Organo-catalyzed ROP of ε-caprolactone: Methanesulfonic acid competes with trifluoromethanesulfonic acid

Macromolecules

Volumn 41, Issue 11, 2008, Pages 3782-3784

  Gazeau Bureau, Stéphanie ^a   Delcroix, Damien ^a   Martín Vaca, Blanca ^a   Bourissou, Didier ^a   Navarro, Christophe ^b   Magnet, Stéphanie ^b  

^a UMR 5069) 118 route de Narbonne   (France)

^b ARKEMA   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYST DEACTIVATION; CHEMICAL REACTIONS; LIVING POLYMERIZATION; MOLECULES; MONOMERS; ORGANIC COMPOUNDS; POLYMERIZATION; POLYMERS;

CAPROLACTONE (PCL); ENVIRONMENTALLY BENIGN; METHANE SULFONIC ACID (MSA); POLYDISPERSITIES (PDI); POLYMERIZATION TIME; RING-OPENING; SECONDARY ALCOHOLS; STOICHIOMETRIC RATIO (SR); TRIFLUOROMETHANESULFONIC ACID (TSFA);

CATALYST ACTIVITY;

EID: 45849130598     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma800626q     Document Type: Article

References (41)

1. (a) Löfgren, A.; Albertsson, A.-C.; Dubois, P.; Jérôme, R. Rev. Macromol. Chem. Phys. 1995, C35, 379-418.
2. (b) O'Keefe, B. J.; Hillmyer, M. A.; Tolman, W. B. J. Chem. Soc., Dalton Trans. 2001, 2215-2224.
3. (c) Lou, X.; Detrembleur, C.; Jérôme, R. Macromol. Rapid Commun. 2003, 24, 161-172.
4. (d) Albertsson, A.-C.; Varma, I. K. Biomacromolecules 2003, 4, 1466-1486.
5. (e) Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. Chem. Rev. 2004, 104, 6147-6176.
6. (f) Wu, J.; Yu, T.-L.; Chen, C.-T.; Lin, C.-C. Coord. Chem. Rev. 2006, 250, 602-626.
7. (a) Bourissou, D.; Moebs-Sanchez, S.; Martin-Vaca, B. C. R. Chim. 2007, 10, 115-194.
8. (b) Kamber, N. E.; Jeong, W.; Waymouth, R. M.; Pratt, R. C.; Lohmeijer, B. G. G.; Hedrick, J. L. Chem. Rev. 2007, 107, 5813-5840.
9. Nederberg, F.; Connor, E. F.; Moller, M.; Glauser, T.; Hedrick, J. L. Angew. Chem., Int. Ed. 2001, 40, 2712-2715.
10. (a) Dove, A. P.; Pratt, R. C.; Lohmeijer, B. G. G.; Culkin, D. A.; Hagberg, E. C.; Nyce, G. W.; Waymouth, R. M.; Hedrick, J. L. Polymer 2006, 47, 4018-4025.
11. (b) Dove, A. P.; Pratt, R. C.; Lohmeijer, B. G. G.; Li, H.; Hagberg, E. C.; Waymouth, R. M.; Hedrick, J. L. N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH: Weinheim, 2006; pp 275-296.
12. (a) Dove, A. P.; Pratt, R. C.; Lohmeijer, B. G. G.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2005, 127, 13798-13799.
13. (b) Pratt, R. C.; Lohmeijer, B. G. G.; Long, D. A.; Lundberg, P. N. P.; Dove, A. P.; Li, H. B.; Wade, C. G.; Waymouth, R.; Hedrick, J. L. Macromolecules 2006, 39, 7863-7871.
14. (a) Pratt, R. C.; Lohmeijer, B. G. G.; Long, D. A.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2006, 128, 4556-4557.
15. (b) Lohmeijer, B. G. G.; Pratt, R. C.; Leibfarth, F.; Logan, J. W.; Long, D. A.; Dove, A. P.; Nederberg, F.; Choi, J.; Wade, C.; Waymouth, R. M.; Hedrick, J. L. Macromolecules 2006, 39, 8574-8583.
16. (a) Zhang, L.; Nederberg, F.; Messman, J. M.; Pratt, R. C.; Hedrick, J. L.; Wade, C. G. J. Am. Chem. Soc. 2007, 129, 12610-12611.
