Cationic organomagnesium complexes as highly active initiators for the ring-opening polymerization of ε-caprolactone

Organometallics

Volumn 29, Issue 5, 2010, Pages 1079-1084

  Ireland, Benjamin J ^a   Wheaton, Craig A ^a   Hayes, Paul G ^a  

^a UNIVERSITY OF LETHBRIDGE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMBIENT TEMPERATURES; CAPROLACTONE; CATIONIC COMPLEXES; DIBENZOFURANS; HIGH ACTIVITY; HIGH MOLECULAR WEIGHT; ORGANOMAGNESIUM; PENTAFLUOROPHENYL; PHOSPHINIMINE;

CATIONIC POLYMERIZATION; DYES; POLYMERS;

RING OPENING POLYMERIZATION;

EID: 77749267600     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om900669y     Document Type: Article

References (43)

1. (a) Arshady, R. Biodegradable polymers: concepts, criteria, definitions. In Biodegradable Polymers; Arshady, R., Eds.;PBMSeries 2; Citus Books: London, UK, 2003; pp 1-34.
2. (b) Liebmann-Vinson, A.; Timmins, M. Biodegradable polymers: degradation mechanisms, part 2. In Biodegradable Polymers; Arshady, R., Eds.; PBM Series 2; Citus Books: London, UK, 2003; pp 329-372.
3. (a) Wheaton, C. A.; Hayes, P. G.; Ireland, B. J. Dalton Trans. 2009, 4832-4846.
4. (b) Platel, R. H.; Hodgson, L. M.;Williams, C. K. Polym. Rev. 2008, 48, 11-63.
5. (c) Wu, J.; Yu, T.-L.; Chen, C.-T., Lin, C.-C. Coord. Chem. Rev. 2006, 250, 602-626.
6. (d) Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. Chem. Rev. 2004, 104, 6147-6176.
7. (e) O'Keefe, B. J.; Hillmyer, M. A.; Tolman, W. B. J. Chem. Soc., Dalton Trans. 2001, 2215-2224.
8. Di Maio, E.; Innace, S.; Marrazzo, C.; Narkis, M.; Nicolais, L. Macromol. Symp. 2005, 228, 219-227.
9. Shimao, M. Curr. Opin. Biotechnol. 2001, 12, 242-247.
10. Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391-1434.
11. (a) Haddad, M.; Laghzaoui, M.; Welter, R.; Dagorne, S. Organometallics 2009, 28, 4584-4592.
12. (b) Dagorne, S.; Le Bideau, F.;Welter, R.; Bellemin-Laponnaz, S.; Maisse-François, A. Chem.; Eur. J. 2007, 13, 3202-3217.
13. (c) Milione, S.; Grisi, F.; Centore, R.; Tuzi, A. Organometallics 2006, 25, 266-274.
14. (d) Lewiński, J.; Horeglad, P.; Dranka, M.; Justyniak, I. Inorg. Chem. 2004, 43, 5789-5791.
15. (e) Hannant, M. D.; Schormann, M.; Bochmann, M. J. Chem. Soc., Dalton Trans. 2002, 4071-4073.
16. (f) Emig, N.; Nguyen, H.; Krautscheid, H.; Réau, R.; Cazaux, J. -B.; Bertrand, G. Organometallics 1998, 17, 3599-3608.
17. (a) Pajerski, A. D.; Squiller, E. P.; Parvez, M.; Whittle, R. R.; Richey, H. G. Organometallics 2005, 24, 809-814.
18. (b) Sarazin, Y.; Schormann, M.; Bochmann, M. Organometallics 2004, 23, 3296-3302.
19. Selected examples: (a) Schofield, A. D.; Barros, M. L.; Cushion, M. G.; Schwarz, A. D.; Mountford, P. Dalton Trans. 2009, 85-96.
