Polymer functionalization by free radical addition to alkynes

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 46, Issue 22, 2008, Pages 7386-7394

  Wu, Wei ^a   Parent, J Scott ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

Alkyne addition; Functionalization of polymers; Graft copolymers; Polyethers; reactive extrusion

Indexed keywords

ABS RESINS; ACETYLENE; ADDITION REACTIONS; CHEMICAL MODIFICATION; ETHERS; ETHYLENE; FREE RADICALS; FUNCTIONAL POLYMERS; GRAFT COPOLYMERS; GRAFTING (CHEMICAL); HYDROCARBONS; HYDROGEN; MODEL STRUCTURES; OLIGOMERIZATION; POLYETHERS; POLYETHYLENE OXIDES; POLYMERS; REACTION KINETICS;

ALKYNE ADDITION; ETHYL PROPIOLATE; FUNCTIONALIZATION OF POLYMERS; GOOD YIELDS; GRAFT STRUCTURES; HYDROGEN ATOMS; MODEL COMPOUNDS; POLY(ETHYLENE OXIDE); POLYMER FUNCTIONALIZATION; PRODUCT STRUCTURES; RADICAL ADDITIONS; REACTION YIELDS;

FREE RADICAL POLYMERIZATION;

EID: 56349149657     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.23043     Document Type: Article

References (47)

1. Russell, K. E. Prog Polym Sci 2002, 27, 1007-1038.
2. Moad, G. Prog Polym Sci 1999, 24, 81-142.
3. Parent, J. S.; Tripp, M.; Dupont J. Polym Eng Sci 2003, 43, 234-242.
4. Wong, W. K.; Varrall, D. C. Polymer 1994, 35, 5447-5452.
5. Vestberg, R.; Malkoch, M.; Kade, M.; Wu, P.; Fokin, V.V.; Sharpless, K. B.; Drockenmuller, E.; Hawker, C. J. J Polym Sci Part A: Polym Chem 2007, 45, 2835-2846.
6. Mitsui, H.; Hosoi, F.; Kagiya, T. Polym J 1974, 6, 20-26.
7. Amiel, Y. In The Chemistry of Functional Groups, Supplement, C; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1983; Chapter 10.
8. Julia, M. In The Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; pp 335-354.
9. Renaud, P.; Beaufils, F.; Feray, L.; Schenk, K. Angew Chem Int Ed 2003, 42, 4230-4233.
10. Curran, D. P.; Porter, N. A.; Geise, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995.
11. Cywinski, N. F.; Hepp, H. J. J Org Chem 1965, 30, 3814-3817.
12. Metzger, J. O.; Blumenstein, M. Chem Ber 1993, 126, 2493-2499.
13. Kopping, B.; Chatgilialoglu, C.; Zender, M.; Giese, B. J Org Chem 1992, 57, 3994-4000.
14. Giese, B.; Lachhein, S. Angew Chem Int Ed Engl 1982, 21, 768.
15. Fischer, H.; Radom, L. Angew Chem Int Ed Engl 2001, 40, 1340-1371.
16. Gaizith, M.; Szwarc, M. J Am Chem Soc 1957, 79, 3339-3343.
17. (a) Curran, D. P.; Dooseop, K.; Hong, T. L.; Shen, W. J Am Chem Soc 1988, 110, 5900-5902;
18. (b) Curran, D. P.; Shen, W. J Am Chem Soc 1993, 115, 6051-6059.
19. Drew, C. M.; Gordon, A. S. J Chem Phys 1959, 31, 1417-1481.
20. Giese, B.; Gonzalez-Gomez, J. A.; Lachhein, S.; Metzger, J. O. Angew Chem Int Ed 1987, 26, 479-480.
21. Rust, F. F. J Am Chem Soc 1957, 79, 4000-4003.
22. Russell, K. E.; Kelusky, E. C. J Polym Sci Part A: Polym Chem 1988, 26, 2273-2280.
23. Forsyth, J. C.; Baker, W. E.; Russell, K. E.; Whitney, R. A. J Polym Sci Part A: Polym Chem 1997, 35, 3517-3525.
24. (a) Kotha, S.; Brahmachary, E.; Lahiri, K. Eur J Org Chem 2005, 22, 4741-4767;
25. (b) Saito, S.; Yamamoto, Y. Chem Rev 2000, 100, 2901-2915.
26. Yamamoto, Y. Current Org Chem 2005, 9, 503-519.
27. (a) Zhu, Z.; Wang, J.; Zhang, Z.; Xiang, X.; Zhou, X. Organometallics 2007, 26, 2499-2500;
28. (b) Yang, J.; Verkade, J. G. Organometallics 2000, 19, 893-900;
29. (c) Yang, J.; Verkade, J. G. J Am Chem Soc 1998, 120, 6834-6835.
30. Cook, G. K.; Mayer, J. M. J Am Chem Soc 1995, 117, 7139-7156.
31. Bunce, N. J.; Hadley, M. J Org Chem 1974, 39, 2271-2276.
32. (a) Alfassi, Z. B.; Feldman, L. Int J Chem Kinet 1981, 13, 517-526;
33. (b) Parent, J. S.; Wu, W.; Sengupta, S. S.; Jackson, P. Eur Polym J 2006, 42, 971-980.
34. Fujisaki, N.; Ruf, A.; Gaumann T. J Am Chem Soc 1985, 107, 1605-1610.
35. Parent, J. S.; Parodi, R.; Wu, W. Polym Eng Sci 2006, 46, 1754-1761.
36. Sipos, A.; McCarthy, J.; Russell, K. J Polym Sci Part A: Polym Chem 1989, 27, 3353-3362.
37. Kharasch, M. S.; Jerome, J. J.; Urry, W. H. J Org Chem 1950, 15, 966-972.
38. Branchi, B.; Galli, C.; Gentili, P. Eur J Org Chem 2002, 16, 2844-2854.
39. McMillan, D. E.; Golden, P. M. Ann Rev Phys Chem 1982, 33, 493-532.
40. Bortel, E.; Lamot, R. Makromolekulare Chemie 1977, 178, 2617-2628.
41. Wang, J. H.; Schertz, D. M.; Golden, B. A. WO 99/ 33899, 1999.
42. (a) Row, P. D.; Thomas, D. K. J Appl Polym Sci 1963, 7, 461-468;
43. (b) Emami, S. H.; Salovey, R.; Hogen-Esch, T. E. J Polym Sci Part A: Polym Chem 2002, 40, 3021-3026.
44. Yakabe, Y.; Sudoh, Y.; Takahata, Y. J Chromatogr 1991, 558, 323-327.
45. Huggins, M. L. J Am Chem Soc 1942, 64, 2716-2718.
46. Nielsen, A. T.; Christian, S. L.; Moore, D. W.; Gilardi, R. D.; George, C. F. J Org Chem 1987, 52, 1656-1662.
47. Kumar, V. G.; Shoba, T. S.; Rao, K. V. C. Tetrahedron Lett 1985, 26, 6245-6248.