH 3 ), (m, 8H, CH 2B CH 3, CH 2B -3, CH 2B -4, CH 2B -6, CH 2B CH 3, CH 2B -3, CH 2B -4, CH 2B -6), (m, 8H, CH 2A CH 3, CH 2A -4, CH 2-5, CH 2A CH 3, CH 2A -4, CH 2-5), (m, 4H, CH 2A -3, CH 2A -6, CH 2A -3, CH 2A -6), 2.77 (s, 1H, OH, OH), (m, 2H, CHOCHCH 3, CHOCHCH 3 ), (m, 4H, CHOH, CHCH3, CHOH, CHCH3); 13 C NMR (300 MHz; CDCl 3 ): δ 9.8 (CH 2 CH 3 ), 10.2 (CH 2 CH 3 ), 19.8 (CHCH 3 ), 21.0 (CHCH 3 ), 23.9 (CH 2 CH 3 ), 24.7 (CH 2 CH 3 ), 29.3 (C5), 29.9 (C5), 30.3 (C4, C4), 30.7 (C6, C6), 31.9 (C3, C3), 73.6 (CHCH 3 ), 74.0 (CHCH 3 ),

4 74.3 (C1), 75.4 (C1), 80.9 (C2), 82.2 (C2). m/z (EI) 173 (M +, 90%), 155 (40), 177 (45), 99 (70), 81 (90). 2-tert-Butoxycyclohexanol, mp C. IR ν max (CHCl 3 ) 3488, 2978, 2939, 1193, 1066 cm -1 ; 1 H NMR (300 MHz; CDCl 3 ): δ 1.22 (s, 9H, CH 3 ), (m, 4H, H 3B, H 4B, H 5B, H 6B ), (m, 2H, H 4A, H 5A ), (m, 1H, H 6A ), (m, 1H, H 3A ), 2.51 (s, 1H, OH), (m, 1H, CHOC(CH 3 ) 3 ), (m, 1H, CHOH); 13 C NMR (300 MHz; CDCl 3 ): δ 24.2 (C5), 24.7 (C4), 29.1 (3 x CH 3 ), 32.1 (C6), 33.4 (C3), 73.9 (CHOH), 74.0 (C(CH 3 ) 3 ), 76.5 (CHOC(CH 3 ) 3 ); m/z (CI) 173 (M +, 10%), 155 (10), 117 (20), 99 (100), 81 (30). 2-Ethoxycyclododecanol, mp C. IR ν max (CHCl 3 ) 3562, 2933, 2866, 1446, 1098 cm H NMR (300 MHz; CDCl 3 ): δ 1.19 (t, J = 6.9, 3H, CH 3 ), (m, 16H, 8 x CH 2 ), (m, 4H, CH 2 CHOH, CH 2 CHOCH 2 CH 3 ), 2.42 (s, 1H, OH), 3.40 (dq, J = 9.3, 7.4, 1H, OCH 2B CH 3 ), (m, 2H, HCOH, OCH 2A CH 3 ), 13 C NMR (300 MHz; CDCl 3 ): δ 15.6 (CH 2 CH 3 ), 19.6, 22.2, (2C), 22.80, 23.2, 24.6, 25.0, 25.9, 29.3 (10 x CH 2, C3-C12), 64.8 (OCH 2 CH 3 ), 69.5 (CHOH), 80.5 (CHOCH 2 CH 3 ). m/z (EI) 229 (M +, 2%), 227 (20), 199 (20), 183 (20), 55 (100). 2-Butoxycyclododecanol, mp C. IR ν max (CHCl 3 ) 3557, 3015, 1233, 789, 711 cm H NMR (300 MHz; CDCl 3 ): δ 0.90 (t, J = 7.4, 3H, CH 2 CH 3 ), (m, 24H, 10CH 2, OCH 2 CH 2 CH 2 CH 3 ), 2.65 (s, 1H, OH), (m, 1H, CHO(CH 2 ) 3 CH 3 ), 3.31 (dt, J = 9.3, 6.5 (OCH 2B (CH 2 ) 2 CH 3 ), 3.64 (dt, J = 9.3, 6.5 (OCH 2A (CH 2 ) 2 CH 3 ), 3.70 (dt, J = 5.3, 2.4, CHOH), 3 C NMR (300 MHz; CDCl 3 ): δ 13.9 (CH 3 ), 19.4, 19.5, 22.2, 22.8 (3C), 23.1, 24.7, 25.1, 25.7, 29.3, 32.2 (12C, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, OCH 2 CH 2 CH 2 CH 3 ), 69.2 (OCH 2 ), 69.6 (CHOH), 80.6 (CHOCH 2 (CH 2 ) 2 CH 3 ); m/z (CI) 257 ([M+1] +, 45%), 239 (100), 183 (50), 165 (25). 1-Allyoxy-3-ethoxy-propan-2-ol, IR ν max (CHCl 3 ) 3578, 2975, 2881, 1647, 1097 cm H NMR (300 MHz; CDCl 3 ): δ 1.13 (t, J = 7.1, 3H, CH 3 ), 2.78 (s, 1H, OH), (m, 6H, OCH 2 CHOH, OCH 2 CH 3, CH 2 OCH 2 CH 3 ), (m, 1H, CHOH), 3.94 (dt, J = 5.6, 1.5, 2H, CH 2 =CHCH 2 ), 5.10 (app dq, J = 10.5, 1.5, 1H, HC=CH 2B ), 5.20 (app dq, J = 17.3, 1.5, HC=CH 2A ), 5.83 (ddt, J = 17.3, 10.5, 5.6, 1H, HC=CH 2 ); 13 C NMR (300 MHz; CDCl 3 ): δ 15.0 (CH 3 ), 66.7 (OCH 2 CH 3 ), 69.3 (CHOH), 71.3 (CH 2 OCH 2 CH 3 or OCH 2 CHOH), 71.6 (OCH 2 CHOH or CH 2 OCH 2 CH 3 ), 72.1 (HC=CH 2 CH 2 ), (HC=CH 2 ), (HC=CH 2 ); m/z (EI) 161 (M + 40%), 103 (35), 87 (45), 71 (35), 59 (100). 1-tert-Butoxy-3-ethoxy-propan-2-ol, IR ν max (CHCl 3 ) 3576, 2971, 1366, 1191, 1082 cm H NMR (300 MHz; CDCl 3 ): δ 1.16 (s, 9H, 3 x CH 3 ), 1.18 (t, J = 6.9, 3H, CH 2 CH 3 ), 2.40 (s, 1H, OH), (m, 7H, CHOH, OCH 2 CH 3, C(CH 3 ) 3 OCH 2, CH 2 OCH 2 CH 3 ); 13 C NMR (300 MHz; CDCl 3 ): δ 15.1 (OCH 2 CH 3 ), 27.5 (3 x CH 3 ), 62.9 (OCH 2 CH 3 ), 66.8 (C(CH 3 ) 3 OCH 2 ), 69.9 (CHOH), 71.7 (CH 2 OCH 2 CH 3 ), 78.2 (C(CH 3 ) 3 ); m/z (EI) 177 (M +, 40%), 121 (100), 103 (15), 57 (25). 1-Ethoxy-3-phenoxy-propan-2-ol, IR ν max (CHCl 3 ) 3586, 2979, 1495, 1120 cm H NMR (300 MHz; CDCl 3 ): δ 1.21 (t, J = 6.9, 3H, CH 3 ), 3.07 (br s, OH), (m, 4H, OCH 2 CH 3, CH 2 OCH 2 CH 3 ), (m, 2H, CHOCH 2 ), (m, 1H, CHOH), (m, 3H, Ho,p-aromatic), (m, 2H, Hm-aromatic); 13 C NMR (300 MHz; CDCl 3 ): δ 15.0 (OCH 2 CH 3 ), 66.9 (OCH 2 CH 3 ), 68.9 (CH 2 OCH 2 CH 3 ), 69.0 (CH), (Ph-OCH 2 ), (ortho),

