Four- and Five-membered Cobaltacycles by Regioselective Cyclometalation. of Benzylsulfide Derivatives via Co(V) intermediates
|
|
- Ἑστία Δουμπιώτης
- 5 χρόνια πριν
- Προβολές:
Transcript
1 Electronic Supplementary Information for Dalton Transactions This journal is The Royal Society of Chemistry 2008 Supporting Information for: Four- and Five-membered Cobaltacycles by Regioselective Cyclometalation of Benzylsulfide Derivatives via Co(V) intermediates Robert Beck *, Markus Frey, Sebnem Camadanli and Hans-Friedrich Klein [*] Dr. R. Beck, Dr. M. Frey, Dr. S. Camadanli, Prof. Dr. H.-F. Klein Eduard-Zintl-Institut für Anorganische und Physikalische Chemie Technische Universität Darmstadt, Petersenstraße 18, D Darmstadt [ ] Present Address: School of Chemistry and Chemical Engineering Shandong University, Shanda Nanlu 27, Jinan, People s Republic of China, Fax: (+86) , metallacycle@gmail.com, robert@sdu.edu.cn Experimental Section General Considerations. All air-sensitive and volatile materials were handled using standard vacuum techniques 1 and kept under argon. Air-sensitive samples were provided in capillaries sealed under vacuum and were analyzed by H. Kolbe Microanalytical Laboratory, Mülheim/Ruhr, Germany. The melting and decomposition points were measured on a Büchi 510 Melting point apparatus and are uncorrected. Air-sensitives substances were sealed in capillaries under 1 bar of Argon. Chemicals (Merck/Schuchardt) were used as purchased. S1
2 2 Literature methods were applied for the preparation of PMe 3 and [CoMe(PMe 3 ) 4 ] 3. IR spectra were obtained from as Nujol mulls between KBr plates using a Bruker FRA 106 spectrophotometer and were recorded in the range cm H, 13 C and 31 P NMR spectra were recorded with a Bruker DRX 500 spectrometer, 13 C{ 1 H} and 31 P{ 1 H} resonances were obtained with broad-band proton decoupling. Magnetic suscepitbility data were obtained by the Faraday method using a Cahn D 200 torsion balance (Bruker) at 1.5 Tesla. X-ray diffraction data were collected on a Bruker Platform (Bruker-AXS SMART APEX). Structures were solved by Direct and Patterson methods using SHELXTL program library. 4 Supporting Information for X-ray data are Available: Tables of crystallographic data collection and refinement parameters, position and thermal parameters, and bond distances and angles for complex 1 and 2 (PDF, CIF). This material have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC for (1) and CCDC for (2). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44) ; e- mail: deposit@ ccdc.cam.ac.uk). Preparation of mer-methyl-(phenyl-2-thiolato-c,s)tris(trimethylphosphine)cobalt(iii) (1): Benzylphenylsulfide (301 mg, 1.50 mmol) in 50 ml of diethylether was combined at - 70 C with [CoMe(PMe 3 ) 4 ] (570 mg, 1.50 mmol) in 50 ml of diethylether. After warm up and further stirring for 30 min at 20 C all volatiles were removed from the mixture in vacuo, and the solid residue was extracted with 80 ml of pentane. From the solution 25 mg, orange thin crystal plates were obtained at 4 C which proved suitable for X-ray diffraction. Upon cooling to - 27 C a second fraction of 1 was collected and combined with the first. Yield 105 mg S2
3 (17%); m.p C. 1 H-NMR for 1 (500 MHz, [D 8 ]THF, 300 K) : δ = (dt, 3 J P,H = 9.3 Hz, 3 J P,H = 8.5 Hz 3H, Co CH 3 ); 1.16 (t', 2 J P,H + 4 J P,H = 6.3 Hz, 18H, PCH 3 ); 1.34 (d, 2 J P,H = 6.6 Hz, 9H, PCH 3 ); 6.03 (d, 3 J H,H = 6.9 Hz, 1H, Ar H); 6.54 (t, 3 J H,H = 6.6 Hz, 1H, Ar H); 6.65 (t, 3 J H,H = 6.0 Hz, 1H, Ar H); 6.89 (s(br), 1H, Ar H) C NMR (125 MHz, [D 8 ]THF, 300 K, ppm): δ = (m, Co-CH 3 ); 15.2 (dt', 1 J P,C + 3 J P,C = 13.5 Hz, 3 J P,C = 3.1 Hz, PCH 3 ); 17.2 (td', 1 J P,C + 3 J P,C = 18.7 Hz, 3 J P,C = 2.9 Hz, PCH 3 ); (s, CH); (s, CH); (d, 3 J P,C = 8.3 Hz, CH); (s, CH); (s, C-S); (m, Co-C).- 31 P NMR (202 MHz, [D 8 ]THF, 300 K, ppm): δ = 17.8 (m(br), 2P, PCH 3 ); (m(br), 1P, PCH 3 ). - Anal calc. for C 16 H 34 CoP 3 S, (410.3): calcd. C 46.83, H 8.35, P 22.64; found C 47.06, H 7.67, P GC-MS Detection: From the reaction of 1 with stoichiometric amounts benzylphenylsulfide, the volatiles were removed in vacuo after 3 h and collected in a 100 ml flask. The collected volatiles were investigated by using a sample of 1.0 μl. GCMS (EI) spectra were recorded using a Hewlett-Packard HP 5890 series II instrument with a DB-5 capillary column ( mm 0.25 μm, Agilent) and a Finnigan MAT-95 mass detector (Thermo) set to scan from 40 to 450 m/z at a rate of 1.5 scans/s. The oven temperature program was as follows: initial temperature 40 C, ramp at 20 C/min to 250 C, hold for 10 min. GC-MS peak assignments: toluene at retention time 5.7 min, molecular peak (EI) at m/z 92; at retention time 19.1 min, molecular peak (EI) at m/z 180 (unknown byproduct). Preparation of mer-methyl-(naphthyl-8-thiolato-c,s)tris(trimethylphosphine)cobalt(iii) (2): Benzylnaphthylsulfide (456 mg, 1.82 mmol) in 50 ml of THF was combined at - 70 C with [CoMe(PMe 3 ) 4 ] (690 mg, 1.82 mmol) in 50 ml of THF. After warm up and further S3
