Coordination addition polymerization and kinetic resolution of methacrylamides by chiral metallocene catalysts

Macromolecules

Volumn 42, Issue 5, 2009, Pages 1462-1471

  Miyake, Garret ^a   Caporaso, Lucia ^b   Cavallo, Luigi ^b   Chen, Eugene Y X ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

^b UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; ADDITION POLYMERIZATION; AZIRIDINE; AZIRIDINE RING; DEGREE OF CONJUGATIONS; DEGREE OF CONTROL; DOUBLE BONDS; ENOLATE INTERMEDIATES; FIRST ORDER KINETICS; HIGHLY STRAINED; INTRAMOLECULAR CONJUGATE ADDITION; KINETIC RESOLUTION; METALLOCENE CATALYST; METHACRYLAMIDE; METHACRYLAMIDES; MONOMER COORDINATION; POLYMERIZATION REACTIVITY; PROPAGATION MECHANISM; RELATIVE ENERGIES; RING OPENING REACTION; STEREOSPECIFIC; THERMAL CROSSLINKING; THERMALLY INDUCED;

AMIDES; CATALYSIS; CATALYSTS; COORDINATION REACTIONS; MONOMERS; ORGANOMETALLICS; POLYMERIZATION; STEREOSELECTIVITY; ZIRCONIUM;

POLYMERS;

EID: 66549120195     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma802697z     Document Type: Article

References (95)