5 120.9 (para), (meta), (ipso); m/z (EI) 196 (M +, 100%), 195 (30), 133 (35), 94 (70), 77 (45), 59 (100), 51 (30). 1-Ethoxy-3-(4-oxiranylmethoxy-butoxy)-propan-2-ol, IR ν max (CHCl 3 ) 3577, 2916, 1252, 1081, 909 cm H NMR (300 MHz; CDCl 3 ): δ 1.16 (t, J = 6.9, 3H, CH 3 ), (m, 4H, OCH 2 CH 2 CH 2 CH 2 O), 2.40 (br s, OH), 2.56 (dd, J = 5.0, 2.6, 1H, oxirane CH 2B OCHCH 2 ), 2.74 (t, J = 5.0, 1H, oxirane CH 2A OCHCH 2 ), (m, 1H, oxirane CH 2 OCHCH 2 ), (m, 12H, OCH 2 CH 3, CH 2 OCH 2 CH 3, OCH 2 CHOH, CH 2 CH 2 OCH 2 x 2, CHCH 2 OCH 2 ), (m, 1H, CHOH), 13 C NMR (300 MHz; CDCl 3 ): δ 14.7 (CH 3 ), 25.9 (CH 2 CH 2 ), 26.0 (CH 2 CH 2 ), 43.8 (CHOCH 2 oxirane), 50.5 (CHOCH 2 oxirane), 66.4 (OCH 2 CH 3 ), 69.0 (CHOH), (OCH 2 ), (OCH 2 ), 71.0 (OCH 2 ), 71.5 (OCH 2 ), 71.7 (OCH 2 ); m/z (EI) 249 ([M+1] +, 10%), 175 (10), 129 (100), 103 (35). 2-Ethoxy-3-[4-(2-ethoxy-3-hydroxy-propoxy)-butoxy]-propan-1-ol, IR ν max (CHCl 3 ) 3577, 2901, 1243, 1143, 1129 cm H NMR (300 MHz; CDCl 3 ): δ 1.13 (t, J = 6.9, 6H, 2 x CH 3 ), (m, 4H, 2 x CH 2 ), 2.78 (s, 2H, 2 x OH), (m, 16H, 2 x OCH 2 CH 3, 2 x CH 2 OCH 2 CH 3, 2 x CH 2 OCH 2 CHOH, 2 x CH 2 OCH 2 CHOH), 3.90 (m, 2H, 2 x CHOH), 13 C NMR (300 MHz; CDCl 3 ): δ 15.0 (2 x CH 3 ), 26.1 (OCH 2 CH 2 CH 2 CH 2 O), 66.7 (2 x OCH 2 CH 3 ), 69.3 (2 x CHOH), 71.1 (2 x OCH 2 ), 71.6 (2 x OCH 2 ), 71.9 (2 x OCH 2 ); m/z (EI) 294 (M +, 40%), 175 (100), 147 (15), 115 (30), 59 (40).

