This journal is The Royal Society of Chemistry 212 Supporting Information for Synthesis of Fused -Heterocycles via Tandem C-H Activation Ge Meng, Hong-Ying iu, Gui-Rong Qu, John S. Fossey, Jian-Ping Li,* and Hai-Ming Guo* College of Chemistry and Environmental Science, Key Laboratory of Green Chemical Media and Reactions of Ministry of Education, Henan ormal University, Xinxiang 4537, Henan, China. Fax: +86 373 3329276 E-mail: jplig@163.com; guohm518@hotmail.com General information...............s1 General procedure.................s2 Table for Intramolecular cyclisation of purines and benzimidazoles with iodobenzene...s3 Characterization of compounds..................s4 References..................S1 Copies of 1 H and 13 C MR spectra.................s11 General information: MR spectra were recorded with a 4 MHz spectrometer for 1 H MR, 1 MHz for 13 C MR. Chemical shifts δ are given in ppm relative to the residual signals of tetramethylsilane in CDCl 3 or deuterated solvent CDCl 3 for 1 H and 13 C MR. Multiplicities are reported as follows: singlet (s), doublet (d), triplet (t), multiplet (m). High resolution mass spectra were taken with a 3 mass spectrometer, using Waters Q-TofMS/MS system. For column chromatography silica gel (2-3 mesh) was used as the stationary phase. All reactions were monitored by thin layer chromatography (TLC). All reagents were purchased from commercial sources and purified commonly before used. All Starting materials were synthesized by Suzuki cross-coupling reactions according to references 1 and 2. S1
This journal is The Royal Society of Chemistry 212 General procedure for the intramolecular cyclization of 2, 6-substituted-9-benzyl purine. A 25 ml Schlenk tube, containing a Teflon stirbar, was charged with 2, 6-substituted-9-benzyl purine (.3 mmol), Pd(OAc) 2 (.3 mmol, 6.9 mg) and AgOAc (.6 mmol, 1.2 mg), then AcOH (1.5 ml) was added and the reaction mixture was heated at 11 o C for indicated hours. The resulting mixture was cooled down to room temperature, filtered through a pad of celite, and the celite was rinsed with copious EtOAc. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: petroleum ether/etoac) affording the corresponding intramolecular cyclization product. General procedure for the intramolecular cyclization of 1-benzyl benzimidazole. A 25 ml Schlenk tube, containing a Teflon stirbar, was charged with 1-benzyl benzimidazole (.3 mmol), Pd(OAc) 2 (.3 mmol, 6.9 mg) and AgOAc (.6 mmol, 1.2 mg), then AcOH (1.5 ml) was added and the reaction mixture was heated at 11 o C for indicated hours. The resulting mixture was cooled down to room temperature, filtered through a pad of celite, and the celite was rinsed with copious EtOAc. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: petroleum ether/etoac) affording the corresponding intramolecular cyclization product. General procedure for the intramolecular cyclization of purines and benzimidazoles with iodobenzene A 25 ml Schlenk tube, containing a Teflon stirbar, was charged with substrate (.3 mmol), Pd(OAc) 2 (.3 mmol, 6.9 mg), AgOAc (.6 mmol, 1.2 mg) and PhI (9 mmol, 1.836 g), then AcOH (1.5 ml) was added and the reaction mixture was heated at 11 o C~12 o C for indicated hours. The resulting mixture was cooled down to room temperature, filtered through a pad of celite, and the celite was rinsed with copious EtOAc. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: petroleum ether/etoac) affording the corresponding intramolecular cyclization product. S2
This journal is The Royal Society of Chemistry 212 Table for Intramolecular cyclisation of purines and benzimidazoles with iodobenzene a entry substrate product yield/% b 1 c 45 2 63 3 69 4 49 5 79 a Unless otherwise mentioned, all of the reactions were carried out with 1a (.3 mmol), catalyst (5 mol %), AgOAc (2 equiv), AcOH (1.8 ml) in a Schlenk tube at 11 o C for 36 h. b Isolated yield. c 12 o C for 48 h. S3