1. Selected recent reference works and reviews: (a) Chen, E. Y.-X.; Rodriguez-Delgado, A. Complexes of Zirconium and Hafnium in Oxidation State IV. In Comprehensive Organometallic Chemistry III; Bochmann, M., Vol. Ed.; Mingos, M. P., Crabtree, R. H., Chief Eds.; Elsevier: Oxford, 2007; Vol. 4,pp759 1004.
2. (b) Cuenca, T. Complexes of Titanium in Oxidation State IV. In Comprehensive Organometallic Chemistry III; Bochmann, M., Vol. Ed.; Mingos, M. P., Crabtree, R. H., Chief Eds.; Elsevier: Oxford, 2007; Vol. 4,pp 323 696.
3. (c) Bochmann, M. Cationic Group 4 Metallocene Complexes and Their Role in Polymerisation Catalysis: the Chemistry of Well Defined Ziegler Catlaysts. J. Chem. Soc., Dalton Trans. 1996, 255-270.
4. (d) Jordan, R. F. Chemistry of Cationic Dicyclopentadienyl Group 4 Metal-Alkyl Complexes. Adv. Organomet. Chem. 1991, 32, 325-387.
5. Selected books, reference works, or journal reviews: (a) Stereoselective Polymerization with Single-Site Catalysts; Baugh, L. S., Canich, J. A. M., Eds.; CRC Press: Boca Raton, FL, 2008.
6. (b) Resconi, L.; Chadwick, J. C.; Cavallo, L. Olefin Polymerizations with Group IV Metal Catalysts. In Comprehensi e Organometallic Chemistry III; Bochmann, M., Vol. Ed.; Mingos, M. P., Crabtree, R. H., Chief Eds.; Elsevier: Oxford, 2007; Vol. 4, pp 1005 1166.
7. (c) Domski, G. J.; Rose, J. M.; Coates, G. W.; Bolig, A. D.; Brookhart, M. Living Alkene Polymerization: New Methods for the Precision Synthesis of Polyolefins. Prog. Polym. Sci. 2007, 32, 30-92.
8. (d) Marks, T.J. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 15288-15354, and contributions therein (issue on "Polymerization Special Feature").
9. (e) Gibson, V.C.; Spitzmesser, S.K. Advances in Non-Metallocene Olefin Polymerization Catalysis. Chem. Rev. 2003, 103, 283-315.
10. (f) Gladysz, J. A. Chem. Rev. 2000, 100, 1167-1681, and contributions therein (issue on "Frontiers in Metal-Catalyzed Polymerization").
11. (g) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Stereospecific Olefin Polymerization. Angew. Chem., Int. Ed. 1995, 34, 1143-1170.
12. Ning, Y.; Chen, E. Y.-X. J. Am. Chem. Soc. 2008, 130, 2463-2465.
13. Mariott, W. R.; Escudé, N. C.; Chen, E. Y.-X. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 2581-2592.
14. Lian, B.; Thomas, C. M.; Navarro, C.; Carpentier, J.-F. Organometallics 2007, 26, 187-195.
15. Ning, Y.; Chen, E. Y.-X. Macromolecules 2006, 39, 7204-7215.
16. Rodriguez-Delgado, A.; Mariott, W. R.; Chen, E. Y.-X. J. Organomet. Chem. 2006, 691, 3490-3497.
17. Rodriguez-Delgado, A.; Chen, E. Y.-X. Macromolecules 2005, 38, 2587-2594.
18. Kostakis, K.; Mourmouris, S.; Kotakis, K.; Nikogeorgos, N.; Pitsikalis, M.; Hadjichristidis, N. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 3305-3314.
19. Ning, Y.; Cooney, M. J.; Chen, E. Y.-X. J. Organomet. Chem. 2005, 690, 6263-6270.
20. Lian, B.; Lehmann, C. W.; Navarro, C.; Carpentier, J.-F. Organometallics 2005, 24, 2466-2472.
21. Bolig, A. D.; Chen, E. Y.-X. J. Am. Chem. Soc. 2004, 126, 4897-4906.
22. Stojcevic, G.; Kim, H.; Taylor, N. J.; Marder, T. B.; Collins, S. Angew. Chem., Int. Ed. 2004, 43, 5523-5526.
