A mechanistic investigation on copolymerization of ethylene with polar monomers using a cyclophane-based Pd(II) α-diimine catalyst

Journal of the American Chemical Society

Volumn 131, Issue 34, 2009, Pages 12384-12393

  Popeney, Chris S ^a   Guan, Zhibin ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BLOCKING EFFECT; COMONOMER INCORPORATION; CYCLOPHANES; DIIMINES; EQUILIBRIUM STUDY; EQUIVALENT CONDITION; EXCHANGE RATES; KINETIC BEHAVIOR; KINETIC PLOTS; MECHANISTIC STUDIES; METHYL ACRYLATES; MIGRATORY INSERTION; NMR SPECTROSCOPY; OLEFIN COMPLEXES; POLAR MONOMER; POLYMERIZATION TEMPERATURE; SLOW EQUILIBRATION;

ACRYLIC MONOMERS; APPROXIMATION THEORY; CATALYSIS; CATALYSTS; COPOLYMERIZATION; CYANIDES; EQUILIBRIUM CONSTANTS; ETHYLENE; LIGANDS; MONOMERS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM;

PALLADIUM COMPOUNDS;

ACRYLIC ACID METHYL ESTER; ALKENE; CYCLOPHANE DERIVATIVE; ETHYLENE; IMINE; LIGAND; MONOMER; NITRILE; PALLADIUM; STYRENE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL BINDING; CONTROLLED STUDY; EQUILIBRIUM CONSTANT; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION LINE; TEMPERATURE;

EID: 69349093092     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja904471v     Document Type: Article

References (32)

1. This paper has been adapted in part from the following thesis: Ph.D. Dissertation. University of California at Irvine, CA. Popeney, C. S. 2008.
2. Ittel, S. D.; Johnson, L. K.; Brookhart, M. Chem. Rev. 2000, 100, 1169-1203.
3. Younkin, T. R.; Connor, E. F.; Henderson, J. I.; Friedrich, S. K.; Grubbs, R. H.; Bansleben, D. A. Science 2000, 287, 460-462.
4. Boffa, L. S.; Novak, B. M. Chem. Rev. 2000, 100, 1479-1493.
5. Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283-315.
6. Small, B. L.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 7143-7144.
7. Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414-6415.
8. Johnson, L. K.; Mecking, S.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 267-268.
9. Hicks, F. A.; Brookhart, M. Organometallics 2001, 20, 3217-3219.
10. Drent, E.; van Dijk, R.; van Ginkel, R.; van Oort, B.; Pugh, R. I. Chem. Commun. 2002, 744-745.
11. Luo, S.; Vela, J.; Lief, G. R.; Jordan, R. F. J. Am. Chem. Soc. 2007, 129, 8946-8947.
12. Gottker-Schnetmann, I.; Korthals, B.; Mecking, S. J. Am. Chem. Soc. 2006, 128, 7708-7709.
13. Kochi, T.; Noda, S.; Yoshimura, K.; Nozaki, K. J. Am. Chem. Soc. 2007, 129, 8948-8949.
14. Guironnet, D.; Roesle, P.; Ruenzi, T.; Goettker-Schnettmann, I.; Mecking, S. J. Am. Chem. Soc. 2009, 131, 422-423.
15. Mecking, S.; Johnson, L. K.; Wang, L.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 888-899.
16. Michalak, A.; Ziegler, T. J. Am. Chem. Soc. 2001, 123, 12266-12278.
17. Szabo, M. J.; Jordan, R. F.; Michalak, A.; Piers, W. E.; Weiss, T.; Yang, S.-Y.; Ziegler, T. Organometallics 2004, 23, 5565-5572.
18. Gates, D. P.; Svejda, S. K.; Onate, E.; Killian, C. M.; Johnson, L. K.; White, P. S.; Brookhart, M. Macromolecules 2000, 33, 2320-2334.
19. Tempel, D. J.; Johnson, L. K.; Huff, R. L.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 2000, 122, 6686-6700.
20. Camacho, D. H.; Salo, E. V.; Ziller, J. W.; Guan, Z. Angew. Chem., Int. Ed. 2004, 43, 1821-1825.
21. Camacho, D. H.; Guan, Z. Macromolecules 2005, 38, 2544-2546.
22. Popeney, C. S.; Camacho, D. H.; Guan, Z. J. Am. Chem. Soc. 2007, 129, 10062-10063.
23. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 3rd ed.; John Wiley and Sons, Inc: New York, 2001.
24. Shriver, D. F.; Atkins, P. W. Inorganic Chemistry, 3rd ed.; W. H. Freeman and Company: New York, 1999.
25. Houston, P. L. Chemical Kinetics and Reaction Dynamics; McGraw-Hill: New York, 2001.
26. Eigen, M. Discuss. Faraday Soc. 1954, 17, 194-205.
27. Bracken, D. E.; Baldwin, H. W. Inorg. Chem. 1974, 13, 1325-1329.
28. Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967.
29. Dimitrov, V. S.; Vassilev, N. G. Magn. Reson. Chem. 1995, 33, 739-744.
30. The equilibrium geometry of cyclophane ethylene adduct 4b was generated by the Spartan software package (Wavefunction, Inc., of Irvine, CA). The structure of the methyl chloride complex obtained from X-ray crystallography (ref 20) was imported, the chloride ligand removed, and an ethylene molecule substituted. Semi-empirical calculations (PM3) were performed, which converged to the shown structure regardless of the starting configuration of the olefin (whether in or perpendicular to the metal coordination plane).
31. Shultz, L. H.; Tempel, D. J.; Brookhart, M. J. Am. Chem. Soc. 2001, 123, 11539-11555.
32. Seeman, J. I. Chem. Rev. 1983, 83, 83-134.