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1 SUPPORTING INFORMATION Cis-Selective Ring-Opening Metathesis Polymerization with Ruthenium Catalysts Benjamin K. Keitz, Alexey Fedorov, Robert H. Grubbs* Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California, General Information.... S3 General Polymerization Procedure.... S3 Preparation of Poly-3... S5 Preparation of Poly-4... S7 Preparation of Poly-5... S9 Preparation of Poly-6... S11 Preparation of Poly-7... S13 Preparation of Poly-8... S15 Preparation of Poly-9... S17 Preparation of Poly S19 Preparation of Poly S21 Preparation of Poly S23 Preparation of Poly S25 Preparation of Poly S27 Figure S1. Temperature dependence of cis content of poly-3 prepared from S4 Figure S2. 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-3 prepared with 2 at RT..... S5 Figure S3. 13 C NMR (101 MHz, CDCl 3 ) spectrum of poly-3 prepared with 2 at RT.... S6 Figure S4. HSQC (CDCl 3 ) of poly-3 prepared with 2 at RT.... S6 Figure S5. 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-4 prepared with 2 at RT.... S7 Figure S6. 13 C NMR (101 MHz, CDCl 3 ) spectrum of poly-4 prepared with 2 at RT.... S8 Figure S7. HSQC (CDCl 3 ) of poly-4 prepared with 2 at RT.... S8 Figure S8. 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-5 prepared with 2 at RT.... S9 Figure S9. 13 C NMR (101 MHz, CDCl 3 ) spectrum of poly-5 prepared with 2 at RT.... S10 Figure S10. HSQC (CDCl 3 ) of poly-5 prepared with 2 at RT.... S10 Figure S11. 1 H NMR (400 MHz, d 6 -Acetone) spectrum of poly-6 prepared with 2 at RT.... S11 Figure S C NMR (126 MHz, d 6 -Acetone) spectrum of poly-6 prepared with 1 at RT.... S12 Figure S13. HSQC (d 6 -Acetone) of poly-6 prepared with 1 at RT.... S12 Figure S14. 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-7 prepared with 2 at RT.... S13 Figure S C NMR (101 MHz, CDCl 3 ) spectrum of poly-7 prepared with 2 at RT.... S14 Figure S16. HSQC (CDCl 3 ) of poly-7 prepared with 2 at RT.... S14 Figure S17. 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-8 prepared with 2 at RT.... S15 Figure S C NMR (101 MHz, CDCl 3 ) spectrum of poly-8 prepared with 2 at RT.... S16 Figure S19. HSQC (CDCl 3 ) of poly-8 prepared with 2 at RT.... S16 Figure S20. 1 H NMR (500 MHz, CDCl 3, 50 C) spectrum of poly-9 prepared with S17 Figure S C NMR (126 MHz, CDCl 3, 50 C) spectrum of poly-9 prepared with S18 Figure S22. HSQC (CDCl 3, 50 C) of poly-9 prepared with S18 Figure S23. 1 H NMR (500 MHz, CDCl 3 ) spectrum of poly-10 prepared with S19 Figure S C NMR (126 MHz, CDCl 3 ) spectrum of poly-10 prepared with S20 Figure S25. HSQC (CDCl 3 ) of poly-10 prepared with S20 Figure S26. 1 H NMR (500 MHz, CDCl 3 ) spectrum of poly-11 prepared with S21 Figure S C NMR (126 MHz, CDCl 3 ) spectrum of poly-11 prepared with S22 Figure S28. HSQC (CDCl 3 ) of poly-11 prepared with S22 Figure S29. 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-12 prepared with S23 Figure S C NMR (101 MHz, CDCl 3 ) spectrum of poly-12 prepared with S24 S1
2 Figure S31. HSQC (CDCl 3 ) of poly-12 prepared with S24 Figure S32. 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-13 prepared with S25 Figure S C NMR (101 MHz, CDCl 3 ) spectrum of poly-13 prepared with S26 Figure S34. HSQC (CDCl 3 ) of poly-13 prepared with S26 Figure S35. 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-15 prepared with S27 Figure S C NMR (101 MHz, CDCl 3 ) spectrum of poly-15 prepared with S28 Figure S37. HSQC (CDCl 3 ) of poly-15 prepared with S28 S2
