Lanthanide borohydride complexes supported by diaminobis(phenoxide) ligands for the polymerization of ε-caprolactone and L- and rac-lactide

Inorganic Chemistry

Volumn 44, Issue 24, 2005, Pages 9046-9055

  Bonnet, Fanny ^a   Cowley, Andrew R ^a   Mountford, Philip ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; CAPROLACTONE; CHLORIDE; DIAMINE; HEXANOIC ACID DERIVATIVE; LACTIC ACID; LACTONE; LIGAND; POLYMER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; INORGANIC CHEMISTRY; METHODOLOGY; SYNTHESIS;

BOROHYDRIDES; CHEMISTRY, INORGANIC; CHLORIDES; DIAMINES; HEXANOIC ACIDS; LACTIC ACID; LACTONES; LIGANDS; MOLECULAR STRUCTURE; POLYMERS;

EID: 28944441264     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic051316g     Document Type: Article

References (64)

1. Selected reviews on aspects of biodegradable polymers: (a) Okada, M. Prog. Polym. Sci. 2002, 27, 87.
2. (b) Drumright, R. E.; Gruber, P. R.; Henton, D. E. Adv. Mater. 2000, 12, 1841.
3. (c) Chiellini, E.; Solaro, R. Adv. Mater. 1996, 8, 305.
4. Reviews addressing the polymerization of cyclic esters: (a) Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. Chem. Rev. 2004, 104, 6147.
5. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467.
6. (c) Hou, Z.; Wakatsuki, Y. Coord. Chem. Rev. 2002, 231, 1.
7. (d) O'Keefe, B. J.; Hillmyer, M. A.; Tolman, W. B. Dalton Trans. 2001, 2215.
8. (e) Aida, T.; Inoue, S. Acc. Chem. Res. 1996, 29, 39.
9. For leading references concerning main-group initiators, see refs 2a, 2b, 2d, and 2e and the following: (a) Ma, H.; Melillo, G.; Olivia, L.; Spaniol, T. P.; Englert, U.; Okuda, J. Dalton Trans. 2005, 721.
10. (b) Chisholm, M. H.; Patmore, N. J.; P., Z. Z. Chem. Commun. 2005, 127.
11. (c) Nimitsiriwat, N.; Marshall, E. L.; Gibson, V. C.; Elsegood, M. R. J.; Dale, S. H. J. Am. Chem. Soc. 2004, 126, 13598.
12. (d) Hormnirun, P.; Marshall, E. L.; Gibson, V. C.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 2004, 126, 2688.
13. (e) Tang, Z. H.; Chen, X. S.; Pang, X.; Yang, Y. K.; Zhang, X. F.; Jing, X. B. Biomacromolecules 2004, 5, 965.
14. (f) Chisholm, M. H.; Gallucci, J. C.; Phomphrai, K. Inorg. Chem. 2004, 43, 6717.
15. (g) Chisholm, M. H.; Gallucci, J. C.; Phomphrai, K. Inorg. Chem. 2002, 41, 2785.
16. (h) Chisholm, M. H.; Huffman, J. C.; Phomphrai, K. J. Chem. Soc., Dalton Trans. 2001, 222.
17. (i) Chamberlain, B. M.; Cheng, M.; Moore, D. R.; Ovitt, T. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2001, 123, 3229.
18. (j) Cheng, M.; Attygalle, A. B.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 11583.
19. (k) Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 4072.
20. Spassky, N.; Wisniewski, M.; Pluta, C.; LeBorgne, A. Macromol. Chem. Phys. 1996, 197, 2627.
21. For reviews of aspects of non-cyclopentadienyl group 3 and lanthanide chemistry, see: (a) Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283.
22. (b) Piers, W. E.; Emslie, D. J. H. Coord. Chem. Rev. 2002, 233, 131.
23. (c) Mountford, P.; Ward, B. D. Chem. Commun. 2003, 1797 (feature article review).
24. (d) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102, 1851.
25. (e) Marques, N.; Sella, A.; Takats, J. Chem. Rev. 2002, 102, 2137.
26. 2a-d For studies of bis(phenoxide)-supported rare-earth systems of particular relevance to our current work, see: (a) Yao, Y.; Ma, M.; Xu, X.; Zhang, Y.; Shen, Q.; Wong, W.-T. Organometallics 2005, 24, 4014.
27. (b) Ma, H.; Okuda, J. Macromolecules 2005, 38, 2665.
28. (c) Cai, C.-X.; Amgoune, A.; Lehmann, C. W.; Carpentier, J.-F. Chem. Commun. 2004, 330.
29. (d) Kerton, F. M.; Whitwood, A. C.; Willans, C. E. Dalton Trans. 2004, 15, 2237.
30. (e) Ma, H.; Spaniol, T. P.; Okuda, J. Dalton Trans. 2003, 24, 4770.
31. (f) Cai, C.-X.; Toupet, L.; Lehmann, C. W.; Carpentier, J.-F. J. Organomet. Chem. 2003, 683, 44.