23. Strauch, J. W.; Fauré, J.-L.; Bredeau, S.; Wang, C.; Kehr, G.; Fröhlich, R.; Luftmann, H.; Erker, G. J. Am. Chem. Soc. 2004, 126, 2089-2104.
24. Karanikolopoulos, G.; Batis, C.; Pitsikalis, M.; Hadjichristidis, N. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 3761-3774.
25. Ferenz, M.; Bandermann, F.; Sustmann, R.; Sicking, W. Macromol. Chem. Phys. 2004, 205, 1196-1205.
26. Rodriguez-Delgado, A.; Mariott, W. R.; Chen, E. Y.-X. Macromolecules 2004, 37, 3092-3100.
27. Lian, B.; Toupet, L.; Carpentier, J.-F. Chem.sEur. J. 2004, 10, 4301-4307.
28. Jensen, T. R.; Yoon, S. C.; Dash, A. K.; Luo, L.; Marks, T.J. J. Am. Chem. Soc. 2003, 125, 14482-14494.
29. Chen, E. Y.-X.; Cooney, M. J. J. Am. Chem. Soc. 2003, 125, 7150-7151.
30. Mariott, W. R.; Chen, E. Y.-X. J. Am. Chem. Soc. 2003, 125, 15726-15727.
31. Jin, J.; Mariott, W. R.; Chen, E. Y.-X. J. Polym. Chem., Part A: Polym. Chem. 2003, 41, 3132-3142.
32. Batis, C.; Karanikolopoulos, G.; Pitsikalis, M.; Hadjichristidis, N. Macromolecules 2003, 36, 9763-9774.
33. Karanikolopoulos, G.; Batis, C.; Pitsikalis, M.; Hadjichristidis, N. Macromol. Chem. Phys. 2003, 204, 831-840.
34. Bolig, A. D.; Chen, E. Y.-X. J. Am. Chem. Soc. 2002, 124, 5612-5613.
35. Jin, J.; Chen, E. Y.-X. Organometallics 2002, 21, 13-15.
36. Jin, J.; Wilson, D. R.; Chen, E. Y.-X. Chem. Commun. 2002, 708-709.
37. Jin, J.; Chen, E. Y.-X. Macromol. Chem. Phys. 2002, 203, 2329-2333.
38. Bandermann, F.; Ferenz, M.; Sustmann, R.; Sicking, W. Macromol. Symp. 2001, 174, 247-253.
39. Karanikolopoulos, G.; Batis, C.; Pitsikalis, M.; Hadjichristidis, N. Macromolecules 2001, 34, 4697-4705.
40. Bolig, A. D.; Chen, E. Y.-X. J. Am. Chem. Soc. 2001, 123, 7943-7944.
41. Frauenrath, H.; Keul, H.; Höcker, H. Macromolecules 2001, 34, 14-19.
42. Nguyen, H.; Jarvis, A. P.; Lesley, M. J. G.; Kelly, W. M.; Reddy, S. S.; Taylor, N. J.; Collins, S. Macromolecules 2000, 33, 1508-1510.
43. Bandermann, F.; Ferenz, M.; Sustmann, R.; Sicking, W. Macromol. Symp. 2000, 161, 127-134.
44. Cameron, P. A.; Gibson, V.; Graham, A.J. Macromolecules 2000, 33, 4329-4335.
45. Stuhldreier, T.; Keul, H.; Höcker, H. Macromol. Rapid Commun. 2000, 21, 1093-1098.
46. Chen, E. Y.-X.; Metz, M. V.; Li, L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 6287-6305.
47. Shiono, T.; Saito, T.; Saegusa, N.; Hagihara, H.; Ikeda, T.; Deng, H.; Soga, K. Macromol. Chem. Phys. 1998, 199, 1573-1579.
48. Hong, E.; Kim, Y.; Do, Y. Organometallics 1998, 17, 2933-2935.
49. Li, Y.; Ward, D. G.; Reddy, S. S.; Collins, S. Macromolecules 1997, 30, 1875-1883.
50. Deng, H.; Shiono, T.; Soga, K. Macromol. Chem. Phys. 1995, 196, 1971-1980.
51. Deng, H.; Shiono, T.; Soga, K. Macromolecules 1995, 28, 3067-3073.
52. Soga, K.; Deng, H.; Yano, T.; Shiono, T. Macromolecules 1994, 27, 7938-7940.
53. Collins, S.; Ward, D. G.; Suddaby, K. H. Macromolecules 1994, 27, 7222-7224.
54. Collins, S.; Ward, S. G. J. Am. Chem. Soc. 1992, 114, 5460-5462.
55. Lian, B.; Thomas, C. M.; Navarro, C.; Carpentier, J.-F. Macromolecules 2007, 40, 2293-2294.
56. Mariott, W. R.; Rodriguez-Delgado, A.; Chen, E. Y.-X. Macromolecules 2006, 39, 1318-1327.
57. Kostakis, K.; Mourmouris, S.; Pitsikalis, M.; Hadjichristidis, N. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 3337-3348.