This journal is The Royal Society of Chemistry 212 Characterization of compounds 4-methoxy-1H-isoindolo[2,1-e]purine (2a): White solid. mp 183-185 o C. 1 H MR (4 MHz, CDCl 3 ) δ 8.53 (s, 1H), 8.1 (t, J = 4.4 Hz, 1H), 7.63 (t, J = 4. Hz, 1H), 7.58-7.53 (m, 2H), 5.18 (s, 2H), 4.23 (s, 3H); 13 C MR (1 MHz, CDCl 3 ) δ 16.8, 157.6, 151.4, 15.7, 143.5, 13.4, 129., 128.3, 125.9, 124.1, 122.3, 54.1, 47.1; HRMS: calcd for C 13 H 11 4 O [M+H] + 239.933, found 239.929. 4-methyl-1H-isoindolo[2,1-e]purine (2b): Light yellow solid. mp 175-177 o C. 1 H MR (4 MHz, CDCl 3 ) δ 8.77 (s, 1H), 8.11 (t, J = 4. Hz, 1H), 7.61 (d, J = 4.8 Hz, 1H), 7.57-7.54 (m, 2H), 5.15 (s, 2H), 2.88 (s, 3H); 13 C MR (1 MHz, CDCl 3 ) δ 159.1, 158.4, 151.5, 149.4, 143.9, 137.9, 131., 129.1, 127.9, 124.3, 122.7, 46.9, 19.7; HRMS: calcd for C 13 H 11 4 [M+H] + 223.984, found 223.986. 4-(piperidin-1-yl)-1H-isoindolo[2,1-e]purine (2c): Light yellow solid. mp 18-182 o C. 1 H MR (4 MHz, CDCl 3 ) δ 8.32 (s, 1H), 8.1 (d, J = 7.2 Hz, 1H), 7.58 (d, J = 6.8 Hz, 1H), 7.51-7.48 (m, 2H), 5.8 (s, 2H), 4.3 (s, 4H), 1.75 (s, 6H); 13 C MR (1 MHz, CDCl 3 ) δ 153.9, 153.4, 151.9, 149.5, 143.2, 129.5, 128.9, 128.6, 124.1, 121.7, 46.7, 46.4, 29.7, 26.2, 24.9; HRMS: calcd for C 17 H 18 5 [M+H] + 292.1562, found 292.1563. 4-ethoxy-1H-isoindolo[2,1-e]purine (2d): White solid. mp 188-19 o C. 1 H MR (4 MHz, CDCl 3 ) δ 8.46 (s, 1H), 8.6 (t, J = 4.2 Hz, 1H), 7.57 (t, J = 3.8 Hz, 1H), 7.51-7.49 (m, 2H), 5.12 (s, 2H), 4.68-4.63 (m, 2H), 1.53 (t, J =7.2 Hz, S4
This journal is The Royal Society of Chemistry 212 3H); 13 C MR (1 MHz, CDCl 3 ) δ 16.5, 157.4, 151.4, 15.7, 143.5, 13.3, 129., 128.3, 125.8, 124.1, 122.3, 63.1, 47., 14.6; HRMS: calcd for C 14 H 13 4 O [M+H] + 253.189, found 253.191. 2,4-dimethoxy-1H-isoindolo[2,1-e]purine (2e): Light yellow solid. mp 2-22 o C. 1 H MR (4 MHz, CDCl 3 ) δ 7.94-7.92 (m, 1H), 7.5-7.49 (m, 1H), 7.46-7.42 (m, 2H), 4.99 (s, 2H), 4.13 (s, 3H), 4. (s, 3H); 13 C MR (1 MHz, CDCl 3 ) δ 161.6, 161.2, 156., 152., 143.1, 129.8, 128.8, 128.4, 124., 121.8, 121.3, 55., 54.1, 46.8; HRMS: calcd for C 14 H 13 4 O 2 [M+H] + 269.139, found 269.134. 2-ethoxy-4-methoxy-1H-isoindolo[2,1-e]purine (2f): White solid. mp 19-192 o C. 1 H MR (4 MHz, CDCl 3 ) δ 7.99 (d, J = 6.4 Hz, 1H), 7.54 (d, J = 7.6 Hz, 1H), 7.48-7.45 (m, 2H), 5.3 (s, 2H), 4.66-4.6 (m, 2H), 4.2 (s, 3H), 1.51 (t, J = 7. Hz, 3H); 13 C MR (1 MHz, CDCl 3 ) δ 161.3, 161.2, 156., 152.1, 143.2, 129.8, 128.8, 128.5, 124., 121.9, 121.4, 63.1, 55.1, 46.8, 14.6; HRMS: calcd for C 15 H 15 4 O 2 [M+H] + 283.1195, found 283.1199. -benzyl-4-methoxy-1h-isoindolo[2,1-e]purin-2-amine (2g): Light yellow solid. mp 216-218 o C. 1 H MR (4 MHz, CDCl 3 ) δ 7.98 (d, J = 7.2 Hz, 1H), 7.54-7.26 (m, 8H), 5.39 (s, 1H), 4.98 (s, 2H), 4.7 (d, J = 5.6 Hz, 2H), 4.7 (s, 3H); 13 C MR (1 MHz, CDCl 3 ) δ 161.2, 158.6, 154.4, 152.3, 143., 139.6, 129.3, 129., 128.8, 128.5, 127.6, 127.1, 124., 121.6, 119.5, 53.6, 46.5, 46.1; HRMS: calcd for C 2 H 18 5 O [M+H] + 344.1511, found 344.151. S5
This journal is The Royal Society of Chemistry 212 -benzyl-4-ethoxy-1h-isoindolo[2,1-e]purin-2-amine (2h): Light yellow solid. mp 165-167 o C. 1 H MR (4 MHz, CDCl 3 ) δ 8. (d, J = 7.2 Hz, 1H), 7.55-7.32 (m, 8H), 5.37-5.34 (m, 1H), 4.99 (s, 2H), 4.69 (d, J = 5.6 Hz, 2H), 4.59-4.52 (m, 2H), 1.46 (t, J = 7. Hz, 2H); 13 C MR (1 MHz, CDCl 3 ) δ 161., 158.5, 154.3, 152.2, 143., 139.6, 129.3, 129., 128.7, 128.5, 127.5, 127.1, 124., 121.6, 119.4, 62.5, 46.5, 46.1, 14.6; HRMS: calcd for C 21 H 2 5 O [M+H] + 358.1668, found 358.1666.,-dibenzyl-4-methoxy-1H-isoindolo[2,1-e]purin-2-amine (2i): Light yellow solid. mp 14-142 o C. 1 H MR (4 MHz, (CD 3 ) 2 SO) δ 7.86-7.85 (m, 1H), 7.64 (d, J = 6. Hz, 1H), 7.51-7.5 (m, 2H), 7.31-7.3 (m, 8H), 7.24-7.23 (m, 2H), 5.11 (s, 2H), 4.87 (s, 3H), 3.91 (s, 3H); 13 C MR (1 MHz, CDCl 3 ) δ 16.7, 158.7, 154.4, 152.8, 143.1, 138.9, 129.2, 129., 128.7, 128.4, 127.7, 126.9, 123.9, 121.6, 118.7, 53.5, 49.8, 46.5; HRMS: calcd for C 27 H 24 5 O [M+H] + 434.1981, found 434.1978.,-dibenzyl-4-ethoxy-1H-isoindolo[2,1-e]purin-2-amine (2j): Light yellow solid. mp 145-147 o C. 1 H MR (4 MHz, (CD 3 ) 2 SO) δ 8.2 (d, J = 7.2 Hz, 1H), 7.51-7.42 (m, 3H), 7.35-7.24 (m, 1H), 4.96 (s, 2H), 4.93 (s, 4H), 4.53-4.47 (m, 2H), 1.41 (t, J = 7. Hz, 3H); 13 C MR (1 MHz, CDCl 3 ) δ 16.5, 158.7, 154.3, 152.8, 143.1, 139., 129.1, 128.7, 128.4, 127.7, 126.9, 123.9, 121.5, 118.7, 62.3, 49.7, 46.5, 14.5; HRMS: calcd for C 28 H 26 5 O [M+H] + 448.2137, found 448.2133. S6
