Ring-opening polymerization of lactones using binaphthyl-diyl hydrogen phosphate as organocatalyst and resulting monosaccharide functionalization of polylactones

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 51, Issue 10, 2013, Pages 2279-2287

  Miao, Yong ^a,b,c   Phuphuak, Yupin ^d   Rousseau, Cyril ^a,e   Bousquet, Till ^a,b,c   Mortreux, André ^a,b,c   Chirachanchai, Suwabun ^d   Zinck, Philippe ^a,b,c  

^a UNIV LILLE   (France)

^b Ecole Nationale Superieure de Chimie de Lille   (France)

^c UNITÉ DE CATALYSE ET DE CHIMIE DU SOLIDE   (France)

^d CHULALONGKORN UNIVERSITY   (Thailand)

^e UNIVERSITÉ D'ARTOIS   (France)

Author keywords

biopolymers; catalysis; cationic polymerization; polyesters; ring opening polymerization

Indexed keywords

BENZYL ALCOHOL; END-FUNCTIONALIZATION; FUNCTIONALIZATIONS; HYDROGEN PHOSPHATES; HYDROXYL GROUPS; INITIATION EFFICIENCY; ORGANOCATALYSTS; SHORT REACTION TIME;

BIOPOLYMERS; CARBOHYDRATES; CATALYSIS; CATIONIC POLYMERIZATION; HYDROGEN; POLYESTERS;

CATALYSTS;

EID: 84876007674     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.26612     Document Type: Article

References (43)