4 stirring for 16 h at 20 C all volatiles were removed from the mixture in vacuo, and the solid residue was extracted with 80 ml of diethylether. From the solution orange rhombic crystals were obtained at -27 C which proved suitable for X-ray diffraction. Yield 621 mg (74%); m.p C. 1 H-NMR for 2 (500 MHz, [D 8 ]THF, 300 K): δ = (dt, 3 J P,H = 8.8 Hz, 3 J P,H = 7.6 Hz, 3H, Co CH 3 ); 0.80 (t', 2 J P,H + 4 J P,H = 7.1 Hz, 18H, PCH 3 ); 1.45 (d, 2 J P,H = 6.7 Hz, 9H, PCH 3 ); 6.84 (t, 3 J H,H = 7.5 Hz, 1H, Ar H); 6.98 (tt, 3 J H,H = 8.0 Hz, 3 J H,H = 7.8 Hz, 2H, Ar H); 7.12 (td, 3 J H,H = 7.7 Hz, 4 J H,H = 1.5 Hz, 1H, Ar H); 7.16 (dd, 3 J H,H = 7.2 Hz, 4 J H,H = 0.7 Hz, 1H, Ar H); 7.20 (dt, 3 J H,H = 7.2 Hz, 4 J P,H = 3.5 Hz, 1H, Ar H).- 13 C NMR (125 MHz, [D 8 ]THF, 300 K, ppm): δ = (m, Co-CH 3 ); 16.9 (dt', 1 J P,C + 3 J P,C = 13.7 Hz, 3 J P,C = 2.5 Hz, PCH 3 ); 19.3 (d, 1 J P,C = 18.7 Hz, PCH 3 ); (s, CH); (t, 5 J P,C = 3.8 Hz, CH); (s, CH); (s, CH); (d, 3 J P,C = 10.0 Hz, CH); (t, 4 J P,C = 5.0 Hz, CH); (s, C); (s, C); (d, 3 J P,C = 8.8 Hz, C); (m, Co-C).- 31 P NMR (202 MHz, [D 8 ]THF, 300 K, ppm): δ : (m(br), 1P, PCH 3 ); 4.3 (m(br), 2P, PCH 3 ) P NMR (202 MHz, [D 8 ]THF, 203 K, ppm): δ = 9.1 (t, 2 J P,P = 37.6, 1P, PCH 3 ), 15.5 (d, 2 J P,P = 37.6 Hz, 2P, PCH 3 ). - Anal calc. for C 20 H 36 CoP 3 S, (460.4): calcd. C 52.17, H 7.88, P 20.18; found C 52.10, H 8.28, P References 1 W. Strohmeier, Chem. Ber. 1955, 88, W. Wolfsberger, H. Schmidbaur, Syn. React. Inorg. Metal-Org. Chem. 1974, 4, Klein, H.-F.; Karsch, H. H. Chem. Ber. 1975, 108, G. M. Sheldrick. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. S4
5 Crystallographic Section Table 1. Crystal data and structure refinement for 1. Identification code 1 Empirical formula C16 H34 Co P3 S Formula weight Temperature 293(2) K Wavelength Å Crystal system Orthorhombic Space group Pcab Unit cell dimensions a = (11) Å α= (8). b = (12) Å β= (8). c = (3) Å γ = (7). Volume (7) Å 3 Z 8 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) 1744 Crystal size 0.32 x 0.25 x 0.10 mm 3 Theta range for data collection 4.25 to Index ranges -14<=h<=15, -15<=k<=15, -33<=l<=33 Reflections collected Independent reflections 4321 [R(int) = ] Completeness to theta = % Absorption correction None Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 4321 / 0 / 190 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole and e.å -3 S5
6 Table 2. Atomic coordinates ( x 10 4 ) and equivalent isotropic displacement parameters (Å 2 x 10 3 ) for 1. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor. x y z U(eq) C(1) 1888(3) 259(3) 9005(1) 46(1) C(2) 1252(3) -255(2) 8648(1) 44(1) C(3) 136(3) -320(3) 8680(1) 55(1) C(4) -380(3) 155(3) 9088(2) 66(1) C(5) 228(3) 683(3) 9430(2) 70(1) C(6) 1356(3) 732(3) 9397(1) 60(1) C(7) 4266(3) 736(3) 9296(1) 59(1) C(8) 4677(3) -1898(3) 9468(2) 74(1) C(9) 2643(4) -2516(3) 9098(2) 111(2) C(10) 2818(5) -1092(5) 9890(2) 126(2) C(11) 4843(3) -1932(3) 8161(2) 68(1) C(12) 4659(4) -104(3) 7623(1) 71(1) C(13) 6138(3) -192(3) 8421(2) 81(1) C(14) 2417(3) 1783(3) 7891(1) 70(1) C(15) 2657(3) 2610(3) 8845(2) 72(1) C(16) 4492(3) 2301(3) 8277(2) 67(1) P(1) 3383(1) -1339(1) 9277(1) 56(1) P(2) 3243(1) 1609(1) 8443(1) 44(1) P(3) 4743(1) -528(1) 8272(1) 46(1) S(1) 2135(1) -774(1) 8195(1) 48(1) Co(1) 3377(1) 12(1) 8758(1) 35(1) S6
7 Table 3. Bond lengths [Å] and angles [ ] for 1. C(1)-C(6) 1.382(5) C(1)-C(2) 1.405(5) C(1)-Co(1) 1.977(3) C(2)-C(3) 1.380(5) C(2)-S(1) 1.765(3) C(3)-C(4) 1.409(6) C(3)-H(3) C(4)-C(5) 1.367(6) C(4)-H(4) C(5)-C(6) 1.393(5) C(5)-H(5) C(6)-H(6) C(7)-Co(1) 2.040(3) C(7)-H(7A) C(7)-H(7B) C(7)-H(7C) C(8)-P(1) 1.822(4) C(8)-H(8A) C(8)-H(8B) C(8)-H(8C) C(9)-P(1) 1.822(4) C(9)-H(9A) C(9)-H(9B) C(9)-H(9C) C(10)-P(1) 1.823(4) C(10)-H(10A) C(10)-H(10B) C(10)-H(10C) C(11)-P(3) 1.822(4) C(11)-H(11A) C(11)-H(11B) C(11)-H(11C) C(12)-P(3) 1.835(4) C(12)-H(12A) C(12)-H(12B) C(12)-H(12C) C(13)-P(3) 1.816(4) S7
8 C(13)-H(13A) C(13)-H(13B) C(13)-H(13C) C(14)-P(2) 1.818(4) C(14)-H(14A) C(14)-H(14B) C(14)-H(14C) C(15)-P(2) 1.824(4) C(15)-H(15A) C(15)-H(15B) C(15)-H(15C) C(16)-P(2) 1.829(4) C(16)-H(16A) C(16)-H(16B) C(16)-H(16C) P(1)-Co(1) (10) P(2)-Co(1) (9) P(3)-Co(1) (9) S(1)-Co(1) (9) C(6)-C(1)-C(2) 117.7(3) C(6)-C(1)-Co(1) 140.1(3) C(2)-C(1)-Co(1) 102.2(2) C(3)-C(2)-C(1) 122.8(3) C(3)-C(2)-S(1) 129.4(3) C(1)-C(2)-S(1) 107.8(3) C(2)-C(3)-C(4) 118.1(4) C(2)-C(3)-H(3) C(4)-C(3)-H(3) C(5)-C(4)-C(3) 119.6(4) C(5)-C(4)-H(4) C(3)-C(4)-H(4) C(4)-C(5)-C(6) 121.7(4) C(4)-C(5)-H(5) C(6)-C(5)-H(5) C(1)-C(6)-C(5) 120.1(4) C(1)-C(6)-H(6) C(5)-C(6)-H(6) Co(1)-C(7)-H(7A) S8
9 Co(1)-C(7)-H(7B) H(7A)-C(7)-H(7B) Co(1)-C(7)-H(7C) H(7A)-C(7)-H(7C) H(7B)-C(7)-H(7C) P(1)-C(8)-H(8A) P(1)-C(8)-H(8B) H(8A)-C(8)-H(8B) P(1)-C(8)-H(8C) H(8A)-C(8)-H(8C) H(8B)-C(8)-H(8C) P(1)-C(9)-H(9A) P(1)-C(9)-H(9B) H(9A)-C(9)-H(9B) P(1)-C(9)-H(9C) H(9A)-C(9)-H(9C) H(9B)-C(9)-H(9C) P(1)-C(10)-H(10A) P(1)-C(10)-H(10B) H(10A)-C(10)-H(10B) P(1)-C(10)-H(10C) H(10A)-C(10)-H(10C) H(10B)-C(10)-H(10C) P(3)-C(11)-H(11A) P(3)-C(11)-H(11B) H(11A)-C(11)-H(11B) P(3)-C(11)-H(11C) H(11A)-C(11)-H(11C) H(11B)-C(11)-H(11C) P(3)-C(12)-H(12A) P(3)-C(12)-H(12B) H(12A)-C(12)-H(12B) P(3)-C(12)-H(12C) H(12A)-C(12)-H(12C) H(12B)-C(12)-H(12C) P(3)-C(13)-H(13A) P(3)-C(13)-H(13B) H(13A)-C(13)-H(13B) P(3)-C(13)-H(13C) S9