This journal is The Royal Society of Chemistry 212 4-methoxy-7-methyl-1H-isoindolo[2,1-e]purine (2k): White solid. mp 22-222 o C. 1 H MR (4 MHz, CDCl 3 ) δ 8.51 (s, 1H), 7.88 (s, 1H), 7.48 (d, J = 7.6 Hz, 1H), 7.34 (d, J = 8. Hz, 1H), 5.11 (s, 2H), 4.22 (s, 3H), 2.49 (s, 3H); 13 C MR (1 MHz, CDCl 3 ) δ 16.7, 157.7, 151.3, 15.7, 14.7, 139.1, 131.4, 128.3, 125.8, 123.8, 122.7, 54.1, 46.9, 21.5; HRMS: calcd for C 14 H 13 4 O [M+H] + 253.189, found 253.185. 4-methoxy-1-methyl-1H-isoindolo[2,1-e]purine (2l): Light yellow solid. mp 165-167 o C. 1 H MR (4 MHz, CDCl 3 ) δ 8.53 (s, 1H), 8.8-8.6 (m, 1H), 7.55-7.53 (m, 3H), 5.47-5.42 (m, 1H), 4.22 (s, 3H), 1.89 (d, J = 6.8 Hz, 3H); 13 C MR (1 MHz, CDCl 3 ) δ 16.7, 156.6, 151.3, 15.7, 149.5, 13.5, 129., 127.6, 126.1, 123.1, 122.3, 55.9, 54.1, 18.9; HRMS: calcd for C 14 H 13 4 O [M+H] + 253.189, found 253.19. 11-methoxy-5,6-dihydropurino[8,9-a]isoquinoline (2m): White solid. mp 1-12 o C. 1 H MR (4 MHz, CDCl 3 ) δ 8.55 (s, 1H), 8.37 (d, J = 7.6 Hz, 1H), 7.45 (t, J = 4. Hz, 2H), 7.36 (d, J = 6.4 Hz, 1H), 4.48 (t, J = 6.8 Hz, 2H), 4.25 (s, 3H), 3.31 (t, J = 6.8 Hz, 2H); 13 C MR (1 MHz, CDCl 3 ) δ 152.2, 151.5, 142., 138.4, 134.8, 132.2, 131., 129.7, 128.2, 127.8, 125.8, 54.2, 47.3, 21.1; HRMS: calcd for C 14 H 13 4 O [M+H] + 253.189, found 253.185. 12-methoxy-6,7-dihydro-5H-benzo[3,4]azepino[1,2-e]purine (2n): White solid. mp 9-92 o C. 1 H MR (4 MHz, CDCl 3 ) δ 8.53 (s, 1H), 8.-7.98 (m, 1H), S7
This journal is The Royal Society of Chemistry 212 7.45-7.41 (m, 2H), 7.33 (d, J = 6.8 Hz, 1H), 4.26-4.22 (m, 5H), 2.79 (t, J = 7. Hz, 2H), 2.42 (t, J = 7. Hz, 2H); 13 C MR (1 MHz, CDCl 3 ) δ 16.7, 154., 153., 151.4, 139., 13.8, 129.9, 129.7, 129.6, 127.3, 121.5, 54.2, 4.2, 3.8, 3.1; HRMS: calcd for C 15 H 15 4 O [M+H] + 267.1246, found 267.1245. 11H-benzo[4,5]imidazo[2,1-a]isoindole (4a): Light yellow solid. mp 18-182 o C. 1 H MR (4 MHz, CDCl 3 ) δ 8.9 (d, J = 6.8 Hz, 1H), 7.85-7.82 (m, 1H), 7.57 (t, J = 8. Hz, 1H), 7.51 (t, J = 7.8 Hz, 2H), 7.47-7.44 (m, 1H), 7.31-7.28 (m, 2H), 5.6 (s, 2H); 13 C MR (1 MHz, CDCl 3 ) δ 158.4, 148.2, 143.5, 132.6, 129.5, 129.2, 128.6, 123.8, 122.6, 122.1, 121.9, 12.4, 19.3, 47.1; HRMS: calcd for C 14 H 11 2 [M+H] + 27.922, found 27.923. 5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline (4b): White solid. mp 115-117 o C. 1 H MR (4 MHz, CDCl 3 ) δ 8.29 (t, J = 4.2 Hz, 1H), 7.84-7.81 (m, 1H), 7.42-7.37 (m, 2H), 7.36-7.31 (m, 1H), 7.28 (t, J = 4.8 Hz, 2H), 4.28 (t, J = 7. Hz, 2H), 3.24 (t, J = 6.8 Hz, 2H); 13 C MR (1 MHz, CDCl 3 ) δ 149.1, 143.8, 134.6, 134.3, 13.2, 128.1, 127.7, 126.6, 125.6, 122.7, 122.4, 119.7, 19.1, 4.4, 28.2; HRMS: calcd for C 15 H 13 2 [M+H] + 221.179, found 221.18. 6,7-dihydro-5H-benzo[c]benzo[4,5]imidazo[1,2-a]azepine (4c): White pasty. 1 H MR (4 MHz, CDCl 3 ) δ 7.8-7.97 (m, 1H), 7.89-7.86 (m, 1H), 7.44-7.37 (m, 3H), 7.32-7.27 (m, 3H), 4.1 (t, J = 6.8 Hz, 2H), 2.77 (t, J = 7. Hz, 2H), 2.43-2.36 (m, 2H); 13 C MR (1 MHz, CDCl 3 ) δ 154.4, 143.1, 138.8, 135.4, 13.8, 13.3, 129.5, 129.4, 127.3, 122.5, 122.1, 119.9, 18.9, 41.3, 3.9, 3.6; HRMS: calcd for C 16 H 15 2 [M+H] + 235.1235, found 235.1237. S8