1. M. K. Kiesewetter, E. I. Shin, J. L. Hedrick, R. M. Waymouth, Macromolecules 2010, 43, 2093-2107.
2. Y. Shibasaki, H. Sanada, M. Yokoi, F. Sanda, T. Endo, Macromolecules 2000, 33, 4316-4320.
3. X. Lou, C. Detrembleur, R. Jérôme, Macromolecules 2002, 35, 1190-1195.
4. F. Sanda, H. Sanada, Y. Shibasaki, T. Endo, Macromolecules 2002, 35, 680-683.
5. J. Casas, P. V. Persson, T. Iversen, A. Cõrdova, Adv. Synth. Catal. 2004, 346, 1087-1089.
6. P. V. Persson, J. Schroder, K. Wickholm, E. Hendenstrom, T. Iversen, Macromolecules 2004, 37, 5889-5893.
7. D. Bourissou, B. Martin-Vaca, A. Dumitrescu, M. Graullier, F. Lacombe, Macromolecules 2005, 38, 9993-9998.
8. S. Gazeau-Bureau, D. Delcroix, B. Martin-Vaca, D. Bourissou, C. Navarro, S. Magnet, Macromolecules 2008, 41, 3782-3784.
9. M. Basko, P. Kubisa, J. Polym. Sci. Part A: Polym. Chem. 2006, 44, 7071-7081.
10. M. Basko, P. Kubisa, J. Polym. Sci. Part A: Polym. Chem. 2007, 45, 3090-3097.
11. M. Basko, P. Kubisa, J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 7919-7923.
12. M. Basko, P. Kubisa, J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 2650-2658.
13. F. A. Jaipuri, B. D. Bower, N. L. Pohl, Tetrahedron: Asymmetry 2003, 14, 3249-3252.
14. N. Susperregui, D. Delcroix, B. Martin-Vaca, D. Bourissou, L. Maron, J. Org. Chem. 2010, 75, 6581-6587.
15. F. Nederberg, E. F. Connor, M. Möller, T. Glauser, J. L. Hedrick, Angew. Chem. 2001, 40, 2712-2715.
16. B. G. G. Lohmeijer, R. C. Pratt, F. Leibfarth, J. W. Logan, D. A. Long, P. A. Dove, F. Nederberg, J. Choi, C. Wade, R. M. Waymouth, J. L. Hedrick, Macromolecules 2006, 39, 8574-8583.
17. C. Thomas, F. Peruch, A. Deffieux, A. Milet, J. P. Desvergne, B. Bibal, Adv. Synth. Catal. 2011, 353, 1049-1054.
18. M. Myers, E. F. Connor, T. Glauser, A. Möck, G. Nyce, J. L. Hedrick, J. Polym. Sci. Part A: Polym. Chem. 2002, 40, 844-851.
19. E. F. Connor, G. Nyce, M. Myers, A. Möck, J. L. Hedrick, J. Am. Chem. Soc. 2002, 124, 914-915.
20. C. Navarro, D. Bourissou, B. Martin-Vaca, D. Delcroix,. Fr. Patent PCT/0958742, 12, 2009.
21. K. Makiguchi, T. Satoh, T. Kakuchi, Macromolecules 2011, 44, 1999-2005.
22. D. Delcroix, A. Couffin, N. Susperregui, C. Navarro, L. Maron, B. Martin-Vaca, D. Bourissou, Polym. Chem. 2011, 2, 2249-2256.
23. A. Cõrdova, T. Iversen, K. Hult, Macromolecules 1998, 31, 1040-1045.
24. K. S. Bisht, F. Deng, R. A. Gross, D. L. Kaplan, G. Swift, J. Am. Chem. Soc. 1998, 120, 1363-1367.
25. F. Deng, K. S. Bisht, A. R. Gross, D. L. Kaplan, Macromolecules 1999, 12, 5159-5161.
26. K. Yasugi, T. Nakamura, Y. Nagasaki, M. Kato, K. Kataoka, Macromolecules 1999, 32, 8024-8032.
27. T. Ouchi, T. Uchida, Y. Ohya, Macromol. Biosci 2001, 1, 371-375.
28. T. Hamaide, M. Pantiru, H. Fessi, P. Boullanger, Macromol. Rapid Commun. 2001, 22, 659-663.
29. K. Bernard, P. Degée, P. Dubois, Polym. Int. 2003, 52, 406-411.
30. M. Pantiru, C. Iojoiu, T. Hamaide, F. Delolme, Polym. Int. 2004, 53, 506-514.
31. C. K. Williams, Chem. Soc. Rev. 2007, 36, 1573-1580.
32. Y. Morikawa, H. Kinoshita, M. Asahi, A. Takasu, T. Hirabayashi, Polym. J. 2008, 40, 217-222.
33. M. Tang, F. A. Haider, C. Minelli, M. M. Stevens, C. K. Williams, J. Polym. Sci. A 2008, 46, 4352-4362.
34. S. Vuorinen, J. Heinämäki, O. Antikainen, M. Lahcini, T. Repo, J. Yliruusi, AAPS Pharm. Sci. Tech. 2009, 10, 566-573.
35. P. Zinck, Rev. Environ. Sci. Biotech. 2009, 8, 231-234.
36. Y. Miao, C. Rousseau, A. Mortreux, P. Martin, P. Zinck, Polymer 2011, 52, 5018-5026.
37. P. Zinck, In Biomedical Engineering, Trends in Materials Science;, A. N. Laskovski, Ed.; Intech: Vienna, 2011; pp. 489-512 (http://www.intechopen.com/ articles/show/title/synthetic-strategies-for-biomedical-polyesters-specialties).
38. Q. Hao, F. Li, Q. Li, Y. Li, L. Jia, J. Yang, Q. Fang, A. Cao, Biomacromolecules 2005, 6, 2236-2247.
39. Y. Miao, P. Zinck, Polym. Chem. 2012, 3, 1119-1122.
40. J. Jacques, C. Fouquey, Org. Synth. 1993, 8, 50.
41. M. Save, M. Schappacher, A. Soum, Macromol. Chem. Phys. 2002, 203, 889-899.
42. Y. Okamoto, Makromol. Chem. Makromol. Symp. 1991, 42-43, 117-133.
43. P. Kubisa, S. Penczek, Prog. Polym. Sci. 1999, 24, 1409-1437.