6 OCH 2 CH 3 OH

7 OH OCH 2 CH 2 CH 3

8 O OH OCH 2 CH 3

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Information NbCl 3 -catalyzed [2+2+2] intermolecular cycloaddition of alkynes and alkenes to 1,3-cyclohexadiene derivatives Yasushi Obora,* Keisuke Takeshita and Yasutaka Ishii*

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information for AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds Qiuping Ding 1, Dan Wang 1, Puying Luo* 2, Meiling Liu 1, Shouzhi Pu* 3 and

Διαβάστε περισσότερα

The Free Internet Journal for Organic Chemistry

The Free Internet Journal for Organic Chemistry The Free Internet Journal for Organic Chemistry Paper Archive for Organic Chemistry Arkivoc 2018, part iii, S1-S6 Synthesis of dihydropyranones and dihydropyrano[2,3- d][1,3]dioxine-diones by cyclization

Διαβάστε περισσότερα

Hiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl

Hiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl Hiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl Philippe Pierrat, Philippe Gros* and Yves Fort Synthèse Organométallique

Διαβάστε περισσότερα

Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic acids with the assistance of isocyanide

Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic acids with the assistance of isocyanide Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic

Διαβάστε περισσότερα

Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone.

Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone. Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone. Won-Suk Kim, Hyung-Jin Kim and Cheon-Gyu Cho Department of Chemistry, Hanyang University, Seoul 133-791, Korea Experimental Section

Διαβάστε περισσότερα

Site-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran

Site-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran 1 Site-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran Munawar Hussain, a Rasheed Ahmad Khera, a Nguyen Thai Hung, a Peter Langer* a,b a Institut für Chemie, Universität Rostock,

Διαβάστε περισσότερα

A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes

A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes

Διαβάστε περισσότερα

Free Radical Initiated Coupling Reaction of Alcohols and. Alkynes: not C-O but C-C Bond Formation. Context. General information 2. Typical procedure 2

Free Radical Initiated Coupling Reaction of Alcohols and. Alkynes: not C-O but C-C Bond Formation. Context. General information 2. Typical procedure 2 Free Radical Initiated Coupling Reaction of Alcohols and Alkynes: not C-O but C-C Bond Formation Zhongquan Liu,* Liang Sun, Jianguo Wang, Jie Han, Yankai Zhao, Bo Zhou Institute of Organic Chemistry, Gannan

Διαβάστε περισσότερα

Available online at

Available online at J. Serb. Chem. Soc. 76 (12) S1 S5 (2011) Supplementary material SUPPLEMENTARY MATERIAL TO Synthesis of quinoline-attached furan-2(3h)-ones having anti-inflammatory and antibacterial properties with reduced

Διαβάστε περισσότερα

Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3

Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3 Supporting Information Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3 Shohei Shimokawa, Yuhsuke Kawagoe, Katsuhiko Moriyama, Hideo Togo* Graduate

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information Montmorillonite KSF-Catalyzed One-pot, Three-component, Aza-Diels- Alder Reactions of Methylenecyclopropanes With Arylaldehydes and Aromatic Amines Li-Xiong Shao and Min Shi* General

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information Lewis acid catalyzed ring-opening reactions of methylenecyclopropanes with diphenylphosphine oxide in the presence of sulfur or selenium Min Shi,* Min Jiang and Le-Ping Liu State

Διαβάστε περισσότερα

Copper-Catalyzed Oxidative Dehydrogenative N-N Bond. Formation for the Synthesis of N,N -Diarylindazol-3-ones

Copper-Catalyzed Oxidative Dehydrogenative N-N Bond. Formation for the Synthesis of N,N -Diarylindazol-3-ones Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2016 Supporting information Copper-Catalyzed Oxidative Dehydrogenative - Bond Formation

Διαβάστε περισσότερα

Supporting Information One-Pot Approach to Chiral Chromenes via Enantioselective Organocatalytic Domino Oxa-Michael-Aldol Reaction

Supporting Information One-Pot Approach to Chiral Chromenes via Enantioselective Organocatalytic Domino Oxa-Michael-Aldol Reaction Supporting Information ne-pot Approach to Chiral Chromenes via Enantioselective rganocatalytic Domino xa-michael-aldol Reaction Hao Li, Jian Wang, Timiyin E-Nunu, Liansuo Zu, Wei Jiang, Shaohua Wei, *

Διαβάστε περισσότερα

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Information Unprecedented Carbon-Carbon Bond Cleavage in Nucleophilic Aziridine Ring Opening Reaction, Efficient Ring Transformation of Aziridines to Imidazolidin-4-ones Jin-Yuan

Διαβάστε περισσότερα

Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006

Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006 Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 A new route to enantiopure b-aryl-substituted b-amino acids and 4-aryl-substituted b-lactams through lipase-catalyzed

Διαβάστε περισσότερα

SUPPORTING INFORMATION. 1. General... S1. 2. General procedure for the synthesis of compounds 3 and 4 in the absence of AgOAc...