This journal is The Royal Society of Chemistry 212 14-phenyl-9H-dibenzo[3,4:5,6]azepino[1,2-e]purine (6a): Light yellow solid. mp 173-175 o C. 1 H MR (4 MHz, CDCl 3 ) δ 8.77 (s, 1H), 8.7 (t, J = 4.2 Hz, 1H), 7.87 (d, J = 7.2 Hz, 1H), 7.62 (d, J = 6.4 Hz, 1H), 7.58-7.51 (m, 6H), 7.22-7.2 (m, 2H), 7.15-7.9 (m, 3H), 5.17 (s, 2H); 13 C MR (1 MHz, CDCl 3 ) δ 159.8, 158.3, 151.3, 15.5, 144., 142., 141.4, 137.5, 134.6, 131.1, 131., 13.9, 129.7, 129.3, 129., 128., 127.7, 127.3, 126.5, 124.2, 123., 46.9; HRMS: calcd for C 24 H 17 4 [M+H] + 361.1453, found 361.145. 14-(p-tolyl)-9H-dibenzo[3,4:5,6]azepino[1,2-e]purine (6b): Light yellow pasty. 1 H MR (4 MHz, CDCl 3 ) δ 8.75 (s, 1H), 8.8-8.6 (m, 1H), 7.78 (d, J = 8. Hz, 1H), 7.6 (d, J = 6. Hz, 1H), 7.57-7.54 (m, 2H), 7.36 (t, J = 8.2 Hz, 1H), 7.21-7.18 (m, 2H), 7.14-7.8 (m, 3H), 5.16 (s, 2H), 2.48 (s, 3H); 13 C MR (1 MHz, CDCl 3 ) δ 159.6, 158.4, 151.3, 15.5, 144., 141.8, 141.5, 139.7, 137.5, 131.8, 131.7, 131.1, 13.9, 129.2, 128.1, 127.7, 126.4, 124.2, 123., 46.9, 21.4; HRMS: calcd for C 25 H 19 4 [M+H] + 375.161, found 375.165. 9,1-dihydrodibenzo[c,e]benzo[4,5]imidazo[1,2-a]azocine (6c): Light yellow solid. mp 136-138 o C. 1 H MR (4 MHz, CDCl 3 ) δ 7.54 (d, J = 8. Hz, 1H), 7.54 (d, J = 8. Hz, 1H), 7.39 (s, 5H), 7.34-7.32 (m, 3H), 7.23 (d, J = 8. Hz, 1H), 7.18-7.14 (m, 1H), 4.37 (t, J = 6.6 Hz, 2H), 3.26 (t, J = 6.6 Hz, 2H); 13 C MR (1 MHz, CDCl 3 ) δ 148., 143.4, 141.9, 141.7, 136.6, 133.7, 131.2, 129.5, 129.3, 127.7, 127.2, 126.9, 124.8, 122.5, 121.8, 12.4, 18.6, 4.1, 3.; HRMS: calcd for C 21 H 17 2 [M+H] + 297.1392, found 297.139. S9
This journal is The Royal Society of Chemistry 212 1-methoxy-16,17-dihydro-15H-dibenzo[3,4:5,6]azonino[1,2-e]purine (6d): White solid. mp 19-192 o C. 1 H MR (4 MHz, CDCl 3 ) δ 8.5 (s, 1H), 7.5 (t, J = 7.4 Hz, 1H), 7.43 (d, J = 6.8 Hz, 1H), 7.32 (d, J = 7.2 Hz, 1H), 7.24-7.22 (m, 3H), 7.14-7.11 (m, 2H), 4.38 (s, 2H), 4.6 (s, 3H), 2.62 (t, J = 6.8 Hz, 2H), 2.37-2.3 (m, 2H); 13 C MR (1 MHz, CDCl 3 ) δ 16.7, 152., 151.9, 151.3, 147.6, 143.3, 14.5, 139.8, 13.4, 129.6, 129.1, 128.1, 127.9, 127., 121.3, 54.3, 39.2, 3.6, 3.1; HRMS: calcd for C 21 H 19 4 O [M+H] + 343.1559, found 343.1557. 16,17-dihydro-15H-dibenzo[c,e]benzo[4,5]imidazo[1,2-a]azonine (6e): Light yellow solid. mp 12-122 o C. 1 H MR (4 MHz, CDCl 3 ) δ 7.63 (d, J = 8. Hz, 1H), 7.51-7.45 (m, 2H), 7.41 (d, J = 8. Hz, 1H), 7.3 (t, J = 6.4 Hz, 2H), 7.23-7.15 (m, 6H), 4.3 (s, 2H), 2.6 (t, J = 6.4 Hz, 2H), 2.33 (t, J = 6.6 Hz, 2H); 13 C MR (1 MHz, CDCl 3 ) δ 152.4, 143.3, 142.9, 14.8, 139.7, 133.8, 13., 129.5, 129.1, 128.8, 128.1, 128., 127.9, 126.9, 122.2, 121.6, 18.5, 4.2, 3.7, 3.5; HRMS: calcd for C 22 H 19 2 [M+H] + 311.1548, found 311.1552. References: 1. Černǎ, I.; Pohl, R.; Klepetářová, B.; Hocek, M. J. Org. Chem. 28, 73, 948-954. 2. Lakshman, M.K.; Hilmer, J.H.; Martin, J.Q.; Keeler, J.C.; Dinh, Y.Q.V.; gassa, F..; Russon, L.M. J. Am. Chem. Soc. 21, 123, 779-7787. S1
This journal is The Royal Society of Chemistry 212 Copies of 1 H and 13 C MR Spectrum 1 H MR Spectrum for 2a 8.52 8.94 8.86 8.84 8.72 7.613 7.64 7.553 7.548 7.544 7.537 7.532 7.26 2 15 1 5.94.99 2.99-5 8.5 8. 7.5 6 8.52 8.94 8.86 8.84 8.72 7.613 7.64 7.553 7.548 7.544 7.537 7.532 7.26 5.164.99.94 2.99 2.3 4.216 3. 1.739 1.242.869 5 4 3 2 1-1 (f1) 4.23 (f1) 2.447 (f1) 2.22 ZG3 293.46 umber of Scans: 16 Wed ov 24 9:11:39 AM 15. 1. 5.. 13 C MR Spectrum for 2a 16.79 157.573 151.377 15.657 143.497 13.391 129.1 128.253 125.894 124.114 122.347 15 1 5-5 16 15 14 13 12 16.79 157.573 151.377 15.657 143.497 13.391 129.1 128.253 125.894 124.114 122.347 77.347 77.29 76.711 54.129 47.57 5 (f1) 1.641 (f1).6521 ZGDC3 296.86 umber of Scans: 78 2 15 1 5 S11
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 2b 8.772 8.12 8.18 8.1 7.613 7.61 7.573 7.56 7.55 7.539 1 5 1.96 1. 1.1 1. 8.5 8. 7.5 CH 3 8.772 8.12 8.18 8.1 7.613 7.61 7.573 7.56 7.55 7.539 5.151 2.881 1 5 (f1) 4.22 (f1) 2.287 ZG3 29.16 umber of Scans: 4 3.11 2.7 1.99 3.11 1. 1.96 1.1 1. -5 1. 5.. 13 C MR Spectrum for 2b 159.12 158.438 151.49 149.42 143.892 137.919 13.995 129.19 127.93 124.28 122.689 25 2 15 1 5-5 16 15 14 13 12 11 CH 3 159.12 158.438 151.49 149.42 143.892 137.919 13.995 129.19 127.93 124.28 122.689 46.895 19.686 6 5 4 3 2 1 (f1) 1.641 (f1).6521 ZGDC3 289.66 umber of Scans: 115-1 -2 2 15 1 5 S12