10 H(13A)-C(13)-H(13C) H(13B)-C(13)-H(13C) P(2)-C(14)-H(14A) P(2)-C(14)-H(14B) H(14A)-C(14)-H(14B) P(2)-C(14)-H(14C) H(14A)-C(14)-H(14C) H(14B)-C(14)-H(14C) P(2)-C(15)-H(15A) P(2)-C(15)-H(15B) H(15A)-C(15)-H(15B) P(2)-C(15)-H(15C) H(15A)-C(15)-H(15C) H(15B)-C(15)-H(15C) P(2)-C(16)-H(16A) P(2)-C(16)-H(16B) H(16A)-C(16)-H(16B) P(2)-C(16)-H(16C) H(16A)-C(16)-H(16C) H(16B)-C(16)-H(16C) C(8)-P(1)-C(9) 100.9(2) C(8)-P(1)-C(10) 98.3(2) C(9)-P(1)-C(10) 101.1(3) C(8)-P(1)-Co(1) (14) C(9)-P(1)-Co(1) (16) C(10)-P(1)-Co(1) (17) C(14)-P(2)-C(15) (19) C(14)-P(2)-C(16) (19) C(15)-P(2)-C(16) 98.09(19) C(14)-P(2)-Co(1) (13) C(15)-P(2)-Co(1) (14) C(16)-P(2)-Co(1) (13) C(13)-P(3)-C(11) (19) C(13)-P(3)-C(12) 101.3(2) C(11)-P(3)-C(12) 97.87(18) C(13)-P(3)-Co(1) (16) C(11)-P(3)-Co(1) (13) C(12)-P(3)-Co(1) (13) C(2)-S(1)-Co(1) 78.23(12) S10
11 C(1)-Co(1)-C(7) (15) C(1)-Co(1)-P(2) 85.08(10) C(7)-Co(1)-P(2) 84.08(10) C(1)-Co(1)-P(1) 85.08(10) C(7)-Co(1)-P(1) 84.34(11) P(2)-Co(1)-P(1) (4) C(1)-Co(1)-P(3) (10) C(7)-Co(1)-P(3) 98.80(11) P(2)-Co(1)-P(3) 96.49(4) P(1)-Co(1)-P(3) 97.35(4) C(1)-Co(1)-S(1) 71.69(10) C(7)-Co(1)-S(1) (11) P(2)-Co(1)-S(1) 95.42(3) P(1)-Co(1)-S(1) 94.44(4) P(3)-Co(1)-S(1) 88.78(3) Symmetry transformations used to generate equivalent atoms: S11
12 Table 4. Anisotropic displacement parameters (Å 2 x 10 3 )for 1. The anisotropic displacement factor exponent takes the form: -2π 2 [ h 2 a* 2 U h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 C(1) 41(2) 50(2) 46(2) 2(2) 5(2) 3(1) C(2) 47(2) 42(2) 43(2) 10(1) 3(2) 2(1) C(3) 44(2) 50(2) 72(2) 16(2) 1(2) -1(2) C(4) 45(2) 59(2) 95(3) 20(2) 18(2) 7(2) C(5) 68(3) 69(2) 72(3) 4(2) 29(2) 13(2) C(6) 60(2) 66(2) 55(2) -9(2) 10(2) 2(2) C(7) 67(2) 61(2) 48(2) -8(2) -12(2) 0(2) C(8) 73(3) 75(3) 73(3) 21(2) -15(2) 12(2) C(9) 85(3) 81(3) 166(5) 64(3) -33(3) -38(3) C(10) 133(5) 171(6) 74(3) 66(3) 46(3) 68(4) C(11) 75(3) 52(2) 78(3) -13(2) 7(2) 7(2) C(12) 87(3) 77(3) 48(2) -3(2) 26(2) 10(2) C(13) 43(2) 85(3) 114(4) -16(3) 8(2) -4(2) C(14) 76(3) 68(2) 67(3) 16(2) -18(2) 2(2) C(15) 69(3) 47(2) 100(3) -8(2) 6(2) 10(2) C(16) 64(2) 53(2) 83(3) 10(2) 9(2) -13(2) P(1) 48(1) 63(1) 57(1) 25(1) 0(1) 0(1) P(2) 43(1) 38(1) 51(1) 3(1) -1(1) -1(1) P(3) 40(1) 46(1) 52(1) -3(1) 6(1) 1(1) S(1) 44(1) 52(1) 49(1) -7(1) -4(1) -5(1) Co(1) 34(1) 38(1) 32(1) -1(1) 0(1) -1(1) S12
13 Table 5. Hydrogen coordinates ( x 10 4 ) and isotropic displacement parameters (Å 2 x 10 3 ) for 1. x y z U(eq) H(3) H(4) H(5) H(6) H(7A) H(7B) H(7C) H(8A) H(8B) H(8C) H(9A) H(9B) H(9C) H(10A) H(10B) H(10C) H(11A) H(11B) H(11C) H(12A) H(12B) H(12C) H(13A) H(13B) H(13C) H(14A) H(14B) H(14C) H(15A) H(15B) H(15C) H(16A) H(16B) S13
14 H(16C) Perspective view of 1 with thermal ellipsoids at the 30 % probability level. C14 C16 C15 P2 C12 C4 C3 C2 S1 Co1 P3 C5 C6 C1 C7 C11 C13 C9 P1 C10 C8 Figure 1. Molecular structure of 1. S14
15 Table 1. Crystal data and structure refinement for 2. Identification code 2: Empirical formula C20 H36 Co P3 S Formula weight Temperature Wavelength Crystal system Space group 293(2) K Å monoclinic P21/c Unit cell dimensions a = (14) Å α= 90. b = (8) Å β= (12). c = (4) Å γ = 90. Volume (5) Å 3 Z 4 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) 976 Crystal size 0.27 x 0.25 x 0.08 mm 3 Theta range for data collection 1.53 to Index ranges -11<=h<=11, -11<=k<=11, -33<=l<=33 Reflections collected Independent reflections 4882 [R(int) = ] Completeness to theta = % Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 4882 / 0 / 370 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole and e.å -3 S15
16 Table 2. Atomic coordinates ( x 10 4 ) and equivalent isotropic displacement parameters (Å 2 x 10 3 ) for 2. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor. x y z U(eq) C(1) 4547(5) 7961(4) 4581(1) 28(1) C(2) 2485(4) 6120(4) 4017(1) 21(1) C(3) 2307(4) 5505(4) 4489(1) 29(1) C(4) 1308(5) 4402(4) 4573(1) 33(1) C(5) 460(4) 3864(4) 4195(1) 29(1) C(6) 593(4) 4420(4) 3699(1) 25(1) C(7) -272(4) 3901(4) 3291(1) 30(1) C(8) -179(4) 4525(4) 2822(1) 33(1) C(9) 776(4) 5654(4) 2738(1) 26(1) C(10) 1685(4) 6161(4) 3123(1) 22(1) C(11) 1592(4) 5558(4) 3615(1) 21(1) C(12) 5764(6) 5273(5) 3168(2) 42(1) C(13) 5386(6) 4482(5) 4161(2) 45(1) C(14) 7367(5) 6619(6) 3963(2) 42(1) C(15) 6435(5) 10499(5) 3942(2) 39(1) C(16) 6310(5) 9087(6) 2999(2) 41(1) C(17) 4184(6) 11020(5) 3237(2) 41(1) C(18) 722(5) 9799(5) 3622(2) 36(1) C(19) 2488(5) 10746(5) 4451(2) 37(1) C(20) 685(5) 8392(5) 4541(2) 35(1) Co(1) 3799(1) 7730(1) 3855(1) 19(1) P(1) 5528(1) 6096(1) 3785(1) 26(1) P(2) 5156(1) 9534(1) 3534(1) 28(1) P(3) 1990(1) 9126(1) 4099(1) 25(1) S(1) 2951(1) 7514(1) 3038(1) 24(1) S16
17 Table 3. Bond lengths [Å] and angles [ ] for 2. C(1)-Co(1) 2.051(3) C(2)-C(3) 1.393(5) C(2)-C(11) 1.441(4) C(2)-Co(1) 1.991(4) C(3)-C(4) 1.408(6) C(4)-C(5) 1.363(5) C(5)-C(6) 1.426(5) C(6)-C(7) 1.424(5) C(6)-C(11) 1.432(5) C(7)-C(8) 1.381(5) C(8)-C(9) 1.401(5) C(9)-C(10) 1.399(5) C(10)-C(11) 1.429(4) C(10)-S(1) 1.745(4) C(12)-P(1) 1.827(4) C(13)-P(1) 1.825(5) C(14)-P(1) 1.823(5) C(15)-P(2) 1.833(4) C(16)-P(2) 1.834(4) C(17)-P(2) 1.836(5) C(18)-P(3) 1.829(4) C(19)-P(3) 1.846(4) C(20)-P(3) 1.826(4) Co(1)-P(3) (11) Co(1)-P(1) (11) Co(1)-P(2) (11) Co(1)-S(1) (9) C(3)-C(2)-C(11) 116.2(3) S17