3 General Information. All reactions were carried out in dry glassware under an argon atmosphere using standard Schlenk line techniques or in a Vacuum Atmospheres Glovebox under a nitrogen atmosphere unless otherwise specified. All solvents were purified by passage through solvent purification columns and further degassed with argon. 1 NMR solvents for air-sensitive compounds were dried over CaH 2 and vacuum transferred or distilled into a dry Schlenk flask and subsequently degassed with argon. Commercially available reagents were used as received unless otherwise noted. Compounds 5, 2 6, 3 7, 4 8, 5 9, 6 10, 7 15, 8 and complex 2 9 were synthesized according to the literature procedures, while monomers 3, 4, and 11 were purchased from Sigma Aldrich and used as received. Monomers 12 and 13 were purchased from Sigma Aldrich, distilled, and passed through a plug of neutral alumina prior to use. Standard NMR spectroscopy experiments were conducted on a Varian Inova 400 MHz spectrometer, a Varian 500 MHz spectrometer equipped with an AutoX probe, or a Varian 600 MHz spectrometer equipped with a Triax Probe. Experiments and pulse sequences from Varian s Chempack 4 software were used. Chemical shifts are reported in ppm downfield from Me 4 Si by using the residual solvent peak as an internal standard. Spectra were analyzed and processed using MestReNova Ver Statistical fits were obtained using OriginPro 8.1. Polymer molecular weights were determined by multi-angle light scattering (MALS) gel permeation chromatography (GPC) using a minidawn TREOS light scattering detector, a Viscostar viscometer, and an OptilabRex refractive index detector, all from Wyatt Technology. An Agilent 1200 UV- Vis detector was also present in the detector stack. Absolute molecular weights were determined using dn/dc values calculated by assuming 100% mass recovery of the polymer sample injected into the GPC. No internal standards were used General Polymerization Procedure. In a glovebox, a stock solution of catalyst was prepared from 2 (78 mg, mmol) and THF (1 ml). An aliquot (50 µl, mmol 2) of stock solution was added to a Schlenk flask and diluted with THF (0.5 ml). On a vacuum manifold, a separate Schlenk flask was flame-dried and charged with monomer (0.62 mmol) and THF (2 ml). The monomer solution was degassed via freeze-pump-thaw (3X) (1) Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, (2) Tabor, D.C.; White, F.H.; Collier, L.W.; Evans, S.A. J. Org. Chem. 1983, 48, (3) Alimuniar, A. B.; Blackmore, P. M.; Edwards, J. H.; Feast, W. J.; Wilson, B. Polymer 1986, 27, (4) Story, P. R. J. Org. Chem. 1961, 26, 287. (5) Wittig, G.; Otten, J. Tet. Lett. 1963, 601. (6) Flook, M. M.; Ng, V. W. L.; Schrock, R. R. J. Am. Chem. Soc. 2011, 133, (7) Vera, A. M.; Velásquez, W.; Briceño, A.; Bahsas, A. B.; Valero, B. R.; de Delgado, G. D.; J. Chem. Crystallogr. 2007, 37, 543. (8) Walker, R.; Conrad, R. M.; Grubbs, R. H. Macromolecules 2009, 42, 599. (9) Endo, K.; Grubbs, R. H. J. Am. Chem. Soc. 2011, 133, (10) S3
