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Electrophilic Monoiodination of Terminal Alkenes Supplementary PDF

41 Pages·2013·2.36 MB·English
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Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2013 Electrophilic Monoiodination of Terminal Alkenes Sergiy V. Yemets,a Tatyana E. Shubinab and Pavel A. Krasutsky*a a University of Minnesota, Natural Resources Research Institute, 5013 Miller Trunk Highway, Duluth, MN 55811, United States; E-mail: [email protected] b Computer-Chemie-Centrum and Interdisciplinary Center for Molecular Materials,University Erlangen-Nuremberg, Nägelsbachstr 25, Germany 91052 Supplementary Information 1. 1H and 13C NMR spectra……………………………………………………………………...2 2. Kinetic measurement data……………………………………………………………………21 3. Optimized geometries for all species…………………………………………………………34 1 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2013 1 13 1. H and C NMR spectra NMR spectra for all synthesized compounds (300 MHz 1H NMR and 75 MHz 13C NMR) were recorded using Varian Unity Inova 300. 1H and 13C NMR chemical shifts are referenced to tetramethylsilane as internal standard and reported in parts per million (ppm). 2 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry M This journal is © The Royal Society of Chemistry 2013 P P 0 0 566.0 8. 807.0 3 067.0 528.0 079.0 1 989.0 030.1 793.1 304.1 636.1 586.1 039.1 789.1 102.2 2 922.2 072.2 182.2 00 903.2 2. 123.2 243.2 753.2 773.2 393.2 s m 3 t 0 /3 0 161.3 1. Cl 771.3 0 D 361921..33 1.0 C 313.3 ), 943.3 8 ( ol 00 di 1. 8- 297.3 0 2 180298..33 2.0 3,β 724399..33 4 n- 979.3 e - 0 2 - p u ol d o I - 0 3 0 0 1. 689.4 0 5 0 1. 661.5 H O 6 I O H 3 7 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry M This journal is © The Royal Society of Chemistry 2013 P P 000.0 0 587.11 947.41 063.51 710.61 311.61 472.81 719.02 747.62 789.62 563.72 679.72 981.92 070.33 167.33 252.43 141.73 602.73 696.83 058.83 149.04 907.24 508.34 0 608.74 5 233.05 145.05 742.55 543.06 s m t 499.67 /3 759.87 Cl D C , ) 8 ( ol di 0 - 0 8 1 2 , β 3 - n e - 620.211 0 2 - p u ol d o I - 0 3 0 5 1 069.151 H O I O 0 H 0 2 4 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry M This journal is © The Royal Society of Chemistry 2013 P P 0 0 596.0 8. 3 107.0 037.0 357.0 468.0 159.0 1 420.1 380.1 703.1 244.1 065.1 787.1 169.1 000.2 902.2 542.2 372.2 2 082.2 0 782.2 0 803.2 2. 713.2 323.2 453.2 073.2 093.2 504.2 624.2 244.2 s m t / D O 1 3 3 1.0 D 490.3 7 C 211.3 0 814311..33 1. ),8 142.3 ( 872.3 ol 303.3 di - 0 8 0 2 0 1. ,β 0 3 337.3 2. n- 077.3 e 4 - 0 379.3 2 500.4 - 810.4 p 150.4 u ol d o I - 0 3 0 398.4 0 1. 799.4 5 1 0 1. 771.5 H O 6 I O H 7 5 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry M This journal is © The Royal Society of Chemistry 2013 P P 000.0 0 806.11 362.51 851.61 016.61 557.61 464.91 411.22 850.82 221.82 071.82 046.82 293.03 602.43 068.43 915.53 013.83 846.83 089.93 970.04 012.24 368.34 882.54 0 5 720.94 067.15 038.15 518.65 002.06 s m t / D O 756.97 3 D C , ) 8 ( ol di 0 - 0 8 1 2 , β 3 - n e - 453.211 0 2 - p u ol d o I - 0 3 0 5 1 470.451 H O I O H 0 0 2 6 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry M This journal is © The Royal Society of Chemistry 2013 P P 000.0- 729.0 659.0 799.0 0 810.1 860.1 742.1 782.1 443.1 754.1 0 947.1 0 977.1 7. 197.1 3 608.1 718.1 758.1 488.1 729.1 730.2 840.2 670.2 980.2 401.2 511.2 2 841.2 091.2 722.2 4 046433..22 2.0 073.2 683.2 693.2 00 214.2 1. 224.2 934.2 664.2 s 374.2 m 894.2 t 815.2 /3 525.2 Cl 055.2 048.2 00 D 858.2 2. C 878.2 , 598.2 4 )9 619.2 ( 139.2 al - 8 2 119.3 n- 249.3 e 229699..33 02 0- 510.5 00 1. p-2 702.5 1. u ol x o - 3 - o d 6 o I - 0 3 372.7 8 O H I 1 0 046.9 1. 446.9 O 0 1 7 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry M This journal is © The Royal Society of Chemistry 2013 P P 0 000.0- 196.01 002.41 777.51 299.51 006.91 320.12 373.12 916.62 597.62 148.82 060.92 458.23 059.23 166.33 601.43 988.63 656.83 536.93 987.04 216.24 207.34 713.74 0 925.94 5 697.94 619.45 243.95 120.77 s m t / 3 Cl D C , 0 )9 10 ( al - 8 2 - 334.211 n e - 0 2 - p u ol x o - 3 - o d o I - 0 50 3 806.151 1 O H 0 0 I 2 239.502 659.712 O 8 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry M This journal is © The Royal Society of Chemistry 2013 P P 3 4 4. 5 666.0 796.0 357.0 528.0 839.0 1 569.0 889.0 O 152.1 H2 083.1 554.1 x 494.1 035.1 865.1 506.1 546.1 796.1 727.1 667.1 308.1 849.1 379.1 889.1 510.2 2 730.2 651.2 661.2 591.2 602.2 342.2 s m 872.2 782.2 /t 423.2 3 Cl D C , ) 0 518864999...222 1.00 3 d(1 082909..32 3 ci 056310..33 1.0 ca 871.3 oi 691.3 - 412.3 8 2 - n e - 0 2 2.00 up- yl x 319.3 4 o 449.3 r 269.3 d y 299.3 h - β 3 - o d o I - 0 3 0 0 000.5 1. 5 0 0 1. 981.5 O H O 6 I O H 9 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry M This journal is © The Royal Society of Chemistry 2013 P P 000.0 0 531.11 217.41 943.51 570.61 051.61 762.81 239.02 855.62 183.72 489.72 207.92 110.23 884.33 133.43 258.63 002.73 393.83 607.83 458.83 986.04 224.24 643.34 0 5 264.05 990.15 s 203.55 m 762.65 t / 3 Cl D C , ) 0 600.77 1 769.87 ( d ci a c oi - 8 2 - 0 n 0 e 1 - 0 2 - p u yl 312.211 x o r d y h - β 3 - o d o I - 0 3 0 5 1 592.251 O H O I 757.971 O H 0 0 2 10

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Electrophilic Monoiodination of Terminal Alkenes. Sergiy V. Yemets,a Tatyana E. Shubinab and Pavel A. Krasutsky*a a University of Minnesota, Natural
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