18 C(3)-C(2)-Co(1) 126.1(3) C(11)-C(2)-Co(1) 117.7(2) C(2)-C(3)-C(4) 122.3(3) C(5)-C(4)-C(3) 121.9(3) C(4)-C(5)-C(6) 119.4(4) C(7)-C(6)-C(5) 121.6(3) C(7)-C(6)-C(11) 119.6(3) C(5)-C(6)-C(11) 118.7(3) C(8)-C(7)-C(6) 120.0(4) C(7)-C(8)-C(9) 120.9(3) C(10)-C(9)-C(8) 120.9(3) C(9)-C(10)-C(11) 119.5(3) C(9)-C(10)-S(1) 123.4(3) C(11)-C(10)-S(1) 117.1(2) C(10)-C(11)-C(6) 119.0(3) C(10)-C(11)-C(2) 119.4(3) C(6)-C(11)-C(2) 121.6(3) C(2)-Co(1)-C(1) 94.39(15) C(2)-Co(1)-P(3) 85.84(10) C(1)-Co(1)-P(3) 84.77(12) C(2)-Co(1)-P(1) 85.93(10) C(1)-Co(1)-P(1) 85.38(12) P(3)-Co(1)-P(1) (4) C(2)-Co(1)-P(2) (9) C(1)-Co(1)-P(2) 95.33(13) P(3)-Co(1)-P(2) 94.86(4) P(1)-Co(1)-P(2) 95.02(4) C(2)-Co(1)-S(1) 86.29(9) C(1)-Co(1)-S(1) (12) P(3)-Co(1)-S(1) 94.51(4) P(1)-Co(1)-S(1) 95.44(4) S18
19 P(2)-Co(1)-S(1) 83.99(4) C(14)-P(1)-C(13) 98.9(2) C(14)-P(1)-C(12) 103.2(2) C(13)-P(1)-C(12) 98.5(2) C(14)-P(1)-Co(1) (17) C(13)-P(1)-Co(1) (17) C(12)-P(1)-Co(1) (16) C(15)-P(2)-C(16) 101.4(2) C(15)-P(2)-C(17) 100.6(2) C(16)-P(2)-C(17) 97.2(2) C(15)-P(2)-Co(1) (15) C(16)-P(2)-Co(1) (16) C(17)-P(2)-Co(1) (17) C(20)-P(3)-C(18) 99.0(2) C(20)-P(3)-C(19) 98.5(2) C(18)-P(3)-C(19) 102.6(2) C(20)-P(3)-Co(1) (16) C(18)-P(3)-Co(1) (15) C(19)-P(3)-Co(1) (16) C(10)-S(1)-Co(1) 99.34(11) Symmetry transformations used to generate equivalent atoms: S19
20 Table 4. Anisotropic displacement parameters (Å 2 x 10 3 )for 2. The anisotropic displacement factor exponent takes the form: -2π 2 [ h 2 a* 2 U h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 C(1) 34(2) 28(2) 22(2) -3(1) -4(2) 6(2) C(2) 26(2) 18(2) 21(2) -1(1) -2(1) 4(2) C(3) 38(2) 26(2) 24(2) 2(1) -1(2) -4(2) C(4) 48(2) 28(2) 24(2) 6(1) 1(2) 3(2) C(5) 35(2) 21(2) 32(2) 5(1) 4(2) -3(2) C(6) 29(2) 19(2) 27(2) -2(1) 2(1) 5(2) C(7) 29(2) 22(2) 38(2) -3(2) -1(2) -5(2) C(8) 35(2) 36(2) 29(2) -9(2) -7(2) -3(2) C(9) 29(2) 28(2) 22(2) -3(1) -3(1) 0(2) C(10) 24(2) 21(2) 19(1) -4(1) 1(1) 2(2) C(11) 26(2) 19(2) 17(1) -1(1) 0(1) 2(2) C(12) 51(3) 45(3) 30(2) -10(2) -3(2) 16(2) C(13) 61(3) 38(3) 36(2) 3(2) -6(2) 19(2) C(14) 41(3) 45(3) 40(2) -9(2) -8(2) 11(2) C(15) 38(3) 39(3) 41(2) 2(2) -3(2) -10(2) C(16) 40(3) 50(3) 32(2) 6(2) 9(2) -9(2) C(17) 48(3) 35(2) 38(2) 12(2) -1(2) -7(2) C(18) 36(2) 38(3) 33(2) -1(2) -4(2) 4(2) C(19) 43(3) 33(2) 36(2) -6(2) 0(2) 7(2) C(20) 34(2) 41(3) 30(2) -4(2) 8(2) 6(2) Co(1) 24(1) 20(1) 14(1) 0(1) -1(1) 1(1) P(1) 31(1) 28(1) 20(1) -3(1) -3(1) 8(1) P(2) 29(1) 30(1) 25(1) 3(1) 0(1) -6(1) P(3) 27(1) 26(1) 21(1) -3(1) 0(1) 3(1) S(1) 29(1) 27(1) 16(1) 2(1) -2(1) -1(1) S20
21 Table 5. Hydrogen coordinates ( x 10 4 ) and isotropic displacement parameters (Å 2 x 10 3 ) for 2. x y z U(eq) H(8) 5210(60) 8790(60) 4600(20) 77(17) H(10) 3700(50) 8010(50) 4791(17) 42(12) H(13) 5110(50) 7190(50) 4721(17) 52(14) H(11) 2880(40) 5860(40) 4761(14) 26(10) H(28) 1160(50) 3980(50) 4893(17) 53(13) H(1) -250(40) 3140(40) 4234(13) 26(10) H(4) -970(40) 3100(50) 3363(15) 38(11) H(9) -840(40) 4130(50) 2563(16) 49(13) H(18) 890(40) 6140(40) 2428(16) 41(11) H(15) 4850(40) 4860(40) 3066(14) 30(11) H(34) 6210(50) 5980(60) 2920(20) 74(17) H(35) 6680(50) 4590(50) 3191(17) 58(14) H(22) 6410(50) 3970(50) 4140(15) 46(12) H(24) 4250(50) 3940(50) 4061(16) 50(13) H(31) 5300(60) 4670(60) 4490(20) 86(19) H(7) 8090(60) 5790(60) 3973(18) 69(16) H(20) 7620(60) 7370(60) 3760(20) 63(16) H(30) 7320(50) 7050(60) 4250(20) 60(15) H(6) 5940(50) 11040(50) 4167(18) 55(14) H(12) 7240(60) 9870(60) 4099(19) 69(16) H(26) 7060(50) 11100(50) 3727(17) 49(13) H(23) 6680(50) 9930(50) 2848(17) 50(13) H(32) 7170(50) 8580(50) 3094(16) 43(13) H(36) 5750(50) 8570(50) 2737(18) 56(14) H(16) 3440(50) 10670(50) 2991(16) 44(12) S21
22 H(21) 3590(40) 11570(50) 3467(16) 39(12) H(33) 4820(50) 11650(50) 3116(17) 47(13) H(3) 290(40) 8990(40) 3478(14) 28(10) H(5) -50(50) 10390(50) 3783(16) 47(13) H(14) 1210(40) 10360(50) 3346(16) 39(11) H(17) 3000(60) 10440(60) 4720(20) 86(19) H(19) 3100(40) 11320(50) 4262(16) 40(12) H(29) 1450(60) 11260(60) 4562(19) 75(16) H(2) -20(50) 9060(50) 4602(15) 43(12) H(25) 1310(50) 8100(60) 4870(20) 74(16) H(27) 170(50) 7540(50) 4426(18) 57(15) S22
23 Table 6. Torsion angles [ ] for 2. C(11)-C(2)-C(3)-C(4) -0.3(5) Co(1)-C(2)-C(3)-C(4) 177.5(3) C(2)-C(3)-C(4)-C(5) 0.4(6) C(3)-C(4)-C(5)-C(6) 0.6(6) C(4)-C(5)-C(6)-C(7) (4) C(4)-C(5)-C(6)-C(11) -1.6(5) C(5)-C(6)-C(7)-C(8) 175.9(4) C(11)-C(6)-C(7)-C(8) -2.1(5) C(6)-C(7)-C(8)-C(9) 1.1(6) C(7)-C(8)-C(9)-C(10) 1.4(6) C(8)-C(9)-C(10)-C(11) -2.7(5) C(8)-C(9)-C(10)-S(1) 177.4(3) C(9)-C(10)-C(11)-C(6) 1.6(5) S(1)-C(10)-C(11)-C(6) (2) C(9)-C(10)-C(11)-C(2) (3) S(1)-C(10)-C(11)-C(2) 2.5(4) C(7)-C(6)-C(11)-C(10) 0.8(5) C(5)-C(6)-C(11)-C(10) (3) C(7)-C(6)-C(11)-C(2) 179.8(3) C(5)-C(6)-C(11)-C(2) 1.7(5) C(3)-C(2)-C(11)-C(10) 178.3(3) Co(1)-C(2)-C(11)-C(10) 0.3(4) C(3)-C(2)-C(11)-C(6) -0.7(5) Co(1)-C(2)-C(11)-C(6) (3) C(3)-C(2)-Co(1)-C(1) -0.6(3) C(11)-C(2)-Co(1)-C(1) 177.2(3) C(3)-C(2)-Co(1)-P(3) -85.0(3) C(11)-C(2)-Co(1)-P(3) 92.8(3) C(3)-C(2)-Co(1)-P(1) 84.4(3) S23
