Carbonylative polymerization of oxetanes initiated by acetyl cobalt complexes

Chemistry - An Asian Journal

Volumn 3, Issue 4, 2008, Pages 710-718

  Permana, Yessi ^a   Nakano, Koji ^a   Yamashita, Makoto ^a   Watanabe, Daisuke ^a   Nozaki, Kyoko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Carbonylation; Cobalt; Lactones; Oxetanes; Ring opening polymerization

Indexed keywords

CARBON; COBALT; ETHER DERIVATIVE; OXETANE; POLYMER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CARBON; CATALYSIS; COBALT; ETHERS, CYCLIC; MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLYMERS;

EID: 47049094808     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700339     Document Type: Article

References (84)

1. For recent reviews, see: a) C. K. Williams, Chem. Soc. Rev. 2007, 36, 1573-1580;
2. b) M. Vert, Biomacromolecules 2005, 6, 538-546;
3. c) Y. Zheng, E. K. Yanful, A. S. Bassi, Crit. Rev. Biotechnol. 2005, 25, 243-250.
4. For recent reports on the biological processing of aliphatic polyesters, see: a) D. P. Martin, S. F. Williams, Biochem. Eng. J. 2003, 16, 97-105;
5. b) R. Carlson, F. Srienc, J. Biotechnol. 2006, 124, 561-573;
6. c) C. C. Chien, C. C. Chen, M. H. Choi, S. S. Kung, Y. H. Wei, J. Biotechnol. 2007, 132, 259-263;
7. d) L. L. Madison, G. W. Huisman, Microbiol. Mol. Biol. Rev. 1999, 63, 21-53.
8. For recent reviews, see: a) A. C. Albertsson, I. K. Varma, Adv. Polym. Sci. 2002, 157, 1-40;
9. b) O. Coulembiera, P. Degéea, J. L. Hedrick, P. Dubois, Prog. Polym. Sci. 2006, 31, 723-747.
10. For recent reports, see: a) M. Möller, R. Kånge, J. L. Hedrick, J. Polym. Sci. Part A 2000, 38, 2067-2074;
11. b) L. R. Rieth, D. R. Moore, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2002, 124, 15 239-15 248;
12. c) F. A. Jaipuri, B. D. Bower, N. L. Pohl, Tetrahedron: Asymmetry 2003, 14, 3249-3252;
13. d) K. M. Schreck, M. A. Hillmyer, Tetrahedron 2004, 60, 7177-7185;
14. e) B. C. Wilson, C. W. Jones, Macromolecules 2004, 37, 9709-9714;
15. f) F. Majoumo-Mbea, E. Smolensky, P. Lönnecke, D. Shpasser, M. S. Eisen, E. Hey-Hawkins, J. Mol. Catal. A 2005, 240, 91-98;
16. g) A. Amgoune, C. M. Thomas, S. Ilinca, T. Roisnel, J.-F. Carpentier, Angew. Chem. 2006, 118, 2848-2850;
17. Angew. Chem. Int. Ed. 2006, 45, 2782-2784;
18. h) B. G. G. Lohmeijer, R. C. Pratt, F. Leibfarth, J. W. Logan, D. A. Long, A. P. Dove, F. Nederberg, J. Choi, C. Wade, R. M. Waymouth, J. L. Hedrick, Macromolecules 2006, 39, 8574-8583;
19. i) W. Jeong, J. L. Hedrick, R. M. Waymouth, J. Am. Chem. Soc. 2007, 129, 8414-8415.
20. For recent reports on the ring-opening polymerization of lactides, see: a) B. J. O'Keefe, M. A. Hillmyer, W. B. Tolman, J. Chem. Soc. Dalton Trans. 2001, 2215-2224;
21. b) B. M. Chamberlain, M. Cheng, D. R. Moore, T. M. Ovitt, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2001, 123, 3229-3238;
22. c) T. M. Ovitt, G. W. Coates, J. Am. Chem. Soc. 2002, 124, 1316-1326;
23. d) Z. Zhong, P. J. Dijkstra, J. Feijen, Angew. Chem. 2002, 114, 4692-4695;
24. Angew. Chem. Int. Ed. 2002, 41, 4510-4513;