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 2c 8.318 8.19 8.1 7.588 7.571 7.512 7.493 7.476 7.262 4 3 2 1 1. 1.2 1.7 2.13-1 8.318 8. 8.19 8.1 7.588 7.571 7.512 7.493 7.476 7.262 1.7 2.13 1.2 1. 5.82 2.11 4.32 3.98.49 2.168 1.745 6.54 7.5 6 5 4 3 2 1-1 -2 (f1) 4.22 (f1) 2.287 ZG3 296.96 umber of Scans: 8 Fri Sep 23 1:1:19 PM 1. 5.. 13 C MR Spectrum for 2c 153.942 153.44 151.855 149.512 143.236 129.462 128.94 128.64 124.84 121.73 6 5 4 3 2 1-1 -2 16 15 14 13 12 153.942 153.44 151.855 149.512 143.236 129.462 128.94 128.64 124.84 121.73 46.74 46.478 29.682 26.29 24.887 5 (f1) 1.641 (f1).6521 ZGDC3 295.46 umber of Scans: 49 Tue Oct 11 6:46:22 PM 2 15 1 5 S13
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 2d 8.462 8.66 8.57 8.45 7.583 7.572 7.564 7.58 7.498 7.487 5 4 3 2 1-1 1. 1.3.97 2.21-2 8.5 8. 7.5 7. OC 2 H 5 8.462 8.66 8.57 8.45 7.583 7.572 7.564 7.58 7.498 7.487 5.121 4.681 4.663 4.645 4.628 1.543 1.525 1.57 1 5 (f1) 4.22 (f1) 2.287 ZG3 29.16 umber of Scans: 4 3.24 2.17 2.15.97 2.21 1.3 1. 1. 5.. 13 C MR Spectrum for 2d 16.539 157.426 151.381 15.656 143.483 13.337 128.983 128.252 125.812 124.115 122.345 2 15 1 5-5 16 15 14 13 12 OC 2 H 5 16.539 157.426 151.381 15.656 143.483 13.337 128.983 128.252 125.812 124.115 122.345 63.59 47.11 14.65 1 5 (f1) 1.641 (f1).6521 ZGDC3 289.76 umber of Scans: 78 2 15 1 5 S14
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 2e 7.941 7.936 7.921 7.55 7.491 7.487 7.458 7.437 7.43 7.422 7.262 3 2 1 1. 1.1 1.99-1 8. 7.5 7. 7.941 7.936 7.921 7.55 7.491 7.487 7.458 7.437 7.43 7.422 1. 3.7 1.1 1.99 7.262 4.985 2.3 4.133 3.9 3.1 4.4 5 4 3 2 1-1 -2 (f1) 4.22 (f1) 2.287 ZG3 3.16 umber of Scans: 8 Mon Jul 4 5:2:34 PM 1. 5.. 13 C MR Spectrum for 2e 161.553 161.225 156.45 151.998 143.14 129.755 128.776 128.428 123.96 121.783 121.337 5 16 15 14 13 12 161.553 161.225 156.45 151.998 143.14 129.755 128.776 128.428 123.96 121.783 121.337 55.35 54.93 46.768 3 2 1 (f1) 1.641 (f1).6521 ZGDC3 3.36 umber of Scans: 2 Tue Jul 5 4:23:18 PM -1 2 15 1 5 S15
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 2f 8.3 7.987 7.545 7.526 7.477 7.472 7.466 7.454 6 5 4 3 2 1-1 1. 1. 2.4-2 8. OC 2 H 5 8.3 7.987 7.545 7.526 7.477 7.472 7.466 7.454 3.1 1. 2.4 1. 5.28 4.655 4.637 4.619 4.61 2.5 2.3 3.9 4.15 2.149 1.524 1.57 1.489 3.8 7.5 1 5 (f1) 4.22 (f1) 2.287 ZG3 29.26 umber of Scans: 4 Fri Dec 16 7:49:56 PM 1. 5.. 13 C MR Spectrum for 2f 161.338 161.229 156.25 152.91 143.162 129.782 128.839 128.546 124.3 121.874 121.371 3 2 1-1 16 15 14 13 12 161.338 161.229 OC 2 H 5 156.25 152.91 143.162 129.782 128.839 128.546 124.3 121.874 121.371 63.117 55.71 46.783 14.558 1 (f1) 1.641 5 (f1).6521 ZGDC3 289.46 umber of Scans: 156 Thu Dec 22 1:34:4 AM 2 15 1 5 S16
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 2g 7.99 7.972 7.538 7.521 7.483 7.461 7.44 7.47 7.389 7.353 7.335 7.316 7.281 7.26 5.395 4.98 7.99 7.972 7.538 7.521 7.483 7.461 7.44 7.47 7.389 7.353 7.335 7.316 7.281 7.26 5.395 4.98 4.75 4.691 4.69 3.13 2.6 2.8 1. 8.46 1.6 8. 7. 6. 5. 4. 1.6 8.46 1. 2.8 4.75 4.691 2.6 4.69 3.13 H (f1) 4.22 (f1) 2.7132 (f1) 15.89 ZG3 29.26 umber of Scans: 16 9. 8. 7. 6. 5. 4. 3. 2. 1.. 13 C MR Spectrum for 2g 161.233 158.567 154.47 152.326 143.17 139.62 129.295 128.96 128.758 128.513 127.553 127.148 123.986 121.591 119.455 H 17 16 15 14 13 12 11 1 161.233 158.567 154.47 152.326 143.17 139.62 129.295 128.96 128.758 128.513 127.553 127.148 123.986 121.591 119.455 53.644 46.518 46.97 (f1) 1.641 (f1).6521 ZGDC3 292.66 umber of Scans: 21 2 15 1 5 S17
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 2h 5 8.16 7.998 7.545 7.527 7.54 7.486 7.465 7.443 7.425 7.42 7.385 7.353 7.335 7.317 7.281 7.262 5.372 5.361 5.34 4.99 4.696 4.682 4.588 4.571 4.554 4 518 4 3 2 1 1. 8.17.99 1.88 1.99 2.17-1 8. 7.5 7. 6.5 6. 5.5 5. 4.5 8.16 7.998 7.545 7.527 7.54 7.486 7.465 7.443 7.425 7.42 7.385 7.353 7.335 7.317 7.281 7.262 5.372 5.361 5.34 OC 2 H 5 H 4.99 4.696 4.682 4.588 4.571 4.554 4.536 4.518 2.943 2.919 2.16 1.733 1.722 1.72 1.718 1 5 (f1) 4.22 (f1) 2.287 ZG3 294.76 umber of Scans: 8 Wed Oct 26 5:31:8 PM 3.25 1.99 2.17 1.88.99 8.17 1. 1. 5.. 13 C MR Spectrum for 2h 16.995 158.495 154.345 152.222 143.29 139.635 129.281 128.948 128.748 128.51 127.484 127.114 123.977 121.645 119.4 25 2 15 1 5-5 16 15 14 13 12 OC 2 H 5 H 16.995 158.495 154.345 152.222 143.29 139.635 129.281 128.948 128.748 128.51 127.484 127.114 123.977 121.645 119.4 62.59 46.534 46.83 14.574 5 (f1) 1.641 (f1).6521 ZGDC3 296.26 umber of Scans: 3166 Thu ov 3 7:32:17 AM 2 15 1 5 S18