32. (g) Yao, Y.; Xu, X.; Zhang, Y.; Shen, Q.; Wong, W.-T. Inorg. Chem. 2005, 44, 5133.
33. Rare-earth borohydride systems in polymerization catalysis: (a) Guillaume, S. M.; Schappacher, M.; Soum, A. Macromolecules 2003, 36, 54.
34. (b) Pallard, I.; Soum, A.; Guillaume, S. M. Macromolecules 2005, 38, 6888.
35. (c) Palard, I.; Soum, A.; Guillaume, S. M. Chem. Eur. J. 2004, 10, 4054.
36. (d) Bonnet, F.; Visseaux, M.; Pereira, A.; Bouyer, F.; Barbier-Baudry, D. Macromol. Rapid Commun. 2004, 25, 873.
37. (e) Bonnet, F.; Visseaux, M.; Barbier-Baudry, D.; Vigier, E.; Kubicki, M. M. Chem. Eur. J. 2004, 10, 2428.
38. (f) Bonnet, F.; Visseaux, M.; Pereira, A.; Barbier-Baudry, D. Macromolecules 2005, 38, 3162.
39. (g) Bonnet, F.; Hillier, A. C.; Collins, A.; Dubberley, S. R.; Mountford, P. Dalton Trans. 2005, 3, 421.
40. Bonnet, F.; Collins, A.; Cowley, A. R.; Mountford, P. Unpublished results.
41. For recent reviews of phenoxide-based Ziegler-Natta-type olefin polymerization catalysts, see ref 4a and the following: (a) Suzuki, Y.; Terao H.; Fujita, T. Bull. Chem. Soc. Jpn. 2003, 76, 1493.
42. (b) Mitani, M.; Saito, J.; Ishii, S.; Nakayama, Y.; Makio, H.; Matsukawa, N.; Matsui, S.; Mohri, J.; Furuyama, R.; Terao, H.; Bando, H.; Tanaka H.; Fujita, T. Chem. Rec. 2004, 4, 137.
43. For rare-earth complexes with tetradentate bis(phenoxide) ligands, see refs 5a-f and the following: (a) Boyd, C. L.; Toupance, T.; Tyrrell, B. R.; Ward, B. D.; Wilson, C. R.; Cowley, A. R.; Mountford, P. Organometallics 2005, 24, 309.
44. (b) O'Shaughnessy, P. N.; Knight, P. D.; Morton, C.; Gillespie, K. M.; Scott, P. Chem. Commun. 2003, 1770.
45. Skinner, M. E. G.; Tyrell, B. R.; Ward, B. D.; Mountford, P. J. Organomet. Chem. 2002, 647, 145.
46. (a) Toupance, T.; Dubberley, S. R.; Rees, N. H.; Tyrrell, B. R.; Mountford, P. Organometallics 2002, 21, 1367.
47. (b) Mirsaidov, U.; Shaimuradov, I. B.; Khikmatov, M. Russ. J. Inorg. Chem. 1986, 5, 753.
48. (c) Bonnet, F.; Visseaux, M.; Barbier-Baudry, D.; Hafid, A.; Vigier, E.; Kubicki, M. M. Inorg. Chem. 2004, 43, 3682.
49. Ephritikhine, M. Chem. Rev. 1997, 97, 2193.
50. Kaltsoyannis, N.; Scott, P. The f Elements; Oxford University Press: Oxford, U.K., 1999.
51. (a) Spassky, N.; Simic, V.; Montaudo, M. S.; Hubert-Pfalzgraf, L. G.; Macromol. Chem. Phys. 2000, 201, 2432.
52. (b) Montaudo, G.; Montaudo, M. S.; Puglisi, C.; Samperi, F.; Spassky, N.; LeBorgne, A.; Wisniewski, Macromolecules 1996, 29, 6461.
53. (c) Baran, J.; Duda, A.; Kowalski, A.; Szymanski, R.; Penczek, S. Macromol. Symp. 1997, 123, 93.
54. (d) Baran, J.; Duda, A.; Kowalski, A.; Szymanski, R.; Penczek, S. Macromol. Rapid Commun. 1997, 18, 325.
55. (e) Dubois, P.; Jacobs, C.; Jérome, R.; Teysieé, P. Macromolecules 1991, 24, 2266.
56. Barakat, I.; Dubois, P.; Jérome, R.; Teyssie, P. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 505.
57. See, for example, refs 3a and 5c.
58. In principle, the Nd-bound ε-CL can be dissolved in a large amount of solvent, but at such high volumes, trace impurites lead to catalyst deactivation.
59. (a) Simic, V.; Pensec, S.; Spassky, N. Macromol. Symp. 2000, 153, 109.
60. (b) Duda, A.; Biela, T.; Libiszowski, J.; Penczek, S.; Dubois, P.; Mecerreyes, D.; Jérôme, R. Polym. Degrad. Stab. 1998, 59, 215.
61. (c) Song, C. X.; Feng, X. D. Macromolecules 1984, 17, 2764.
62. Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode: Methods in Enzymology; Academic Press: New York, 1997.
63. Altomare, A.; Cascarano, G.; Giacovazzo, G.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.
64. Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betteridge, P. W.; Cooper, R. I. CRYSTALS, issue 11; Chemical Crystallography Laboratory, University of Oxford, Oxford, U.K., 2001.