25. e) C. K. Williams, L. E. Breyfogle, S. K. Choi, W. Nam, V. G. Young, Jr., M. A. Hillmyer, W. B. Tolman, J. Am. Chem. Soc. 2003, 125, 11 350-11 359;
26. f) P. Hormnirun, E. L. Marshall, V. C. Gibson, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 2004, 126, 2688-2689;
27. g) D. Bourissou, B. Martin-Vaca, A. Dumitrescu, M. Graullier, F. Lacombe, Macromolecules 2005, 38, 9993-9998;
28. h) H. Y. Chen, H. Y. Tang, C. C. Lin, Macromolecules 2006, 39, 3745-3752;
29. i) L. M. Hodgson, A. J. P. White, C. K. Williams, J. Polym. Sci. Part A: Polym. Chem. 2006, 44, 6646-6651;
30. j) N. Nomura, R. Ishii, Y. Yamamoto, T. Kondo, Chem. Eur. J. 2007, 13, 4433-4451;
31. k) D. A. Culkin, W. Jeong, S. Csihony, E. D. Gomez, N. P. Balsara, J. L. Hedrick, R. M. Waymouth, Angew. Chem. 2007, 119, 2681-2684;
32. Angew. Chem. Int. Ed. 2007, 46, 2627-2630.
33. M. Hayakawa, M. Mitani, T. Yamada, T. Mukaiyama, Macromol. Chem. Phys. 1997, 198, 1305-1317.
34. R. Solaro, G. Cantoni, E. Chiellini, Eur. Polym. J. 1997, 33, 205-211.
35. M. Nishiura, Z. Hou, T. Koizumi, T. Imamoto, Y. Wakatsuki, Macromolecules 1999, 32, 8245-8251.
36. G. Odian, Principles of Polymerization, 4th ed., Wiley Interscience, New York, 2004, p. 581.
37. J. Kadokawa, Y. Iwasaki, H. Tagaya, Green Chem. 2002, 4, 14-16.
38. A. Duda, S. Penczek, Macromol. Chem. Phys. 1996, 197, 1273-1283.
39. S. Agarwal, X. Xie, Macromolecules 2003, 36, 3545-3549.
40. W. Saiyasombat, R. Molloy, T. M. Nicholson, A. F. Johnson, I. M. Ward, S. Poshyachinda, Polymer 1998, 39, 5581-5585.
41. a) A. Ohishi, Y. Taguchi, K. Fujita, Y. Ikeda, T. Masuda (Agency of Industrial Sciences and Technology, Japan), JP 3026216, B1 20000371, 2000;
42. b) A. Ohishi, Y. Taguchi, K. Fujita (National Institute of Advanced Industrial Science and Technology, Japan), JP 2003252968, A2 20030910, 2003.
43. J. Furukawa, Y. Iseda, T. Saegusa, H. Fujii, Makromol. Chem. 1965, 89, 263-268.
44. M. Allmendinger, R. Eberhardt, G. A. Luinstra, B. Rieger, J. Am. Chem. Soc. 2002, 124, 5646-5647.
45. D. Takeuchi, Y. Sakaguchi, K. Osakada, J. Polym. Sci. Part A: Polym. Chem. 2002, 40, 4530-4537.
46. M. Allmendinger, R. Eberhardt, G. A. Luinstra, B. Rieger, Macromol. Chem. Phys. 2003, 204, 564-569.
47. K. Nakano, K. Fumitaka, K. Nozaki, J. Polym. Sci. Part A: Polym. Chem. 2004, 42, 4666-4670.
48. J. T. Lee, H. Alper, Macromolecules 2004, 37, 2417-2421.
49. G. Liu, L. Jia, J. Am. Chem. Soc. 2004, 126, 14 716-14 717.
50. M. Allmendinger, F. Molnar, M. Zintl, G. A. Luinstra, P. P. Pflugl, B. Rieger, Chem. Eur. J. 2005, 11, 5327-5332.
51. Acetyl cobalt initiated copolymerization of aziridine with CO was also reported; see: a) L. Jia, E. Ding, W. R. Anderson, Chem. Commun. 2001, 1436-1437;
52. b) L. Jia, H. Sun, J. T. Shay, A. M. Allgeiger, S. D. Hanton, J. Am. Chem. Soc. 2002, 124, 7282-7283;
53. c) J. Zhao, E. Ding, A. M. Allgeiger, L. Jia, J. Polym. Sci. Part A: Polym. Chem. 2003, 41, 376-385;
54. d) D. J. Darensbourg, A. L. Phelps, N. L. Gall, L. Jia, J. Am. Chem. Soc. 2004, 126, 13 808-13 815;
55. e) H. Xu, N. L. Gall, L. Jia, W. W. Brennessel, B. E. Kucera, J. Organomet. Chem. 2005, 690, 5150-5158.