24 C(11)-C(2)-Co(1)-P(1) -97.8(3) C(3)-C(2)-Co(1)-P(2) (4) C(11)-C(2)-Co(1)-P(2) -1.8(8) C(3)-C(2)-Co(1)-S(1) (3) C(11)-C(2)-Co(1)-S(1) -2.1(2) C(2)-Co(1)-P(1)-C(14) (2) C(1)-Co(1)-P(1)-C(14) -52.7(2) P(3)-Co(1)-P(1)-C(14) -95.4(3) P(2)-Co(1)-P(1)-C(14) 42.24(19) S(1)-Co(1)-P(1)-C(14) (19) C(2)-Co(1)-P(1)-C(13) -29.2(2) C(1)-Co(1)-P(1)-C(13) 65.6(2) P(3)-Co(1)-P(1)-C(13) 22.9(3) P(2)-Co(1)-P(1)-C(13) (18) S(1)-Co(1)-P(1)-C(13) (18) C(2)-Co(1)-P(1)-C(12) 88.8(2) C(1)-Co(1)-P(1)-C(12) (2) P(3)-Co(1)-P(1)-C(12) 141.0(3) P(2)-Co(1)-P(1)-C(12) -81.5(2) S(1)-Co(1)-P(1)-C(12) 3.0(2) C(2)-Co(1)-P(2)-C(15) (6) C(1)-Co(1)-P(2)-C(15) 2.9(2) P(3)-Co(1)-P(2)-C(15) 88.1(2) P(1)-Co(1)-P(2)-C(15) -82.9(2) S(1)-Co(1)-P(2)-C(15) (2) C(2)-Co(1)-P(2)-C(16) -55.4(6) C(1)-Co(1)-P(2)-C(16) 125.7(2) P(3)-Co(1)-P(2)-C(16) (18) P(1)-Co(1)-P(2)-C(16) 39.85(19) S(1)-Co(1)-P(2)-C(16) (18) C(2)-Co(1)-P(2)-C(17) 59.2(6) S24
25 C(1)-Co(1)-P(2)-C(17) (2) P(3)-Co(1)-P(2)-C(17) (18) P(1)-Co(1)-P(2)-C(17) (18) S(1)-Co(1)-P(2)-C(17) 59.49(18) C(2)-Co(1)-P(3)-C(20) 25.05(18) C(1)-Co(1)-P(3)-C(20) -69.8(2) P(1)-Co(1)-P(3)-C(20) -27.1(3) P(2)-Co(1)-P(3)-C(20) (16) S(1)-Co(1)-P(3)-C(20) (16) C(2)-Co(1)-P(3)-C(18) -94.1(2) C(1)-Co(1)-P(3)-C(18) 171.1(2) P(1)-Co(1)-P(3)-C(18) (2) P(2)-Co(1)-P(3)-C(18) 76.17(18) S(1)-Co(1)-P(3)-C(18) -8.17(18) C(2)-Co(1)-P(3)-C(19) (19) C(1)-Co(1)-P(3)-C(19) 47.3(2) P(1)-Co(1)-P(3)-C(19) 90.0(2) P(2)-Co(1)-P(3)-C(19) (17) S(1)-Co(1)-P(3)-C(19) (17) C(9)-C(10)-S(1)-Co(1) 176.5(3) C(11)-C(10)-S(1)-Co(1) -3.5(3) C(2)-Co(1)-S(1)-C(10) 2.72(15) C(1)-Co(1)-S(1)-C(10) -129(7) P(3)-Co(1)-S(1)-C(10) (12) P(1)-Co(1)-S(1)-C(10) 88.27(12) P(2)-Co(1)-S(1)-C(10) (12) Symmetry transformations used to generate equivalent atoms: S25
26 Perspective view of 2 with thermal ellipsoids at the 30 % probability level. C20 C4 C5 C18 C6 C7 C19 P3 C3 C8 C2 C11 C9 C1 Co1 S1 C10 C17 C13 C15 P2 C14 P1 C12 C16 Figure 2. Molecular structure of 2. S26
Supporting Information
Supporting Information Vinylogous elimination/heck coupling/allylation domino reactions: access to 2- substituted 2,3-dihydrobenzofurans and indolines Jianguo Yang, *, Hanjie Mo, Xiuxiu Jin, Dongdong Cao,
Διαβάστε περισσότεραElectronic Supplementary Information (ESI)
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) Cyclopentadienyl iron dicarbonyl (CpFe(CO) 2 ) derivatives
Διαβάστε περισσότεραCycloaddition of Homochiral Dihydroimidazoles: A 1,3-Dipolar Cycloaddition Route to Optically Active Pyrrolo[1,2-a]imidazoles
X-Ray crystallographic data tables for paper: Supplementary Material (ESI) for Organic & Biomolecular Chemistry Cycloaddition of Homochiral Dihydroimidazoles: A 1,3-Dipolar Cycloaddition Route to Optically
Διαβάστε περισσότεραIV. ANHANG 179. Anhang 178
Anhang 178 IV. ANHANG 179 1. Röntgenstrukturanalysen (Tabellen) 179 1.1. Diastereomer A (Diplomarbeit) 179 1.2. Diastereomer B (Diplomarbeit) 186 1.3. Aldoladdukt 5A 193 1.4. Aldoladdukt 13A 200 1.5. Aldoladdukt
Διαβάστε περισσότεραEnantioselective Synthesis of the Anti-inflammatory Agent ( )-Acanthoic Acid
Enantioselective Synthesis of the Anti-inflammatory Agent ( )-Acanthoic Acid Taotao Ling, a Chinmay Chowdhury, a Bryan A. Kramer, a Binh G. Vong, a Michael A. Palladino b and Emmanuel A. Theodorakis a
Διαβάστε περισσότεραSupporting Information. Research Center for Marine Drugs, Department of Pharmacy, State Key Laboratory
Supporting Information Dysiherbols A C and Dysideanone E, Cytotoxic and NF-κB Inhibitory Tetracyclic Meroterpenes from a Dysidea sp. Marine Sponge Wei-Hua Jiao,, Guo-Hua Shi,, Ting-Ting Xu,, Guo-Dong Chen,
Διαβάστε περισσότεραchlorostibine Iou-Sheng Ke and François P. Gabbai Department of Chemistry, Texas A&M University, College Station, TX
σ-donor/acceptor confused ligands: The case of a chlorostibine Iou-Sheng Ke and François P. Gabbai Department of Chemistry, Texas A&M University, College Station, TX 77843-3255. *To whom correspondence
Διαβάστε περισσότεραEnantioselective 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 περισσότεραNickel and Platinum PCP Pincer Complexes Incorporating an Acyclic Diaminoalkyl Central Moiety Connecting Imidazole or Pyrazole Rings
ickel and Platinum PCP Pincer Complexes Incorporating an Acyclic Diaminoalkyl Central Moiety Connecting Imidazole or Pyrazole Rings Braulio M. Puerta Lombardi, Rudy M. Braun, Chris Gendy, Chia Yun Chang,
Διαβάστε περισσότεραPatrycja Miszczyk, Dorota Wieczorek, Joanna Gałęzowska, Błażej Dziuk, Joanna Wietrzyk and Ewa Chmielewska. 1. Spectroscopic Data.
; doi:10.3390/molecules22020254 S1 of S23 Supplementary Materials: Reaction of 3-Amino-1,2,4-Triazole with Diethyl Phosphite and Triethyl Orthoformate: Acid-Base Properties and Antiosteoporotic Activities
Διαβάστε περισσότεραPhoto-Induced Self-Assembly of Pt(II)-Linked Rings and Cages via the Photolabilization of a Pt(II) Pyridine Bond
Photo-Induced Self-Assembly of Pt(II)-Linked Rings and Cages via the Photolabilization of a Pt(II) Pyridine Bond Ken-ichi Yamashita, Kei-ichi Sato, Masaki Kawano and Makoto Fujita* Contents; Figure S1.