SUPPORTING INFORMATION. 1. General... S1. 2. General procedure for the synthesis of compounds 3 and 4 in the absence of AgOAc... SUPPORTING INFORMATION Table of contents 1. General.... S1 2. General procedure for the synthesis of compounds 3 and 4 in the absence of AgOAc... S2 3. General procedure for the synthesis of compounds

Διαβάστε περισσότερα

Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes

Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes Supporting Information for Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes Changkun Li and Jianbo Wang* Beijing National Laboratory

Διαβάστε περισσότερα

Supporting Information. Asymmetric Binary-acid Catalysis with Chiral. Phosphoric Acid and MgF 2 : Catalytic

Supporting Information. Asymmetric Binary-acid Catalysis with Chiral. Phosphoric Acid and MgF 2 : Catalytic Supporting Information Asymmetric Binary-acid Catalysis with Chiral Phosphoric Acid and MgF 2 : Catalytic Enantioselective Friedel-Crafts Reactions of β,γ- Unsaturated-α-Ketoesters Jian Lv, Xin Li, Long

Διαβάστε περισσότερα

Phosphorus Oxychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions

Phosphorus Oxychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions Supplementary Information for Phosphorus xychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions u Chen,* a,b Xunfu Xu, a Liu Liu, a Guo Tang,* a

Διαβάστε περισσότερα

SUPPLEMENTARY DATA. Waste-to-useful: Biowaste-derived heterogeneous catalyst for a green and sustainable Henry reaction

SUPPLEMENTARY DATA. Waste-to-useful: Biowaste-derived heterogeneous catalyst for a green and sustainable Henry reaction Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 209 SUPPLEMENTARY DATA Waste-to-useful:

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2014 A Family of Click Nucleosides for Metal-Mediated Base Pairing: Unravelling the Principles of Highly Stabilizing Metal-Mediated

Διαβάστε περισσότερα

Synthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and D-homoandrostane. Tandem Click reaction/cu-catalyzed D-homo rearrangement

Synthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and D-homoandrostane. Tandem Click reaction/cu-catalyzed D-homo rearrangement Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information Synthesis of novel 1,2,3-triazolyl derivatives of

Διαβάστε περισσότερα

Mandelamide-Zinc Catalyzed Alkyne Addition to Heteroaromatic Aldehydes

Mandelamide-Zinc Catalyzed Alkyne Addition to Heteroaromatic Aldehydes 1 Mandelamide-Zinc Catalyzed Alkyne Addition to Heteroaromatic Aldehydes Gonzalo Blay, Isabel Fernández, Alícia Marco-Aleixandre, and José R. Pedro Departament de Química Orgànica, Facultat de Química,

Διαβάστε περισσότερα

Electronic Supplementary Information. Carbon dioxide as a reversible amine-protecting

Electronic Supplementary Information. Carbon dioxide as a reversible amine-protecting Electronic Supplementary Information Carbon dioxide as a reversible amine-protecting agent in selective Michael additions and acylations Annelies Peeters, Rob Ameloot and Dirk E. De Vos * Centre for Surface

Διαβάστε περισσότερα

Highly enantioselective cascade synthesis of spiropyrazolones. Supporting Information. NMR spectra and HPLC traces

Highly enantioselective cascade synthesis of spiropyrazolones. Supporting Information. NMR spectra and HPLC traces Highly enantioselective cascade synthesis of spiropyrazolones Alex Zea a, Andrea-Nekane R. Alba a, Andrea Mazzanti b, Albert Moyano a and Ramon Rios a,c * Supporting Information NMR spectra and HPLC traces

Διαβάστε περισσότερα

Room Temperature Highly Diastereoselective Zn-Mediated. Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled

Room Temperature Highly Diastereoselective Zn-Mediated. Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled Supporting Information for: Room Temperature Highly Diastereoselective Zn-Mediated Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled Stereoselectivity Reversal

Διαβάστε περισσότερα

Supporting Information. Experimental section

Supporting Information. Experimental section Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Experimental section General. Proton nuclear magnetic resonance ( 1

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information Ceric Ammonium Nitrate (CAN) catalyzed efficient one-pot three component aza-diels-alder reactions for a facile synthesis of tetrahydropyranoquinoline derivatives Ravinder Goud Puligoundla

Διαβάστε περισσότερα

SUPPLEMENTARY MATERIAL

SUPPLEMENTARY MATERIAL 10.1071/CH16014_AC The Authors 2016 Australian Journal of Chemistry 2016, 69(9), 1049-1053 SUPPLEMENTARY MATERIAL A Green Approach for the Synthesis of Novel 7,11-Dihydro-6H-chromeno[3,4- e]isoxazolo[5,4-b]pyridin-6-one

Διαβάστε περισσότερα

Metal-free Oxidative Coupling of Amines with Sodium Sulfinates: A Mild Access to Sulfonamides

Metal-free Oxidative Coupling of Amines with Sodium Sulfinates: A Mild Access to Sulfonamides Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting information for Metal-free Oxidative Coupling of Amines with Sodium Sulfinates:

Διαβάστε περισσότερα

Divergent synthesis of various iminocyclitols from D-ribose

Divergent synthesis of various iminocyclitols from D-ribose Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 205 Divergent synthesis of various iminocyclitols from D-ribose Ramu Petakamsetty,

Διαβάστε περισσότερα

Supporting Information. Synthesis and in vitro pharmacological evaluation of N-[(1-benzyl-1,2,3-triazol-4-

Supporting Information. Synthesis and in vitro pharmacological evaluation of N-[(1-benzyl-1,2,3-triazol-4- Supporting Information Synthesis and in vitro pharmacological evaluation of N-[(1-benzyl-1,2,3-triazol-4- yl)methyl]-carboxamides on D-secoestrone scaffolds Johanna Szabó a, Ildikó Bacsa a, János Wölfling

Διαβάστε περισσότερα

Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%.

Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%. Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%. S1 Supplementary Figure S2. Single X-ray structure 5a at probability ellipsoids of 20%. S2 H 15 Ph Ac Ac I AcH Ph Ac

Διαβάστε περισσότερα

Synthesis of eunicellane-type bicycles embedding a 1,3- cyclohexadiene moiety

Synthesis of eunicellane-type bicycles embedding a 1,3- cyclohexadiene moiety Supporting Information for Synthesis of eunicellane-type bicycles embedding a 1,3- cyclohexadiene moiety Alex Frichert, 1 Peter G. Jones, 2 and Thomas Lindel*,,1 Address: 1 Institute of Organic Chemistry,

Διαβάστε περισσότερα

Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst- and solvent-free thermal multicomponent domino reaction

Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst- and solvent-free thermal multicomponent domino reaction Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 SUPPRTIG IFRMATI Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst-

Διαβάστε περισσότερα

Answers and Spectroscopic Assignments Copyright 2012

Answers and Spectroscopic Assignments Copyright 2012 Organic Structure Elucidation - A Workbook of Unknowns www.nd.edu/~smithgrp/structure/workbook.html Answers and Spectroscopic Assignments Carleton G. Collins, Department of Chemistry and Biochemistry,

Διαβάστε περισσότερα

Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006

Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006 Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 1 A Facile Way to Synthesize 2H-Chromenes: Reconsideration of the Reaction Mechanism between Salicylic Aldehyde and

Διαβάστε περισσότερα

D-Glucosamine-derived copper catalyst for Ullmann-type C- N coupling reaction: theoretical and experimental study

D-Glucosamine-derived copper catalyst for Ullmann-type C- N coupling reaction: theoretical and experimental study Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 D-Glucosamine-derived copper catalyst for Ullmann-type C- N coupling reaction: theoretical

Διαβάστε περισσότερα

Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process

Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process Jincan Zhao 1, Hong Fang 1, Jianlin Han* 1,2 and Yi Pan* 1

Διαβάστε περισσότερα

Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent

Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent Supplementary information for the paper Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent Yang Xue, Ling-Po Li, Yan-Hong He * & Zhi Guan * School of Chemistry and Chemical Engineering,

Διαβάστε περισσότερα

Supporting information

Supporting information Supporting information Spectroscopic data of compounds 1a-f Benzyl bromide (1a) Yield: 81%. Colorless oil. b.p. 79-82 o C/15 mmhg (Lit. 83.5 84 o C/13 mmhg). 1 1 H NMR (CDCl 3 ): δ 4.45 (2H, s, PhCH 2

Διαβάστε περισσότερα

Available online at shd.org.rs/jscs/

Available online at shd.org.rs/jscs/ J. Serb. Chem. Soc. 78 (12) S131 S136 (2013) Supplementary material SUPPLEMENTARY MATERIAL TO New 9-aminoacridine derivatives as inhibitors of botulinum neurotoxins and P. falciparum malaria MIKLOŠ TOT

Διαβάστε περισσότερα

Pyrrolo[2,3-d:5,4-d']bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-ring Bithiophenes

Pyrrolo[2,3-d:5,4-d']bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-ring Bithiophenes SUPPORTING INFORMATION Pyrrolo[2,3-d:5,4-d']bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-ring Bithiophenes Eric J. Uzelac, Casey B. McCausland, and Seth C. Rasmussen*

Διαβάστε περισσότερα

First DMAP-mediated direct conversion of Morita Baylis. Hillman alcohols into γ-ketoallylphosphonates: Synthesis of

First DMAP-mediated direct conversion of Morita Baylis. Hillman alcohols into γ-ketoallylphosphonates: Synthesis of Supporting Information File 1 for First DMAP-mediated direct conversion of Morita Baylis Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates Marwa Ayadi 1,2, Haitham Elleuch

Διαβάστε περισσότερα

Fischer Indole Synthesis in Low Melting Mixtures

Fischer Indole Synthesis in Low Melting Mixtures Fischer Indole Synthesis in Low Melting Mixtures Sangram Gore, a,b Sundarababu Baskaran* a and Burkhard König* b Supporting Information Table of Contents: General Information General Procedure for the

Διαβάστε περισσότερα

Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate

Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate upporting Information Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate Jing-Yu Wu, Zhi-Bin Luo, Li-Xin Dai and Xue-Long Hou* a tate Key Laboratory of Organometallic

Διαβάστε περισσότερα

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003 Supporting Information for Angew. Chem. Int. Ed. Z52857 Wiley-VC 2003 69451 Weinheim, Germany Palladium Catalyzed DYKAT of Vinyl Epoxide: Enantioselective Total Synthesis and Assignment of Configuration

Διαβάστε περισσότερα

Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006

Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006 Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 Silver-Catalyzed Asymmetric Synthesis of 2,3-Dihydrobenzofurans: A New Chiral Synthesis of Pterocarpans Leticia Jiménez-González, Sergio

Διαβάστε περισσότερα

New Cytotoxic Constituents from the Red Sea Soft Coral Nephthea sp.