56. For a recent review on carbonylative polymerization of oxiranes, see: T. L. Church, Y. D. Y. L. Getzler, C. M. Byrne, G. W. Coates, Chem. Commun. 2007, 657-674.
57. Phosphine complex 1 was reported by Cowley and co-workers, but neither its structural analysis nor its catalytic application has been reported; see: S. A. Llewellyn, M. L. H. Green, A. R. Cowley, J. Organomet. Chem. 2005, 690, 2358-2364.
58. 3] was also synthesized and characterized; see: V. Galamb, G. Pályi, R. Boese, G. Schmid, Organometallics 1987, 6, 861-867.
59. C. A. Tolman, Chem. Rev. 1977, 77, 313.
60. J. S. Haasz, F. Haasz, V. Galamb, A. Benedetti, C. Zucchi, G. Pályi, J. Organomet. Chem. 1991, 419, 205-217.
61. C. H. Suresh, N. Koga, Inorg. Chem. 2002, 41, 1573-1578.
62. CCDC-663061 (1),-663062 (2), and-663063 (4) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre at www.ccdc.cam.ac.uk/data_request/cif.
63. [23e]
64. A. J. McAlees, R. McCrindle, A. R. Woon-Fat, Inorg. Chem. 1976, 15, 1065-1074.
65. See Supporting Information.
66. Examples of substitution reactions of sodium tetracarbonylcobaltate(-I): F. Ungvary, A. Wojcicki, J. Am. Chem. Soc. 1987, 109, 6848-6849.
67. Carbonylative ring expansion of oxetanes: a) M. D. Wang, S. Calet, H. Alper, J. Org. Chem. 1989, 54, 20-21;
68. b) Y. D. Y. L. Getzler, V. Kundnani, E. B. Lobkovsky, G.W. Coates, J. Am. Chem. Soc. 2004, 126, 6842-6843.
69. An example of ring-opening polymerization of oxetanes: S. Kanoh, A. Takeuchi, K. Fukuda, C. Chinwanitcharoen, M. Motoi, J. Polym. Sci. Part A: Polym. Chem. 2004, 42, 4570-4579.
70. For examples of carbonylative ring expansion of oxiranes, see: a) E. Drent, E. Kragtwijk (Shell Internationale Research Maatschappij, B. V., The Netherlands), Eur. Pat. Appl. EP 577206, 1994 [Chem. Abstr. 1994, 120, 191517 c];
71. b) J. T. Lee, P. J. Thomas, H. Alper, J. Org. Chem. 2001, 66, 5424-5426;
72. c) Y. D. Y. L. Getzler, V. Mahadevan, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2002, 124, 1174-1175;
73. d) V. Mahadevan, Y. D. Y. L. Getzler, G. W. Coates, Angew. Chem. 2002, 114, 2905-2908;
74. Angew. Chem. Int. Ed. 2002, 41, 2781-2784;
75. e) Y. D. Y. L. Getzler, V. Mahadevan, E. B. Lobkovsky, G. W. Coates, Pure Appl. Chem. 2004, 76, 557-564;
76. f) J. A. R. Schmidt, V. Mahadevan, Y. D. Y. L. Getzler, G. W. Coates, Org. Lett. 2004, 6, 373-376;
77. g) J. A. R. Schmidt, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2005, 127, 11 426-11 435;
78. h) J. W. Kramer, E. B. Lobkovsky, G. W. Coates, Org. Lett. 2006, 8, 3709-3712;
79. i) T. L. Church, Y. D. Y. L. Getzler, G. W. Coates, J. Am. Chem. Soc. 2006, 128, 10 125-10 133.
80. [20] to give 50% yield of the copolymer with an ester content of 42% (see Supporting Information); the employment of this catalyst system for the copolymerization of oxetane 5a and CO under similar reaction conditions gave a copolymer with a lower ester content (30%).
81. See Supporting Information.
82. W. F. Edgell, J. Lyford IV, Inorg. Chem. 1970, 9, 1932-1933.
83. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115-119.
84. G. M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures, University of Göttingen, Göttingen (Germany), 1997.