Διαβάστε περισσότεραSupporting Information for. Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds
Supporting Information for Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds Zhongxue Fang, a Yongquan Ning, a Pengbing Mi, a Peiqiu Liao, a Xihe Bi* a,b a Department of Chemistry,
Διαβάστε περισσότεραSupporting Information File 2. Crystallographic data of syn-bis-quinoxaline, 16c CH 3 CO 2 C 2 H 5 ;
Supporting Information File 2 Crystallographic data of syn-bis-quinoxaline, 16c CH 3 CO 2 C 2 H 5 ; Preparation, structures and host guest chemistry of fluorinated syn-bisquinoxaline molecular tweezers
Διαβάστε περισσότεραSUPPORTING INFORMATION. Pyramidanes: The Covalent Form of the Ionic Compounds
SUPPORTING INFORMATION Pyramidanes: The Covalent Form of the Ionic Compounds Vladimir Ya. Lee, 1 * Olga A. Gapurenko, 2 Yuki Ito, 1 Takahiko Meguro, 1 Haruka Sugasawa, 1 Akira Sekiguchi, 1 *, Ruslan M.
Διαβάστε περισσότεραSupporting Information
One-Pot, Three-Component Assembly of Indoloquinolines: Total Synthesis of Isocryptolepine Alexander V. Aksenov,* Dmitrii A. Aksenov, Naila A. Orazova, Nicolai A. Aksenov, Georgii D. Griaznov, Annelise
Διαβάστε περισσότεραSupplementary Material
Supplementary Material Synthesis of bis-oxathiaaza[3.3.3]propellanes via nucleophilic addition of (1,ω-alkanediyl)bis(N'-organylthioureas) on dicyanomethylene-1,3-indanedione Alaa A. Hassan, a * Kamal
Διαβάστε περισσότεραSUPPORTING INFORMATION. Diastereoselective synthesis of nitroso acetals from (S,E)- -aminated
SUPPORTING INFORMATION for Diastereoselective synthesis of nitroso acetals from (S,E)- -aminated nitroalkenes via multicomponent [4 + 2]/[3 + 2] cycloadditions promoted by LiCl or LiClO 4 Leandro Lara
Διαβάστε περισσότεραMultifunctinality and Crystal Dynamics of Highly Stable Porous Metal-Organic Framework [Zn 4 O(NTB) 2 ]
Supporting Information Multifunctinality and Crystal Dynamics of Highly Stable Porous Metal-Organic Framework [Zn 4 O(NTB) 2 ] Eun Young Lee, Seung Yeon Jang, and Myunghyun Paik Suh* School of Chemistry,
Διαβάστε περισσότεραElectronic Supplementary Information (ESI)
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) CPh 3 as a functional group in P-heterocyclic
Διαβάστε περισσότεραSupporting Information. for
Supporting Information for A general synthetic route to [Cu(X)(NHC)] (NHC = N- heterocyclic carbene, X =Cl, Br, I) complexes Orlando Santoro, Alba Collado, Alexandra M. Z. Slawin, Steven P. Nolan and Catherine
Διαβάστε περισσότεραSupporting 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 περισσότεραSUPPLEMENTARY MATERIAL. A Facile and Convenient Approach for the Synthesis of Novel Sesamol-Oxazine and Quinoline- Oxazine Hybrids
10.1071/CH17272_AC CSIRO 2017 Australian Journal of Chemistry 2017, 70(12), 1285-1290 SUPPLEMENTARY MATERIAL A Facile and Convenient Approach for the Synthesis of Novel Sesamol-Oxazine and Quinoline- Oxazine
Διαβάστε περισσότεραSupporting Information. A catalyst-free multicomponent domino sequence for the. diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-
Supporting Information for A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3- (arylamino)allyl]chromen-4-ones Pitchaimani Prasanna 1, Pethaiah
Διαβάστε περισσότεραA 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 περισσότεραSupporting information for
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting information for Palladium-Catalyzed Benzothieno[2,3-b]indole Formation via Dehydrative-Dehydrogenative
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Supporting Information Abnormal N-Heterocyclic Carbene Based Nickel Complex for Catalytic
Διαβάστε περισσότεραSynthesis, Characterization, and Computational Study of Three-Coordinate SNS-Copper(I) Complexes Based on Bis-Thione Precursors
For Synthesis, Characterization, and Computational Study of Three-Coordinate SNS-Copper(I) Complexes Based on Bis-Thione Precursors John R. Miecznikowski a *; Matthew A. Lynn b ; Jerry P. Jasinski c ;
Διαβάστε περισσότεραSupplementary Material
Supplementary Material Efficient, mild synthesis of - unsubstituted 1,2,3- triazoles from methanolysis of 1-sulfonyl-1,2,3-triazoles Janeth Rodríguez-Florencio, Diego Martínez-tero, Marco A. García-Eleno,
Διαβάστε περισσότεραStereochemistry and mechanistic insight in the [2 k +2 i +2 i ] annulations of ketenes and imines
Stereochemistry and mechanistic insight in the [2 k +2 i +2 i ] annulations of ketenes and imines Zhanhui Yang, Wei He, Baoxiang Cheng and Jiaxi Xu* State Key Laboratory of Chemical Resource Engineering,
Διαβάστε περισσότεραNH-Type of chiral Ni(II) complexes of glycine Schiff base: design, structural evaluation, reactivity and synthetic applications
Supporting Information NH-Type of chiral Ni(II) complexes of glycine Schiff base: design, structural evaluation, reactivity and synthetic applications Mackenzie Bergagnini, a Kazunobu Fukushi, b Jianlin
Διαβάστε περισσότεραMetal-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 περισσότεραSupporting Information. Palladium Complexes with Bulky Diphosphine. Synthesis of (Bio-) Adipic Acid from Pentenoic. Acid Mixtures.