New Cytotoxic Constituents from the Red Sea Soft Coral Nephthea sp. SUPPLEMENTARY MATERIAL New Cytotoxic Constituents from the Red Sea Soft Coral Nephthea sp. Mohamed-Elamir F. Hegazy a,*, Amira M. Gamal-Eldeen b, Tarik A. Mohamed a, Montaser A. Alhammady c, Abuzeid A.

Διαβάστε περισσότερα

Phenylpropanoids, Sesquiterpenoids and Flavonoids from Pimpinella tragium Vill. subsp. lithophila (Schischkin) Tutin

Phenylpropanoids, Sesquiterpenoids and Flavonoids from Pimpinella tragium Vill. subsp. lithophila (Schischkin) Tutin Supporting Information Rec. Nat. Prod. 10:2 (2016) 207-213 Phenylpropanoids, Sesquiterpenoids and Flavonoids from Pimpinella tragium Vill. subsp. lithophila (Schischkin) Tutin Hilal Özbek 1, Zühal Güvenalp

Διαβάστε περισσότερα

1011 Σύνθεση του 1,4-δι-tert-βουτυλοβενζολίου από tertβουτυλοβενζόλιο και tert-βουτυλο χλωρίδιο

1011 Σύνθεση του 1,4-δι-tert-βουτυλοβενζολίου από tertβουτυλοβενζόλιο και tert-βουτυλο χλωρίδιο 1011 Σύνθεση του 1,4-δι-tert-βουτυλοβενζολίου από tertβουτυλοβενζόλιο και tert-βουτυλο χλωρίδιο + Cl AlCl 3 C 10 H 14 (134.) C 4 H 9 Cl C 14 H (9.6) (133.3) (190.3) Ταξινόµηση Τύποι αντιδράσεων και τάξεις

Διαβάστε περισσότερα

First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin

First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin Takahiro Suzuki, a Kenji Usui, a Yoshiharu Miyake, a Michio Namikoshi, b and Masahisa Nakada a, * a Department of Chemistry, School of Science

Διαβάστε περισσότερα

Efficient Synthesis of Ureas by Direct Palladium-Catalyzed. Oxidative Carbonylation of Amines

Efficient Synthesis of Ureas by Direct Palladium-Catalyzed. Oxidative Carbonylation of Amines S1 Supporting Information for Efficient Synthesis of Ureas by Direct Palladium-Catalyzed Oxidative Carbonylation of Amines Bartolo Gabriele,*, Giuseppe Salerno, Raffaella Mancuso, and Mirco Costa Dipartimento

Διαβάστε περισσότερα

gem-dichloroalkenes for the Construction of 3-Arylchromones

gem-dichloroalkenes for the Construction of 3-Arylchromones Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Pd(OAc)2/S=PPh3 Accelerated Activation of gem-dichloroalkenes for the Construction of 3-Arylchromones

Διαβάστε περισσότερα

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information Silver or Cerium-Promoted Free Radical Cascade Difunctionalization

Διαβάστε περισσότερα

Sotto, 8; Perugia, Italia. Fax: ; Tel: ;

Sotto, 8; Perugia, Italia. Fax: ; Tel: ; ELECTRONIC SUPPORTING INFORMATION Ermal Ismalaj a, Giacomo Strappaveccia a, Eleonora Ballerini a, Fausto Elisei a, Oriana Piermatti a, Dmitri Gelman b, Luigi Vaccaro a a CEMIN - Dipartimento di Chi mica,

Διαβάστε περισσότερα

Kishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, and Xiao-Feng Wu*

Kishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, and Xiao-Feng Wu* Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 204 Kishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, and Xiao-Feng

Διαβάστε περισσότερα

Supporting information for

Supporting information for Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting information for Mesoporous silica KIT-6 supported superparamagnetic CuFe 2 O

Διαβάστε περισσότερα

Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information

Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans Liang Yun, Shi Tang, Xu-Dong Zhang, Li-Qiu Mao, Ye-Xiang Xie and Jin-Heng Li* Key Laboratory

Διαβάστε περισσότερα

SUPPORTING INFORMATION

SUPPORTING INFORMATION SUPPORTING INFORMATION Heronamides A C, new polyketide macrolactams from an Australian marine-derived Streptomyces sp. A biosynthetic case for synchronized tandem electrocyclization. Ritesh Raju, Andrew

Διαβάστε περισσότερα

9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer catalysts

9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer catalysts Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer

Διαβάστε περισσότερα

Asymmetric Synthesis of New Chiral β-amino Acid Derivatives by Mannich-type Reactions of Chiral N- Sulfinyl Imidates with N-Tosyl Aldimines

Asymmetric Synthesis of New Chiral β-amino Acid Derivatives by Mannich-type Reactions of Chiral N- Sulfinyl Imidates with N-Tosyl Aldimines Asymmetric Synthesis of New Chiral β-amino Acid Derivatives by Mannich-type Reactions of Chiral N- Sulfinyl Imidates with N-yl Aldimines Filip Colpaert, Sven Mangelinckx, and Norbert De Kimpe Department

Διαβάστε περισσότερα

Supporting Information. Experimental section

Supporting Information. Experimental section Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Experimental section General. Anhydrous solvents were transferred by

Διαβάστε περισσότερα

Iodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via double C(sp 2 )-H thiolation

Iodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via double C(sp 2 )-H thiolation Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Iodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information for Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction Chun-Huan Jiang, Xiantao Lei,