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 2i 4 7.863 7.859 7.845 7.648 7.633 7.514 7.56 7.51 7.498 7.39 7.3 7.243 7.233 3 2 1 1. 1.4 2.13 8.1 2.14-1 7.9 7.8 7.7 7.6 7.5 7.4 7.3 7.2 3 7.863 7.859 7.845 7.648 7.633 7.514 7.56 7.51 7.498 1.36 8.1 2.14 1.4 2.13 1. 7.39 7.3 7.243 7.233 3.94 3.53 3.77 3.31 3.47 3.33 1.96 5.15 4.868 2.98 3.98 3.32 2.483 2 1-1 (f1) 4.22 (f1) 2.287 ZG3 29.56 umber of Scans: 4 Fri Dec 16 7:53:54 PM 1. 5.. 13 C MR Spectrum for 2i 16.749 158.71 154.369 152.767 143.113 138.918 129.161 129.43 128.683 128.49 127.677 126.934 123.923 121.569 118.679 25 2 15 1 5-5 16 15 14 13 12 16.749 158.71 154.369 152.767 143.113 138.918 129.161 129.43 128.683 128.49 127.677 126.934 123.923 121.569 118.679 53.528 49.765 46.533 6 5 4 3 2 1-1 (f1) 1.641 (f1).6521 ZGDC3 298.96 umber of Scans: 7 Wed Aug 31 5:26: PM 2 15 1 5 S19
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 2j 6 8.25 8.7 7.513 7.494 7.471 7.453 7.437 7.434 7.418 7.416 7.345 7.313 7.283 7.274 5 4 3 2 1-1 1. 3.42 8.61.98-2 8. 7.9 7.8 7.7 7.6 7.5 7.4 7.3 OC 2 H 5 8.25 8.7 7.513 7.494 7.471 7.453 7.437 7.434 7.418 7.416 7.345 7.313 7.283 7.274 4.957 4.931 4.527 4.59 4.491 4.473 1.426 1.49 1.391 1. 3.42 8.61.98 2.16 2.2 4.4 3.26.15 6 5 4 3 2 1-1 -2 (f1) 4.22 (f1) 2.287 ZG3 294.76 umber of Scans: 8 Wed Oct 26 5:28:43 PM 1. 5.. 13 C MR Spectrum for 2j 16.483 158.7 154.269 152.797 143.128 139.2 129.97 128.65 128.424 127.666 126.933 123.932 121.524 118.73 4 3 2 1-1 16 15 14 13 12 OC 2 H 5 16.483 158.7 154.269 152.797 143.128 139.2 129.97 128.65 128.424 127.666 126.933 123.932 121.524 118.73 62.317 49.744 46.484 14.546 5 (f1) 1.641 (f1).6521 ZGDC3 295.16 umber of Scans: 95 Wed ov 2 5:1:57 PM 2 15 1 5 S2
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 2k 1 8.59 7.878 7.491 7.472 7.351 7.331 5 1.4 1.3 1.2 1. 8.5 8. 7.5 H 3 C 8.59 7.878 7.491 7.472 7.351 7.331 5.112 4.215 2.486 2 15 1 5 (f1) 4.22 (f1) 2.287 ZG3 298.26 umber of Scans: 8 1. 1.3 1.4 1.2 2.3 3.8 3.3-5 1. 5.. 13 C MR Spectrum for 2k 16.721 157.696 151.262 15.688 14.78 139.136 131.364 128.278 125.849 123.771 122.664 25 2 15 1 5-5 H 3 C 16 16.721 157.696 151.262 15.688 14.78 139.136 131.364 128.278 15 125.849 123.771 122.664 14 54.118 46.867 21.495 13 6 5 4 3 2 1 12 (f1) 1.641 (f1).6521 ZGDC3 295.46 umber of Scans: 14-1 -2 2 15 1 5 S21
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 2l 8.526 8.8 8.76 8.67 8.57 7.549 7.544 7.526 15 1 5 1. 3.19-5 8.5 8. 7.5 CH 3 8.526 8.8 8.76 8.67 8.57 1.4 1. 3.19 7.549 7.544 7.526 5.466 5.449 5.432 5.416 1.7 3.19 3.2 4.218 1.897 1.88 3.22 3.1 25 2 15 1 5-5 (f1) 4.22 (f1) 2.287 ZG3 299.56 umber of Scans: 12-1 1. 5.. 13 C MR Spectrum for 2l 16.738 156.554 151.324 15.737 149.518 13.54 129.7 127.59 126.18 123.125 122.32 15 1 5-5 165. 16. 155. 15. 145. 14. 135. 13. 125. CH 3 16.738 156.554 151.324 15.737 149.518 13.54 129.7 127.59 126.18 123.125 122.32 55.918 54.58 18.923 6 5 4 3 2 1-1 (f1) 1.641 (f1).6521 ZGDC3 298.86 umber of Scans: 59-2 2 15 1 5 S22
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 2m 8.547 8.384 8.365 7.464 7.455 7.444 7.365 7.349 7.282 1 5 1..88 1.82.89-5 8.5 8. 7.5 8.547 8.384 8.365 1..88 7.464 7.455 7.444 7.365 7.349 7.282 4.498 4.481 4.464 1.82.89 2.72 2.12 4.247 3.328 3.311 3.294 1.9 25 2 15 1 5-5 (f1) 4.23 (f1) 2.447 (f1) 2.22 ZG3 297.36 umber of Scans: 4 Thu May 12 1:17:52 AM -1 15. 1. 5.. 13 C MR Spectrum for 2m 152.26 151.522 141.961 138.368 134.841 132.195 13.95 129.711 128.178 127.816 125.753 4 3 2 1-1 15. 145. 14. 135. 13. 125. 12. 115. 161.83 152.26 151.522 141.961 138.368 134.841 132.195 13.95 129.711 128.178 127.816 125.753 54.174 47.272 21.85 1 5 (f1) 1.641 (f1).6521 ZGDC3 298.96 umber of Scans: 111 Tue Jun 21 4:47:6 PM 2 15 1 5 S23