Supporting Information Palladium Complexes with Bulky Diphosphine Ligands as Highly Selective Catalysts for the Synthesis of (Bio-) Adipic Acid from Pentenoic Acid Mixtures. Choon Heng Low, James D. Nobbs,*
Διαβάστε περισσότεραC H Activation of Cp* Ligand Coordinated to Ruthenium. Center: Synthesis and Reactivity of a Thiolate-Bridged
Supporting Information C H Activation of Cp* Ligand Coordinated to Ruthenium Center: Synthesis and Reactivity of a Thiolate-Bridged Diruthenium Complex Featuring Fulvene-like Cp* Ligand Xiaoxiao Ji, Dawei
Διαβάστε περισσότεραTable of Contents 1 Supplementary Data MCD
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2017 Supporting Information for Magnetic circular dichroism and density functional theory
Διαβάστε περισσότεραSupplementary Information. Living Ring-Opening Polymerization of Lactones by N-Heterocyclic Olefin/Al(C 6 F 5 ) 3
Supplementary Information Living Ring-Opening Polymerization of Lactones by N-Heterocyclic Olefin/Al(C 6 F 5 ) 3 Lewis Pairs: Structures of Intermediates, Kinetics, and Mechanism Qianyi Wang, Wuchao Zhao,
Διαβάστε περισσότεραElectronic supplementary information (ESI) Bodipy functionalized ortho-carborane dyads for low-energy photosensitization
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Electronic supplementary information (ESI) Bodipy functionalized ortho-carborane dyads
Διαβάστε περισσότεραSupporting Information
Supporting Information Gold-catalyzed Cycloisomerization of 1,6-Diyne-4-en-3-ols to form Naphthyl Ketone Derivatives. Jian-Jou Lian and Rai-Shung Liu* Department of Chemistry, National Tsing-Hua University,
Διαβάστε περισσότεραPyrrolo[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 περισσότεραANNEXE 2 : SPECTRES DE RÉSONANCE MAGNÉTIQUE NUCLÉAIRE
ANNEXE 2 : SPECTRES DE RÉSONANCE MAGNÉTIQUE NUCLÉAIRE 175 4-Oxopentyl acetate (1-9) 27.56 17.91 63.49 39.76 29.86 22.66 2.82 2. 1.97 2.91 2.96 2.9 4. 3.98 3.96 2.47 2.44 2.42 2.7 1.95 1.86 1.84 1.82 1.79
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Supporting Information Domino reaction of cyclic sulfamidate imines with
Διαβάστε περισσότεραPractical Pd(II)-catalyzed C H Alkylation with Epoxides: One-step Syntheses of 3,4-Dihydroisocoumarins
Practical Pd(II)-catalyzed C H Alkylation with Epoxides: One-step Syntheses of 3,4-Dihydroisocoumarins Guolin Cheng, Tuan-Jie Li, and Jin-Quan Yu* Department of Chemistry, The Scripps Research Institute,
Διαβάστε περισσότεραSupporting 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 περισσότεραCobalt-Catalyzed Selective Synthesis of Isoquinolines Using Picolinamide as a Traceless Directing Group
Supporting Information Cobalt-Catalyzed Selective Synthesis of Isoquinolines Using Picolinamide as a Traceless Directing Group Changsheng Kuai, Lianhui Wang, Bobin Li, Zhenhui Yang, Xiuling Cui* Engineering
Διαβάστε περισσότεραSynthesis and effects of oxadiazole derivatives on tyrosinase activity and SK-MEL-28 malignant melanoma cells
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 06 Synthesis and effects of oxadiazole derivatives on tyrosinase activity and human SK-MEL-8 malignant
Διαβάστε περισσότεραCopper-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 περισσότεραCopper-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 περισσότεραSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008
Supporting Information Copyright Wiley-VC Verlag Gmb & Co. KGaA, 69451 Weinheim, 2008 Copper Complexes of Mono- and Ditopic [(Methylthio)methyl]borates: Missing Links and Linked Systems En Route to Copper
Διαβάστε περισσότεραSupporting Information. Pd(0)-Catalyzed Decarboxylative Coupling and Tandem C H Arylation/Decarboxylation for the. Synthesis of Heteroaromatic Biaryls
Supporting Information Pd()-Catalyzed Decarboxylative Coupling and Tandem C H Arylation/Decarboxylation for the Synthesis of Heteroaromatic Biaryls Debkumar andi, Yang-Ming Jhou, Jhen-Yi Lee, Bing-Chiuan
Διαβάστε περισσότεραThe 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 περισσότεραElectronic 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 περισσότεραPalladium-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 περισσότεραNitric oxide (NO) reactivity studies on mononuclear Iron(II) complexes supported by a tetradentate Schiff base Ligand
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Nitric oxide (NO) reactivity studies on mononuclear Iron(II) complexes supported by a tetradentate
Διαβάστε περισσότεραSupporting Information
Supporting Information Transition-metal-free Ring Expansion Reactions of Indene-1,3-dione: Synthesis of Functionalized Benzoannulated Seven-Membered Ring Compounds Qiyi Yao, Lingkai Kong, Mengdan Wang,
Διαβάστε περισσότεραCollege of Life Science, Dalian Nationalities University, Dalian , PR China.
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 2018 Postsynthetic modification
Διαβάστε περισσότεραSupporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of. 1,2,3-Triazole Synthesis
Supporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of α-diazoketones with Various Amines: A Strategy for Catalytic Wolff 1,2,3-Triazole Synthesis Zikun Wang, a Xihe
Διαβάστε περισσότεραSupporting 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 περισσότεραHeavier chalcogenone complexes of bismuth(iii)trihalides: Potential catalysts for acylative cleavage of cyclic ethers. Supporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Heavier chalcogenone complexes of bismuth(iii)trihalides: Potential catalysts for acylative
Διαβάστε περισσότεραTunable Ligand Emission of Napthylsalophen Triple-Decker Dinuclear Lanthanide (III) Sandwich Complexes
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2017 Supplemental Information Tunable Ligand Emission of Napthylsalophen Triple-Decker Dinuclear
Διαβάστε περισσότεραE-H (E = B, Si, C) Bond Activation by Tuning Structural and Electronic Properties of Phosphenium Cations
E-H (E = B, Si, C) Bond Activation by Tuning Structural and Electronic Properties of Phosphenium Cations Nemanja Đorđević, Rakesh Ganguly, Milena Petković, and Dragoslav Vidović Email: drasko.vidovic@monash.edu
Διαβάστε περισσότεραDirect 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 περισσότεραSupporting 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 περισσότεραSupporting 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 περισσότεραSupplementary information
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supplementary information Hybrids of acylated homoserine lactone and nitric
Διαβάστε περισσότεραSupporting Information for
Supporting Information for An atom-economic route to densely functionalized thiophenes via base-catalyzed rearrangement of 5-propargyl-2H-thiopyran-4(3H)-ones Chunlin Tang a, Jian Qin b, Xingqi Li *a a
Διαβάστε περισσότεραSynthesis of New Heteroscorpionate Iridium(I) and Iridium(III) Complexes
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2015 ELECTRONIC SUPPORTING INFORMATION For Synthesis of New Heteroscorpionate Iridium(I)
Διαβάστε περισσότεραTable S1. Summary of data collections and structure refinements for crystals 1Rb-1h, 1Rb-2h, and 1Rb-4h.