4 and the catalyst solution was injected via gas-tight syringe under argon at a given temperature. After stirring for 1h, the polymerization was quenched with ethyl vinyl ether (0.1 ml) and, unless otherwise specified, precipitated into vigorously stirred MeOH. The precipitate was collected by vacuum filtration using either a medium or fine porosity frit and dried under vacuum. Figure S1. Temperature dependence of cis content of poly-3 prepared from 1. Conditions were monomer (0.5 mmol) and 1 (0.005 mmol) in THF (2 ml). Cis content was determined by 1 H NMR spectroscopy. For temperatures 0 C, -20 C, and -40 C, (H 2 IMes)Cl 2 Ru(=CH-o- i Pr-Ph) was used as the catalyst. S4
5 poly-3 n Preparation of Poly-3 Poly-3 was prepared according to the general procedure. NMR samples were prepared by stirring poly-3 in CDCl 3 at 50 C for several hours. 1 H and 13 C NMR spectral assignments were consistent with literature reports A B ppm ppm Figure S2. (A) 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-3 prepared with 2 at RT. (B, inset) Olefin region 1 H NMR spectrum of poly-3 prepared with 1 at RT. (11) Al Samak, B.; Amir-Ebrahimi, V.; Corry, D. G.; Hamilton, J. G.; Rigby, S.; Rooney, J. J.; Thompson, J. M. J. Mol. Catal. A: Chem. 2000, 160, 13. S5
6 Figure S3. 13 C NMR (101 MHz, CDCl 3 ) spectrum of poly-3 prepared with 2 at RT. Figure S4. HSQC (CDCl 3 ) of poly-3 prepared with 2 at RT. S6
7 poly-4 n Preparation of Poly-4 Poly-4 was prepared according to the general procedure. NMR samples were prepared by stirring poly-4 in CDCl 3 at 50 C overnight. The polymer never dissolved completely. 1 H and 13 C NMR spectral assignments were consistent with literature reports. 11 A B ppm ppm Figure S5. (A) 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-4 prepared with 2 at RT. (B, inset) Olefin region of 1 H NMR spectrum of poly-4 prepared with 1 at RT. S7
8 Figure S6. 13 C NMR (101 MHz, CDCl 3 ) spectrum of poly-4 prepared with 2 at RT. Figure S7. HSQC (CDCl 3 ) of poly-4 prepared with 2 at RT. S8
9 MeO 2 C CO 2 Me poly-5 n Preparation of Poly-5 Poly-5 was prepared according to the general procedure. NMR samples were prepared by dissolving poly-5 in CDCl 3. 1 H and 13 C NMR spectral assignments were consistent with literature reports. 12 A B ppm ppm Figure S8. (A) 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-5 prepared with 2 at RT. (B, inset) Olefin region of 1 H NMR spectrum of poly-5 prepared with 1 at RT. (12) McConville, D. H.; Wolf, J. R.; Schrock, R. R. J. Am. Chem. Soc. 1993, 115, S9
10 Figure S9. 13 C NMR (101 MHz, CDCl 3 ) spectrum of poly-5 prepared with 2 at RT. Figure S10. HSQC (CDCl 3 ) of poly-5 prepared with 2 at RT. S10
11 F 3 C CF 3 poly-6 n Preparation of Poly-6 Poly-6 was prepared according to the general procedure but isolated via precipitation into hexanes after stirring overnight. NMR Samples were prepared by dissolving poly-6 in d 6 -Acetone. 1 H and 13 C NMR spectral assignments were consistent with literature reports Figure S11. (A) 1 H NMR (400 MHz, d 6 -Acetone) spectrum of poly-6 prepared with 2 at RT. (B, inset) Olefin region of 1 H NMR spectrum of poly-6 prepared with 1 at RT. S11
12 Figure S C NMR (126 MHz, d 6 -Acetone) spectrum of poly-6 prepared with 1 at RT. Figure S13. HSQC (d 6 -Acetone) of poly-6 prepared with 1 at RT. S12