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 2n 8.534 7.998 7.996 7.98 7.977 7.453 7.449 7.435 7.431 7.426 7.411 7.48 7.338 7.321 7.262 15 1 5 1. 1.4 2.27 1.9-5 8.5 8. 7.5 8.534 7.998 7.996 7.98 7.977 7.453 7.449 7.435 7.431 7.426 7.411 7.48 7.338 7.321 7.262 1. 1.4 2.27 1.9 4.262 4.245 4.228 4.216 5.38 2.2 2.15 2.86 2.789 2.771 2.435 2.417 2.4 2 15 1 5-5 (f1) 4.22 (f1) 2.287 ZG3 298.46 umber of Scans: 16 Fri Aug 5 9:16:7 AM 1. 5.. 13 C MR Spectrum for 2n 16.78 153.988 152.997 151.449 138.956 13.819 129.878 129.629 129.587 127.344 121.47 1 5 16. 155. 15. 145. 14. 135. 13. 125. 16.78 153.988 152.997 151.449 138.956 13.819 129.878 129.629 129.587 127.344 121.47 54.16 4.22 3.788 3.135 5 4 3 2 1-1 (f1) 1.641 (f1).6521 ZGDC3 298.86 umber of Scans: 58 Wed Aug 31 4:17:38 PM 2 15 1 5 S24
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 4a 8.99 8.82 7.854 7.847 7.84 7.832 7.822 7.586 7.567 7.546 7.529 7.511 7.49 7.471 7.464 7.456 7.45 7.442 7.39 7.299 7.291 7.284 7.276 1 5 2.1 1.13 1.79 1.19.97 1. 8. 7.5 8.99 8.82 7.854 7.847 7.84 7.832 7.822 7.586 7.567 7.546 7.529 7.511 7.49 7.471 7.464 7.456 7.45 7.442 1.19 1.79 1.13 2.1 1.2.87.97 1. 2.7 7.39 7.299 7.291 7.284 7.276 5.6 5 4 3 2 1-1 (f1) 4.22 (f1) 2.287 ZG3 295.36 umber of Scans: 16 Tue Jun 7 11:25:56 AM -2 1. 5.. 13 C MR Spectrum for 4a 158.39 148.23 143.467 132.563 129.454 129.216 128.649 123.794 122.619 122.119 121.948 12.42 19.311 2 15 1 5-5 16 15 14 13 12 11 158.39 148.23 143.467 132.563 129.454 129.216 128.649 123.794 122.619 122.119 121.948 12.42 19.311 47.14 5 4 3 2 1-1 (f1) 1.641 (f1).6521 ZGDC3 295.36 umber of Scans: 28 Tue Oct 11 5:21:33 PM 2 15 1 5 S25
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 4b 8.297 8.293 8.276 7.836 7.83 7.826 7.814 7.418 7.42 7.386 7.373 7.37 7.355 7.351 7.343 7.339 7.331 7.321 7.311 7.294 7.279 7 27 261 5 2.41 1.24 1.92 1.1 1. 8. 7.5 8.297 8.293 8.276 7.836 7.83 7.826 7.814 7.418 7.42 7.386 7.373 7.37 7.355 7.351 7.343 7.339 7.331 7.321 7.311 7.294 7.279 7.27 1.92 1.24 2.45 2.41 1.1 1. 2.8 2.8 4.295 4.278 4.26 3.259 3.242 3.225 1 5 (f1) 4.22 (f1) 2.287 ZG3 289.36 umber of Scans: 8 Thu Dec 22 9:34:58 AM 1. 5.. 13 C MR Spectrum for 4b 149.73 143.847 134.614 134.276 13.15 128.91 127.75 126.59 125.576 122.665 122.443 119.695 19.76 2 15 1 5-5 15 14 13 12 11 149.73 143.847 134.614 134.276 13.15 128.91 127.75 126.59 125.576 122.665 122.443 119.695 19.76 77.431 77.113 76.795 4.363 28.199 2 1 (f1) 1.641 (f1).6521 ZGDC3 289.66 umber of Scans: 56 Thu Dec 22 9:49:51 AM -1 2 15 1 5 S26
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 4c 7.996 7.987 7.982 7.974 7.885 7.88 7.871 7.863 7.441 7.43 7.422 7.417 7.48 7.397 7.387 7.378 7.373 7.322 7.38 7.32 7.29 7.284 7.273 7.262 5 3. 3.3.99 1. 8. 7.5 7.996 7.987 7.982 7.974 7.885 7.88 7.871 7.863 7.441 7.43 7.422 7.417 7.48 7.397 7.387 7.378 7.373 7.322 7.38 7.32 7.29 7.284 7.273 7.262 6.5 3.3 3. 1..99 2.14 2.7 2.6 2.3 4.118 4.11 4.84 2.791 2.773 2.756 2.426 2.49 2.392 2.375 2.357 2 15 1 5-5 (f1) 4.22 (f1) 2.287 ZG3 297.76 umber of Scans: 8 Tue Oct 18 9:37:35 AM 1. 5.. 13 C MR Spectrum for 4c 154.49 143.19 154.49 143.19 138.837 135.353 138.837 135.353 13.765 13.255 129.495 129.463 127.31 122.536 122.125 119.933 18.945 5 15 14 13 12 11 13.765 13.255 129.495 129.463 127.31 122.536 122.125 119.933 18.945 41.288 3.851 3.626 15 1 5-5 (f1) 1.641 (f1).6521 ZGDC3 295.36 umber of Scans: 25 Tue Oct 11 4:42:29 PM 2 15 1 5 S27
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 6a 8.765 8.87 8.71 8.66 7.878 7.86 7.623 7.67 7.582 7.564 7.553 7.546 7.543 7.524 7.512 7.222 7.217 7.22 7.145 7.138 7.134 7.123 7 14 4 3 2 1-1 1. 1.6 1.6 1.6 5.6 2.28 3.46-2 8.5 8. 7.5 8.765 8.87 8.71 8.66 7.878 7.86 7.623 7.67 7.582 7.564 7.553 7.546 7.543 7.524 7.512 7.222 7.217 7.22 7.145 7.138 7.134 7.123 7.14 7.88 1.5 1. 2.28 3.46 1.6 5.6 1.6 1.6 2.19 5.174 1 5 (f1) 4.22 (f1) 2.287 ZG3 298.26 umber of Scans: 8 Wed Aug 31 2:58:44 PM 1. 5.. 13 C MR Spectrum for 6a 159.794 158.273 151.311 15.545 143.976 141.963 141.37 137.453 134.65 131.124 131.5 13.858 129.728 129.261 129.4 128.9 127.73 127.336 126.457 124.199 123.63 3 2 1-1 16. 155. 15. 145. 14. 135. 13. 125. 159.794 158.273 151.311 15.545 143.976 141.963 141.37 137.453 134.65 131.124 131.5 13.858 129.728 129.261 129.4 128.9 127.73 127.336 126.457 124.199 123.63 46.934 1 5 (f1) 1.641 (f1).6521 ZGDC3 298.6 umber of Scans: 22 Fri Sep 3 2:36:55 PM 2 15 1 5 S28