Supporting Information [NH 3 CH 3 ] [In SbS 9 SH]: A novel methylamine-directed indium thioantimonate with Rb + ion-exchange property Kai-Yao Wang a,b, Mei-Ling Feng a, Jian-Rong Li a and Xiao-Ying Huang
Διαβάστε περισσότεραExperimental. Crystal data
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Terephthalic acid 2,2 0 -dimethyl-1,1 0 - (butane-1,4-diyl)dibenzimidazole (2/3) Hui Jiang and Xian-Wu Dong* Department
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2017 Supporting Information Phosphorescent Pt(II) complexes bearing a monoanionic C^N^N luminophore
Διαβάστε περισσότεραSupporting 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 περισσότεραSynthesis 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 περισσότεραSupporting Information. Generation Response. Physics & Chemistry of CAS, 40-1 South Beijing Road, Urumqi , China. China , USA
Supporting Information Pb 3 B 6 O 11 F 2 : A First Noncentrocentric Lead Fluoroborate with Large Second Harmonic Generation Response Hongyi Li, a Hongping Wu, a * Xin Su, a Hongwei Yu, a,b Shilie Pan,
Διαβάστε περισσότεραTitle N-H versus C-H Activation of a Pyrrole Imine at {Cp*Ir}: A Computational and Experimental Study
Supporting Information for: Title N-H versus C-H Activation of a Pyrrole Imine at {Cp*Ir}: A Computational and Experimental Study David L. Davies,* a Steven M. A. Donald, b Omar Al-Duaij, a John Fawcett,
Διαβάστε περισσότεραSupporting 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 περισσότεραSupporting 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 περισσότεραSupporting 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 περισσότεραFused Bis-Benzothiadiazoles as Electron Acceptors
Fused Bis-Benzothiadiazoles as Electron Acceptors Debin Xia, a,b Xiao-Ye Wang, b Xin Guo, c Martin Baumgarten,*,b Mengmeng Li, b and Klaus Müllen*,b a MIIT Key Laboratory of ritical Materials Technology
Διαβάστε περισσότεραMulti odd-even effects on cell parameters, melting. points, and optical properties of chiral crystal solids. based on S-naproxen
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2015 Supplementary Information Multi odd-even effects on cell parameters, melting points, and optical
Διαβάστε περισσότεραSupporting Information for Substituent Effects on the Properties of Borafluorenes
Supporting Information for Substituent Effects on the Properties of Borafluorenes Mallory F. Smith, S. Joel Cassidy, Ian A. Adams, Monica Vasiliu, Deidra L. Gerlach, David Dixon*, Paul A. Rupar* Department
Διαβάστε περισσότεραSupporting 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 περισσότεραFree 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 περισσότεραSupporting Information
Supporting Information rganocatalytic Enantioselective Formal [4+2] Cycloaddition of Enones with Cyclic N-Sulfonylies and Methylene Chromene for Chiral Spirocyclic Compounds Jie Fei, Qingqing Qian, Xiaohua
Διαβάστε περισσότεραSupporting Information
Supporting Information 1,3,5-Triazapentadienes by Nucleophilic Addition to 1,3- and 1,4-Dinitriles - Sterically Constrained Examples by Incorporation into Cyclic Peripheries: Synthesis, Aggregation and
Διαβάστε περισσότεραIodine-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 περισσότεραSupporting information. An unusual bifunctional Tb-MOF for highly sensing of Ba 2+ ions and remarkable selectivities of CO 2 /N 2 and CO 2 /CH 4
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A. This journal is The Royal Society of Chemistry 2015 Supporting information An unusual bifunctional Tb-MOF for highly sensing
Διαβάστε περισσότεραSUPPLEMENTARY 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 περισσότεραTriclinic, P1 a = (2) Å b = (3) Å c = (4) Å = (1) = (1) = (1) Data collection.
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Benzyl N 0 -(4,6-dimethoxy-2-methyl-3- phenyl-1h-indol-7-ylmethylene)- hydrazinecarbodithioate Hamid Khaldei,
Διαβάστε περισσότεραControlling Growth of Molecular Crystal Aggregates with Distinct Linear and Nonlinear Optical Properties
Supporting Information Controlling Growth of Molecular Crystal Aggregates with Distinct Linear and Nonlinear Optical Properties Yusen Luo,,,# Chunqing Yuan,,# Jialiang Xu*, Yongjun Li*, Huibiao Liu, Sergey
Διαβάστε περισσότεραElectronic 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 περισσότεραZebra reaction or the recipe for heterodimeric zinc complexes synthesis
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 05 Supporting Information Zebra reaction or the recipe for heterodimeric zinc complexes synthesis
Διαβάστε περισσότεραBloco A, Cidade Universitária, Ilha do Fundão, Rio de Janeiro, RJ, Brazil. Contents Pages
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Supporting Information Copper(II) Catalyzed Synthesis of Novel Helical
Διαβάστε περισσότεραRegioselectivity 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 περισσότεραSupporting Information Synthesis of cyclometalated 1,3,5-triphenylpyrazole palladium dimer and its activity towards cross coupling reactions
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 215 Supporting Information Synthesis of cyclometalated 1,3,5-triphenylpyrazole palladium
Διαβάστε περισσότεραand Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol
FeCl 3 6H 2 O-Catalyzed Disproportionation of Allylic Alcohols and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol Jialiang Wang, Wen Huang, Zhengxing Zhang, Xu
Διαβάστε περισσότεραSupporting 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 περισσότεραSite-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 περισσότεραSupporting Information
Supporting Information for Pyrene nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies Artur Jabłoński 1, Yannic Fritz 2, Hans-Achim Wagenknecht 2, Rafał Czerwieniec
Διαβάστε περισσότεραElectronic, Crystal Chemistry, and Nonlinear Optical Property Relationships. or W, and D = P or V)
Electronic, Crystal Chemistry, and Nonlinear Optical Property Relationships in the Dugganite A 3 B 3 CD 2 O 14 Family (A = Sr, Ba or Pb; B = Mg or Zn; C = Te or W, and D = P or V) Hongwei Yu, Joshua Young,
Διαβάστε περισσότεραKey Laboratory of Functional Materials and Devices for Special Environments, Xinjiang Technical
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2016 KPb 2 (PO 3 ) 5 : A Novel Nonlinear Optical Lead Polyphosphate with Short
Διαβάστε περισσότεραSynthetic Control of Excited States in Cyclometalated Ir(III) Complexes using Ancillary Ligands
Synthetic Control of Excited States in Cyclometalated Ir(III) Complexes using Ancillary Ligands Jian Li, (a) Peter I. Djurovich, (a) Bert D. Alleyne, (a) Muhammed Yousufuddin, (a) Nam N. Ho, (a) J. Christopher
Διαβάστε περισσότεραDivergent 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