Διαβάστε περισσότερα

Modular Synthesis of Cyclic cis- and trans-1,2-diamine Derivatives

Modular Synthesis of Cyclic cis- and trans-1,2-diamine Derivatives Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 4 Modular Synthesis of Cyclic cis- and trans-,-diamine Derivatives Anna K. Weber,

Διαβάστε περισσότερα

Supporting Information for Fe-Catalyzed Reductive Coupling of Unactivated Alkenes with. β-nitroalkenes. Contents. 1. General Information S2

Supporting Information for Fe-Catalyzed Reductive Coupling of Unactivated Alkenes with. β-nitroalkenes. Contents. 1. General Information S2 Supporting Information for Fe-Catalyzed Reductive Coupling of Unactivated Alkenes with β-nitroalkenes Jing Zheng, Dahai Wang, and Sunliang Cui* College of Pharmaceutical Sciences, Zhejiang University,

Διαβάστε περισσότερα

Supporting information

Supporting information Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting information Copper-catalysed intramolecular O-arylation: a simple

Διαβάστε περισσότερα

SUPPORTING INFORMATION

SUPPORTING INFORMATION Eur. J. Org. Chem. 2006 WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 ISSN 1434 193X SUPPORTING INFORMATION Title: Sulfonamide Ligands Attained Through Opening of Saccharin Derivatives Author(s):

Διαβάστε περισσότερα

Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu , Japan

Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu , Japan Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Supplementary information Unprecedented formation of η 4 -(vinylketene)iron complexes from η 4

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information Wiley-VC 007 9 Weinheim, Germany ew ear Infrared Dyes and Fluorophores Based on Diketopyrrolopyrroles Dipl.-Chem. Georg M. Fischer, Dipl.-Chem. Andreas P. Ehlers, Prof. Dr. Andreas

Διαβάστε περισσότερα

Supporting Information. Synthesis and biological evaluation of nojirimycin- and

Supporting Information. Synthesis and biological evaluation of nojirimycin- and Supporting Information for Synthesis and biological evaluation of nojirimycin- and pyrrolidine-based trehalase inhibitors Davide Bini 1, Francesca Cardona 2, Matilde Forcella 1, Camilla Parmeggiani 2,3,

Διαβάστε περισσότερα

Rhodium-Catalyzed Oxidative Decarbonylative Heck-type Coupling of Aromatic Aldehydes with Terminal Alkenes

Rhodium-Catalyzed Oxidative Decarbonylative Heck-type Coupling of Aromatic Aldehydes with Terminal Alkenes Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information Rhodium-Catalyzed Oxidative Decarbonylative Heck-type

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information Copper/Silver Cocatalyzed Oxidative Coupling of Vinylarenes with ICH 2 CF 3 or ICH 2 CHF 2 Leading to β-cf 3 /CHF 2 -Substituted Ketones Niannian Yi, Hao Zhang, Chonghui Xu, Wei

Διαβάστε περισσότερα

Facile construction of the functionalized 4H-chromene via tandem. benzylation and cyclization. Jinmin Fan and Zhiyong Wang*

Facile construction of the functionalized 4H-chromene via tandem. benzylation and cyclization. Jinmin Fan and Zhiyong Wang* Facile construction of the functionalized 4H-chromene via tandem benzylation and cyclization Jinmin Fan and Zhiyong Wang* Hefei National Laboratory for Physical Science at Microscale, Joint- Lab of Green

Διαβάστε περισσότερα

Supporting information

Supporting information Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 204 Supporting information Palladium nanoparticles supported on triazine functionalised mesoporous

Διαβάστε περισσότερα

Fluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine Reagents. An Efficient Method for 1,3- Oxyfluorination and 1,3-Difluorination

Fluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine Reagents. An Efficient Method for 1,3- Oxyfluorination and 1,3-Difluorination Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2016 Supporting Information Fluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine

Διαβάστε περισσότερα

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for rganic Chemistry Frontiers. This journal is the Partner rganisations 2018 Palladium-catalyzed direct approach to α-cf 3 aryl ketones from arylboronic acids Bo

Διαβάστε περισσότερα

Eur. J. Org. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006 ISSN X SUPPORTING INFORMATION

Eur. J. Org. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006 ISSN X SUPPORTING INFORMATION Eur. J. rg. Chem. 2006 WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 ISSN 1434 193X SUPPRTING INFRMATIN Title: ne-pot Synthesis of xo Acid Derivatives by Rh I -Catalyzed Chelation-Assisted Hydroacylation

Διαβάστε περισσότερα

The N,S-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H. Carbonylation using Langlois Reagent as CO Source. Supporting Information.

The N,S-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H. Carbonylation using Langlois Reagent as CO Source. Supporting Information. Electronic upplementary Material (EI) for rganic & Biomolecular Chemistry. This journal is The Royal ociety of Chemistry 2018 The,-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H Carbonylation using

Διαβάστε περισσότερα

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information 1. General experimental methods (S2). 2. Table 1: Initial studies (S2-S4).