13 O t Bu poly-7 n Preparation of Poly-7 Poly-7 was prepared according to the general procedure. NMR samples were prepared by stirring poly-7 in CDCl 3 at 50 C until complete dissolution. 1 H and 13 C NMR spectral assignments were consistent with literature reports Figure S14. (A) 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-7 prepared with 2 at RT. (B, inset) Olefin region of 1 H NMR spectrum of poly-7 prepared with 1 at RT. (13) Amir-Ebrahimi, V.; Corry, D. A.; Hamilton, J. G.; Thompson, J. M.; Rooney, J. J. Macromolecules 2000, 33, 717. S13
14 Figure S C NMR (101 MHz, CDCl 3 ) spectrum of poly-7 prepared with 2 at RT. Figure S16. HSQC (CDCl 3 ) of poly-7 prepared with 2 at RT. S14
15 Cl poly-8 n Preparation of Poly-8 Poly-8 was prepared according to the general procedure. NMR samples were prepared by stirring poly-8 in CDCl 3 at RT until complete dissolution. 1 H-NMR (500 MHz, with 2): 5.71, 5.69 (2s, H cis+trans ), 5.62 (br s, H trans ), 5.40 (t-like, H cis ), 3.92 (br m), 3.66 (br m), 3.47 (br s). 13 C-NMR (125 MHz): , , , , , , , , , 69.02, 68.70, 57.70, 57.46, 53.48, Figure S17. (A) 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-8 prepared with 2 at RT. (B, inset) Olefin region of 1 H NMR spectrum of poly-8 prepared with 1 at RT. S15
16 Figure S C NMR (101 MHz, CDCl 3 ) spectrum of poly-8 prepared with 2 at RT. f1 (ppm) trans-4 cis-4 Figure S19. HSQC (CDCl 3 ) of poly-8 prepared with 2 at RT. S16
17 MeO 2 C CO 2 Me poly-9 n Preparation of Poly-9 Poly-9 was prepared according to the general procedure. NMR samples were prepared by stirring poly-9 in CDCl 3 at 50 C until complete dissolution. 1 H and 13 C NMR spectral assignments were consistent with literature reports Figure S20. (A) 1 H NMR (500 MHz, CDCl 3, 50 C) spectrum of poly-9 prepared with 2. (B, inset) Olefin region of 1 H NMR spectrum of poly-9 prepared with 1 at RT. S17
18 Figure S C NMR (126 MHz, CDCl 3, 50 C) spectrum of poly-9 prepared with 2. 1-trans 1-cis Figure S22. HSQC (CDCl 3, 50 C) of poly-9 prepared with 2. S18
19 Preparation of Poly-10 Poly-10 was prepared according to the general procedure. NMR samples were prepared by stirring poly-10 in CDCl 3 until complete dissolution. 1 H and 13 C NMR spectral assignments were consistent with literature reports Figure S23. (A) 1 H NMR (500 MHz, CDCl 3 ) spectrum of poly-10 prepared with 2. (B, inset) Olefin region of 1 H NMR spectrum of poly-10 prepared with 1 at RT. S19
20 f1 (ppm) f1 (ppm) f1 (ppm) Figure S C NMR (126 MHz, CDCl 3 ) spectrum of poly-10 prepared with cis-2 70 trans f1 (ppm) trans-1 cis f2 (ppm) Figure S25. HSQC (CDCl 3 ) of poly-10 prepared with 1. S20
21 O poly-11 n Preparation of Poly-11 Poly-11 was prepared according to the general procedure. NMR samples were prepared by stirring poly-11 in CDCl 3 until complete dissolution. 1 H and 13 C NMR spectral assignments were consistent with literature reports Figure S26. (A) 1 H NMR (500 MHz, CDCl 3 ) spectrum of poly-11 prepared with 2. (B, inset) Olefin region of 1 H NMR spectrum of poly-11 prepared with 1 at RT. S21
22 ppm Figure S C NMR (126 MHz, CDCl 3 ) spectrum of poly-11 prepared with cis-2 trans f1 (ppm) 120 trans-1 cis f2 (ppm) Figure S28. HSQC (CDCl 3 ) of poly-11 prepared with 1. S22