20. (b) Wang, Z.-X.; Qi, C.-Y. Organometallics 2007, 26, 2243-2251.
21. (c) Sánchez-Barba, L. F.; Garcés, A.; Fajardo, M.; Alonso-Moreno, C.; Fernández-Baeza, J.; Otero, A.; Antiñolo, A.; Tejeda, J.; Lara-Śanchez, A.; López-Solera, M. I. Organometallics 2007, 26, 6403-6411.
22. (d) Sánchez-Barba, L. F.; Hughes, D. L.; Humphrey, S. M.; Bochmann, M.
23. (e)Yu, T.-L.;Wu, C.-C.; Chen, C.-C.; Huang, B.-H.; Wu, J.; Lin, C.-C. Polymer 2005, 46, 5909-5917.
24. (f) Shueh, M.-L.; Wang, Y.-S.; Huang, B.-H.; Kuo, C.-Y.; Lin, C.-C. Macromolecules 2004, 37, 5155-5162.
25. (g) Chisholm, M. H.; Eilerts, N. W.; Huffman, J. C.; Iyer, S. S.; Pacold, M.; Phomphrai, K. J. Am. Chem. Soc. 2000, 122, 11845-11854.
26. Odian, G. Principles of Polymerization, 4th ed.; John Wiley and Sons: New York, 2004; pp 19-586.
27. (a) Zhu, D.; Budzelaar, P. H. M. Organometallics 2008, 27, 2699-2705.
28. (b) Courtenay, S.; Walsh, D.; Hawkeswood, S.; Wei, P.; Das, A. K.; Stephan, D.W. Inorg. Chem. 2007, 46, 3623-3631.
29. (c) Welch, G. C.; Piers, W. E.; Parvez, M.; McDonald, R. Organometallics 2004, 23, 1811-1818.
30. (a) Ahmed, S. A.; Hill, M. S.; Hitchcock, P. B. Organometallics 2006, 25, 394-402.
31. (b) Wei, P.; Stephan, D. W. Organometallics 2003, 22, 601-604.
32. (a) Meyer, J.; Staudinger, H. Helv. Chim. Acta 1919, 2, 635-646.
33. (b) Alajarin, M.; Lopez-Leonardo, C. L.; Llamas-Lorente, P. L.; Bautista, D. Synthesis 2000, 14, 2085-2091.
34. Hannant, M. D.; Schormann, M.; Hughes, D. L.; Bochmann, M. Inorg. Chim. Acta 2005, 358, 1683-1691.
35. Wheaton, C. A.; Ireland, B. J.; Hayes, P. G. Organometallics 2009, 28, 1282-1285.
36. Krossing, I.; Raabe, I. Angew. Chem., Int. Ed. 2004, 43, 2066-2090.
37. (a) Horton, A. D.; de With, J.; van der Linden, A. J.; van de Weg, H. Organometallics 1996, 15, 2672-2674.
38. (b) Drewitt, M. J.; Niedermann, M.; Kumar, R.; Baird, M. C. Inorg. Chim. Acta 2002, 335, 43-51.
39. Roberts, J. A. S.; Chen, M.-C.; Seyam, A. M.; Li, L.; Zuccaccia, C.; Stahl, N. G.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 12713-12733.
40. Fontaine, F.-G. Personal communication. High molecular weight poly(ε-caprolactone) has proven impossible for the Fontaine group to observe by MALDI-ToF mass spectrometry.
41. Burger, B. J.; Bercaw J. E. Vacuum line techniques for handling air-sensitive organometallic compounds. In Experimental Organometallic Chemistry. A Practicum in Synthesis and Characterization; Wayda, A. L., Darensbourg, M. Y., Eds.; ACS Symposium Series 357; American Chemical Society: Washington DC, 1987; pp 79-98.
42. Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J. Organometallics 1995, 14, 3081-3089.
43. Murata, S.; Abe, S.; Tomioka, H. J. Org. Chem. 1997, 62, 3055-3061.