17. (b) Zhang, L.; Nederberg, F.; Pratt, R. C.; Waymouth, R. M.; Hedrick, J. L.; Wade, C. G. Macromolecules 2007, 40, 4154-4158.
18. For theoretical and experimental mechanistic studies on organocatalyzed ROP, see: (a) Lai, C.; Lee, H. M.; Hu, C. Tetrahedron Lett. 2005, 46, 6265-6270.
19. (b) Csihony, S.; Nyce, G. W.; Sentman, A. C.; Waymouth, R. M.; Hedrick, J. L. Polym. Prep. (Am. Chem. Soc., Div. Polym. Chem.) 2004, 45, 319-320.
20. (c) Movassaghi, M.; Schmidt, M. A. Org. Lett. 2005, 7, 2453-2456.
21. (d) Simon, L.; Goodman, J. M. J. Org. Chem. 2007, 72, 9656-9662.
22. O-Carboxyanhydrides proved activated equivalents for 2,5-dioxane-1,4- diones toward DMAP-catalyzed ROP: (a) Thillaye du Boullay, O.; Marchai, E.; Martin-Vaca, B.; Cossio, F. P.; Bourissou, D. J. Am. Chem. Soc. 2006, 128, 16442-16443.
23. (b) Thillaye du Boullay, O.; Bonduelle, C.; Martin-Vaca, B.; Bourissou, D. Chem. Commun. 2008, 1786-1788.
24. (a) Kricheldorf, H. R.; Dunsing, R. Makromol. Chem. 1986, 187, 1611-1625.
25. (b) Kricheldorf, H. R.; Kreiser, I. Makromol. Chem. 1987, 188, 1861-1873.
26. (a) Shibasaki, Y.; Sanada, H.; Yokoi, M.; Sanda, F.; Endo, T. Macromolecules 2000, 33, 4316-4320.
27. (b) Sanda, F.; Sanada, H.; Shibasaki, Y.; Endo, T. Macromolecules 2002, 35, 680-683.
28. (c) Lou, X.; Detrembleur, C.; Jérôme, R. Macromolecules 2002, 35, 1190-1195.
29. For the preparation of di- and triblock copolymers from poly (ethylene glycol) macroinitiators, see: Kim, M. S.; Seo, K. S.; Khang, G.; Lee, H. B. Macromol. Rapid Commun. 2005, 26, 643-648.
30. Carboxylic acids have also been evaluated as catalysts for the ROP of e-caprolactone. See ref lib and Persson, P. V.; Schröder, J.; Wickholm, K.; Hedenström, E.; Iversen, T. Macromolecules 2004, 37, 5889-5893.
31. Bourissou, D.; Martin-Vaca, B.; Dumitrescu, A.; Graullier, M.; Lacombe, F. Macromolecules 2005, 38, 9993-9998.
32. (a) Basko, M.; Kubisa, P. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 7071-7081.
33. (b) Basko, M.; Kubisa, P. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 3090-3097.
34. For a recent discussion on the environmental benefits of MSA in the context of electrochemical processes, see: Gernon, M. D.; Wu, M.; Buszta, T.; Janney, P. Green Chem. 1999, 127-140.
35. Propylsulfonic acid immobilized on silica also proved effective for the controlled ROP of e-caprolactone: Wilson, B. C.; Jones, C. W. Macromolecules 2004, 37, 9709-9714.
36. (a) Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463.
37. (b) Pataï, S.; Rappoport, Z. In The Chemistry of Sulphonic Acids, Esters and their Derivatives; John Wiley and Sons: New York, 1991; p 251.
38. Baker, S. C.; Kelly, D. P.; Murrell, J. C. Nature (London) 1991, 350, 627-628.
39. Save, M.; Schappacher, M.; Soum, A. Macromol. Chem. Phys. 2002, 203, 889-899.
40. See Supporting Information for details.
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