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 6b 8.746 8.8 8.72 8.65 8.6 7.79 7.77 7.612 7.597 7.572 7.558 7.553 7.544 7.535 7.376 7.355 7.335 7.213 7.29 7.193 7.177 7.167 7.159 7.139 7.133 7.118 7 99 81 3 2 1 1. 1.11 1.13 1.25 2.38 2.49 2.45 3.54-1 8.5 8. 7.5 7. 8.746 8.8 8.72 8.65 8.6 7.79 7.77 CH 3 7.612 7.597 7.572 7.558 7.553 7.544 7.535 7.376 7.355 7.335 7.213 7.29 7.193 7.177 7.167 7.159 7.139 7.133 7.118 7.99 7.81 5.158 2.53 2.482 1 5 (f1) 4.22 (f1) 2.287 ZG3 298.26 umber of Scans: 8 3.16 2.5 2.53 2.45 3.54 2.57 2.49 3.55 1.25 2.38 1.13 1.11 1. 1. 5.. 13 C MR Spectrum for 6b 159.612 158.411 151.33 15.463 143.954 141.846 141.535 139.728 137.475 131.778 131.657 131.148 13.918 129.241 129.181 129.7 128.8 127.658 126.372 124.176 123.37 4 3 2 1-1 16 15 14 13 CH 3 159.612 158.411 151.33 15.463 143.954 141.846 141.535 139.728 137.475 131.778 131.657 131.148 13.918 129.241 129.181 129.7 128.8 127.658 126.372 124.176 123.37 46.91 21.444 1 5 (f1) 1.641 (f1).6521 ZGDC3 297.76 umber of Scans: 298 2 15 1 5 S29
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 6c 7.546 7.526 7.433 7.413 7.389 7.337 7.324 7.319 7.262 7.244 7.224 7.175 7.157 7.14 7.138 1 5 1.1.82 3.2 4.89.95 1.2 7.5 7.4 7.3 7.2 7.1 7.546 7.526 7.433 7.413 7.389 7.337 7.324 7.319 7.262 7.244 7.224 7.175 7.157 7.14 7.138 4.386 4.369 4.353 3.2.82 1.1 1.2.95 4.89 2. 2.1 3.275 3.258 3.242 1 5 (f1) 4.22 (f1) 2.287 ZG3 3.16 umber of Scans: 8 Mon Jul 4 5:5:28 PM 1. 5.. 13 C MR Spectrum for 6c 147.968 143.41 141.864 141.727 136.645 133.73 131.183 129.461 129.251 127.729 127.182 126.94 124.833 122.58 121.754 12.447 18.559 2 15 1 5-5 15 14 13 12 11 147.968 143.41 141.864 141.727 136.645 133.73 131.183 129.461 129.251 127.729 127.182 126.94 124.833 122.58 121.754 12.447 18.559 4.79 3.46 3 2 1-1 (f1) 1.641 (f1).6521 ZGDC3 298.76 umber of Scans: 63 Wed Aug 31 5:51:8 PM 2 15 1 5 S3
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 6d 8.51 7.515 7.496 7.478 7.44 7.423 7.324 7.36 7.238 7.231 7.223 7.135 7.129 7.12 7.112 25 2 15 1 5-5 1. 1.16 1.9 1.17 3.21 2.11-1 8.5 8. 7.5 7. 8.51 7.515 7.496 7.478 7.44 7.423 7.324 7.36 7.238 7.231 7.223 7.135 7.129 7.12 7.112 4.378 4.6 2.632 2.615 2.598 2.37 2.353 2.336 2.319 2.32 15 1 5 (f1) 4.22 (f1) 2.287 ZG3 298.66 umber of Scans: 16 1. 1.16 1.14 1.17 3.21 2.11 1.9 3.23 1.93 2.19 2.12-5 1. 5.. 13 C MR Spectrum for 6d 16.746 151.989 151.888 151.297 147.564 143.253 14.488 139.764 13.429 129.64 129.147 128.112 127.898 126.955 121.27 1 5 16 15 14 13 12 16.746 151.989 151.888 151.297 147.564 143.253 14.488 139.764 13.429 129.64 129.147 128.112 127.898 126.955 121.27 54.317 39.232 3.611 3.12 3 2 1 (f1) 1.641 (f1).6521 ZGDC3 297.96 umber of Scans: 45-1 2 15 1 5 S31
This journal is The Royal Society of Chemistry 212 1 H MR Spectrum for 6e 7.637 7.617 7.51 7.49 7.473 7.468 7.464 7.448 7.422 7.42 7.316 7.32 7.284 7.262 7.233 7.225 7.218 7.199 7.179 7.161 7.154 4 3 2 1 1. 2.17 1.3 1.88 6.53-1 7.7 7.6 7.5 7.4 7.3 7.2 7.1 7.637 7.617 7.51 7.49 7.473 7.468 7.464 7.448 7.422 7.42 7.316 7.32 7.284 7.262 7.233 7.225 7.218 7.199 7.179 7.161 7.154 4.297 2.618 2.62 2.586 2.347 2.33 2.314 1. 2.17 1.3 1.88 6.53 1.89 2.2 2.3 1 5 (f1) 4.22 (f1) 2.287 ZG3 297.76 umber of Scans: 8 Thu Sep 29 11:4:16 AM -5 1. 5.. 13 C MR Spectrum for 6e 152.434 143.259 142.861 14.83 139.711 133.8 13.18 129.539 129.114 128.831 128.71 127.964 126.85 122.18 121.599 12.328 18.531 2 15 1 5-5 15 14 13 12 11 152.434 143.259 142.861 14.83 139.711 133.8 13.18 129.539 129.114 128.831 128.71 127.964 126.85 122.18 121.599 12.328 18.531 4.237 3.732 3.485 3 2 1 (f1) 1.641 (f1).6521 ZGDC3 297.66 umber of Scans: 42 Fri Sep 3 2:28:35 PM -1 2 15 1 5 S32