58. Deng, H.; Soga, K. Macromolecules 1996, 29, 1847-1848.
59. Miyake, G. M.; Chen, E. Y.-X. Macromolecules 2008, 41, 3405-3416.
60. Miyake, G. M.; Mariott, W. R.; Chen, E. Y.-X. J. Am. Chem. Soc. 2007, 129, 6724-6725.
61. Mariott, W. R.; Chen, E. Y.-X. Macromolecules 2005, 38, 6822-6832.
62. Mariott, W. R.; Chen, E. Y.-X. Macromolecules 2004, 37, 4741-4743.
63. Spaether, W.; Kla, K.; Erker, G.; Zippel, F.; Fröhlich, R. Chem.sEur. J. 1998, 4, 1411-1417.
64. Ning, Y.; Caporaso, L.; Correa, A.; Gustafson, L. O.; Cavallo, L.; Chen, E. Y.-X. Macromolecules 2008, 41, 6910-6919.
65. Caporaso, L.; Cavallo, L. Macromolecules 2008, 41, 3439-3445.
66. Caporaso, L.; Gracia-Budrìa, J.; Cavallo, L. J. Am. Chem. Soc. 2006, 128, 16649-16654.
67. Tomasi, S.; Weiss, H.; Ziegler, T. Organometallics 2007, 26, 2157-2166.
68. Tomasi, S.; Weiss, H.; Ziegler, T. Organometallics 2006, 25, 3619-3630.
69. Hölscher, M.; Keul, H.; Höcker, H. Macromolecules 2002, 35, 8194-8202.
70. Hölscher, M.; Keul, H.; Höcker, H. Chem.-Eur. J. 2001, 7, 5419-5426.
71. Sustmann, R.; Sicking, W.; Bandermann, F.; Ferenz, M. Macromolecules 1999, 32, 4204-4213.
72. Xie, X.; Hogen-Esch, T. E. Macromolecules 1996, 29, 1746-1752.
73. Kodaira, T.; Tanahashi, H.; Hara, K. Polym. J. 1990, 22, 649-659.
74. Okamoto, Y.; Yuki, H. J. Polym. Sci., Polym. Chem. Ed. 1981, 19, 2647-2650.
75. (a) Suzuki, T.; Kusakabe, J.; Ishizone, T. Macromolecules 2008, 41, 1929-1936.
76. (b) Suzuki, T.; Kusakabe, J.; Ishizone, T. Macromol. Symp. 2007, 249 250, 412-416.
77. Christoffers, J.; Schulze, Y.; Pickardt, J. Tetrahedron 2001, 57, 1765-1769.
78. (a) Grossman, R.B.; Doyle, R.A.; Buchwald, S.L. Organometallics 1991, 10, 1501-1505.
79. (b) Collins, S.; Kuntz, B. A.; Taylor, N. J.; Ward, D. G. J. Organomet. Chem. 1988, 342, 21-29.
80. Diamond, G. M.; Jordan, R. F.; Petersen, J. L. J. Am. Chem. Soc. 1996, 118, 8024-8033.
81. LoCoco, M. D.; Jordan, R. F. J. Am. Chem. Soc. 2004, 126, 13918-13919.
82. (a) Carpentier, J.-F.; Maryin, V. P.; Luci, J.; Jordan, R. F. J. Am. Chem. Soc. 2001, 123, 898-909.
83. (b) Stevens, J. C.; Timmers, F. J.; Wilson D. R.; Schmidt, G. F.; Nickias, P. N.; Rosen, R. K.; Knight, G. W.; Lai, S. Eur. Pat. Appl. EP 0 416815 A2, 1991.
84. Chen, Y.-X.; Marks, T. J. Organometallics 1997, 16, 3649-3657.
85. Ueda, M.; Takahashi, M.; Suzuki, T. J. Polym Sci. Polym. Phys. Ed. 1983, 20, 1139-1149.
86. (a) ADF2007, Users's Manual, Theoretical Chemistry; Vrije Universiteit, Amsterdam, 2007.
87. (b) Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2, 41-51.
88. Vosko, S.-H.; Wilk, L.; Nusair, M. Can. J. Phys 1980, 58, 1200-1211.
89. Becke, A. D. Phys. ReV. A 1988, 38, 3098-3100.
90. (a) Perdew, J.P. Phys. Rev. B 1986, 33, 8822-8824.
91. (b) Perdew, J.P. Phys. Rev. B 1986, 34, 7406-7406.
92. (a) Klamt, A.; Schüürmann, G. J. Chem. Soc., Perkin Trans. 1993, 799-805.
93. (b) Pye, C. C.; Ziegler, T. Theor. Chim. Acta 1999, 101, 396-408.
94. Eliel, A. L.; Wilen, S. H.; Mander, L.N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; pp 266 268.
95. The ideal sp3 valence angle of 109.47° is closer to the 60° valence angle of a three-membered ring than the ideal sp2 value of 120°.