23 Preparation of Poly-12 In a glovebox, a 4 ml vial was charged with 2 (1.4 mg, mmol) and THF (100 L). Monomer 12 (59 L, 0.44 mmol) was added and the vial was sealed and stirred for 3 days, after which it was removed from the glovebox and quenched with ethyl vinyl ether. Methanol was added to induce precipitation and the resulting suspension was stirred overnight. The precipitate was collected on a fine frit and washed with methanol to give poly-12 (9 mg, 19%). 1 H and 13 C NMR spectra were consistent with literature reports ppm Figure S29. 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-12 prepared with 2. (14) Flook, M. M.; Jiang, A. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, S23
24 Figure S30. (A) 13 C NMR (101 MHz, CDCl 3 ) spectrum of poly-12 prepared with 2. (B, inset) Alkyl region of 13 C NMR spectrum of poly-12 prepared with 1 at RT cis 2-trans f1 (ppm) 1-cis + 1-trans f2 (ppm) Figure S31. HSQC (CDCl 3 ) of poly-12 prepared with 2. S24
25 Preparation of Poly-13 In a glovebox, a Schlenk flask was charged with 2 (7.3 mg, mmol) and THF (0.5 ml). The flask was sealed and removed from the glovebox. A separate Schlenk flask was charged with 13 (0.3 ml, 3.4 mmol) and degassed by freeze-pump-thaw (3X). The catalyst solution was added to the monomer and the resulting solution was stirred for 5 h after which the reaction was quenched with ethyl vinyl ether. Methanol was added and the resulting precipitate was collected by vacuum filtration to give poly-13 (55 mg, 24%). 1 H and 13 C NMR spectra were consistent with literature reports Figure S32. 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-13 prepared with 2. (15) Trzaka, S. T.; Lee, L. B. W.; Register, R. A. Marcomolecules 2000, 33, S25
26 Figure S33. (A) 13 C NMR (101 MHz, CDCl 3 ) spectrum of poly-13 prepared with 2. (B, inset) Alkyl region of 13 C NMR spectrum of poly-13 prepared with 1 at RT. cis-2 trans f1 (ppm) f2 (ppm) Figure S34. HSQC (CDCl 3 ) of poly-13 prepared with 2. S26
27 Preparation of Poly-15 All glassware used for handling and polymerizing trans-cyclootene (15) was silanized with 10% Cl 2 SiMe 2 in toluene according to the literature procedure. 8 In a glovebox, a Schlenk flask was charged with 2 (4.6 mg, mmol) and THF (0.25 ml), after which the flask was sealed and removed from the glovebox. A separate side-arm flask (silanized) was dried and charged with 15 (80 mg, mmol) and THF (0.5 ml). The catalyst solution was added to the monomer solution via syringe and the resulting gel was vigorously stirred for 1 h, at which point the reaction was quenched with ethyl vinyl ether. Methanol was added to induce precipitation and the resulting suspension was stirred overnight. The precipitate was collected by vacuum filtration and dried to give poly-15 (36 mg, 44%). 1 H and 13 C NMR spectra were consistent with literature reports Figure S35. 1 H NMR (400 MHz, CDCl 3 ) spectrum of poly-15 prepared with 2. (16) Ҫetinkaya, S.; Karabulut, S.; Düz, B.; Ïmamglu, Y. Appl. Organomet. Chem. 2005, 19, 347. S27
28 Figure S36. (A) 13 C NMR (101 MHz, CDCl 3 ) spectrum of poly-15 prepared with 2. (B, inset) Alkyl region of 13 C NMR spectrum of poly-15 prepared with 1 at RT trans-1 cis f2 (ppm) cis-2 trans f1 (ppm) f1 (ppm) f2 (ppm) Figure S37. HSQC (CDCl 3 ) of poly-15 prepared with 2. S28
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