Διαβάστε περισσότερα

Palladium-Catalyzed Direct ortho-sulfonylation of. Azobenzenes with Arylsulfonyl Chlorides via C H. Table of Contents

Palladium-Catalyzed Direct ortho-sulfonylation of. Azobenzenes with Arylsulfonyl Chlorides via C H. Table of Contents Electronic upplementary Material (EI) for RC Advances. This journal is The Royal ociety of Chemistry 205 upporting Information Palladium-Catalyzed Direct ortho-ulfonylation of Azobenzenes with Arylsulfonyl

Διαβάστε περισσότερα

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Synthesis of 3-omosubstituted Pyrroles via Palladium- Catalyzed Intermolecular Oxidative Cyclization

Διαβάστε περισσότερα

Total synthesis and cytotoxicity of the marine. natural product malevamide D and a photoreactive

Total synthesis and cytotoxicity of the marine. natural product malevamide D and a photoreactive Supporting Information for Total synthesis and cytotoxicity of the marine natural product malevamide D and a photoreactive analog Werner Telle 1, Gerhard Kelter 2, Heinz-Herbert Fiebig 2, Peter G. Jones

Διαβάστε περισσότερα

Supplementary Data. Engineering, Nanjing University, Nanjing , P. R. China;

Supplementary Data. Engineering, Nanjing University, Nanjing , P. R. China; 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

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information Lewis Acid Mediated [2,3]-Sigmatropic Rearrangement of Allylic α-amino Amides. Jan Blid, Peter Brandt, Peter Somfai*, Department of Chemistry, rganic Chemistry, Royal Institute of

Διαβάστε περισσότερα

π-face DONOR PROPERTIES OF N-HETEROCYCLIC CARBENES MARCUS SÜßNER AND HERBERT PLENIO

π-face DONOR PROPERTIES OF N-HETEROCYCLIC CARBENES MARCUS SÜßNER AND HERBERT PLENIO π-face DR PRPERTIES F -ETERCYCLIC CARBEES MARCUS SÜßER AD ERBERT PLEI ARGAISCE CEMIE IM ZITL-ISTITUT DES FB CEMIE, TU DARMSTADT, PETERSESTR. 18, 64287 DARMSTADT, GERMAY E-MAIL: PLEI@TU-DARMSTADT.DE Cyclic

Διαβάστε περισσότερα

Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles

Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry SUPPRTIG IFRMATI Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles Anahit Pews-Davtyan and Matthias Beller* Leibniz-Institut

Διαβάστε περισσότερα

Electronic Supporting Information

Electronic Supporting Information Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information robing steric influences on electrophilic phosphonium

Διαβάστε περισσότερα

Supplementary Materials

Supplementary Materials Supplementary Materials Figure S1. Chemical structures of phloracetophenone intermediates (2a, 2c 2g). 2a 2c 2d 2e 2f 2g Figure S2. Chemical structures of geranylacetophenone analogues (3a, 3c, 3e g).

Διαβάστε περισσότερα

Synthesis of Imines from Amines in Aliphatic Alcohols on Pd/ZrO 2 Catalyst at Ambient Conditions

Synthesis of Imines from Amines in Aliphatic Alcohols on Pd/ZrO 2 Catalyst at Ambient Conditions This journal is The Royal Society of Chemistry 213 Synthesis of Imines from Amines in Aliphatic Alcohols on Pd/ZrO 2 Catalyst at Ambient Conditions Wenjing Cui, a Bao Zhaorigetu,* a Meilin Jia, a and Wulan

Διαβάστε περισσότερα

Supplementary Information

Supplementary Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 215 Supplementary Information Zinc monoglycerolate as a catalyst for the conversion of 1,3- and

Διαβάστε περισσότερα

Enantioselective Organocatalytic Michael Addition of Isorhodanines. to α, β-unsaturated Aldehydes

Enantioselective Organocatalytic Michael Addition of Isorhodanines. to α, β-unsaturated Aldehydes Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Enantioselective Organocatalytic Michael Addition of Isorhodanines to α,

Διαβάστε περισσότερα

Brønsted Acid-Catalyzed Hydroarylation of Activated. Olefins

Brønsted Acid-Catalyzed Hydroarylation of Activated. Olefins Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 204 Brønsted Acid-Catalyzed Hydroarylation of Activated Olefins Ivana Fleischer* and Jola Pospech

Διαβάστε περισσότερα

Zuxiao Zhang, Xiaojun Tang and William R. Dolbier, Jr.* Department of Chemistry, University of Florida, Gainesville, FL

Zuxiao Zhang, Xiaojun Tang and William R. Dolbier, Jr.* Department of Chemistry, University of Florida, Gainesville, FL Photoredox-Catalyzed Intramolecular Difluoromethylation of -Benzylacrylamides Coupled with a Dearomatizing Spirocyclization: Access to CF2H Containing 2- Azaspiro[4.5]deca-6,9-diene-3,8-diones. Zuxiao

Διαβάστε περισσότερα

Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008

Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 Palladium(0)-catalyzed direct cross-coupling reaction of allylic alcohols with aryland alkenylboronic acids Hirokazu Tsukamoto, Tomomi Uchiyama, Takamichi Suzuki and Yoshinori Kondo Graduate School of

Διαβάστε περισσότερα

Supplementary Information for

Supplementary Information for Supplementary Information for Organocatalytic Asymmetric Intramolecular [3+2] Cycloaddition: A Straightforward Approach to Access Multiply Substituted Hexahydrochromeno[4,3-b]pyrrolidine Derivatives in

Διαβάστε περισσότερα

Extended dissolution studies of cellulose in imidazolium based ionic liquids

Extended dissolution studies of cellulose in imidazolium based ionic liquids Electronic Supplementary Information Extended dissolution studies of cellulose in imidazolium based ionic liquids Jürgen Vitz, a,b Tina Erdmenger, a,b Claudia Haensch, a,b Stephanie Hornig # and Ulrich

Διαβάστε περισσότερα