Synthesis of hyperbranched poly(aryl ether)s via carbene insertion processes

Macromolecules

Volumn 40, Issue 4, 2007, Pages 939-949

  Blencowe, Anton ^a   Caiulo, Nick ^a   Cosstick, Kevin ^b   Fagour, William ^a   Heath, Peter ^a   Hayes, Wayne ^a  

^a UNIVERSITY OF READING   (United Kingdom)

^b Invista   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; GEL PERMEATION CHROMATOGRAPHY; HOMOPOLYMERIZATION; MOLECULAR WEIGHT; MONOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; SYNTHESIS (CHEMICAL);

CARBENE INSERTION PROCESSES; DIAZIRINE MONOMERS; POLY(ARYL ETHER)S;

POLYETHERS;

EID: 33847699395     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma061951l     Document Type: Article

References (53)

1. Doyle, M. P. React. Intermed. Chem. 2004, 561.
2. Blencowe, A.; Hayes, W. Soft Matter 2005, 1, 178.
3. (a) Moloney, M. G.; Ebenezer, W.; Awenat, K. M. Patent: US 6699527, 2000.
4. (b) Awenat, K. M.; Davis, P. J.; Moloney, M. O.; Ebenezer, W. Chem. Commun. 2005, 990.
5. Blencowe, A.; Cosstick, K.; Hayes, W. New J. Chem. 2006, 1, 53.
6. Meerwein, H. Angew. Chem. 1948, 60, 78.
7. Gutsche, C. D.; Kinoshita, K. J. Org. Chem. 1963, 28, 1762.
8. Kubota, H.; Morawetz, H. J. Polym. Sci., Polym. Chem. Ed. 1967, 5, 585.
9. Kantor, S. W.; Osthoff, R. C. J. Am. Chem. Soc. 1953, 75, 931.
10. Imoto, M.; Nakaya, T. J. Macromol. Sci., Rev. Macromol. Chem. 1972, C7, 1.
11. Mucha, M.; Wunderlich, B. J. Polym. Sci., Polym. Phys. 1974, 12, 1993.
12. Bawn, C. E. H.; Rhodes, T. B. Trans. Faraday Soc. 1954, 50, 934.
13. Van Gaver, G. S.; Magni, R. Patent: FR 1313247, 1962.
14. Leffler, J. E.; Ramsey, B. G. Proc. Chem. Soc. 1961, 117.
15. (a) Dorion, G. H.; Polchlopek, S. E.; Sheers, E. H. Angew. Chem. 1964, 76, 495.
16. (b) Dorion, G. H.; Sheers, E. H. Patent: US 3255124, 1966.
17. Bawn, C. E. H.; Ledwith, A.; Matthies, P. J. Polym. Sci. 1958, 33, 21.
18. Richardson, M. J.; Flory, P. J.; Jackson, J. B. Polymer 1963, 4, 221.
19. Buckley, G. D.; Ray, N. H. J. Chem. Soc. 1952, 3701.
20. Krakovyak, M. G.; Anufrieva, E. V.; Skorokhodov, S. S. Patent: SU 319610, 1971.
21. Bai, J.; Shea, K. J. Polym. Prepr. 2005, 46, 765.
22. Shea, K. J.; Walker, J. W.; Zhu, H.; Paz, M.; Greaves, J. J. Am. Chem. Soc. 1997, 119, 9049.
23. Goubeau, P.; Rohwedder, H. Annalen 1957, 604, 168.
24. Davies, A. G.; Hare, D. G.; Khan, O. R.; Sikora, J. J. Chem. Soc. 1963, 4461.
25. Bawn, C. E. H.; Ledwith, A.; Matthies, P. J. Polym. Sci. 1958, 34, 93.
26. Werner, H.; Richards, J. H. J. Am. Chem. Soc. 1968, 90, 4976.
27. Feltzin, J.; Restaino, A. J.; Mesrobian, R. B. J. Am. Chem. Soc. 1955, 77, 206.
28. (a) Nasini, A. G.; Trossarelli, L.; Saini, G. Makromol. Chem. 1961, 550, 44-46.
29. (b) Nasini, A. G.; Saini, G.; Trossarelli, L. Pure Appl. Chem. 1962, 4, 255.
30. McCrindle, R.; Arsenault, G. J.; Farwaha, R.; Hampden-Smith, M. J.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1986, 943.
31. Fischer, F.; Tropsch, H. Brennst.-Chem. 1926, 7, 96.
32. Brady, R. C.; Pettit, R. J. Am. Chem. Soc. 1980, 102, 6182.
33. (a) Hermans, J. C.; Smets, G. J. Patent: GB 1142165, 1969.
34. (b) Smets, G. J.; Bracke, W.; Hermans, J. C. Pure Appl. Chem. 1969, 15, 525.
35. Richards, F. M.; Lamed, R.; Wynn, R.; Patel, D.; Olack, G. Protein Sci. 2000, 9, 2506.
36. Bruce, J. M.; Creed, D.; Dawes, K. J. Chem. Soc. (C) 1971, 2244.
37. Beumer, R.; Bayon, P.; Bugada, P.; Ducki, S.; Mongelli, N.; Sirtori, F. R.; Telser, J.; Gennari, C. Tetrahedron 2003, 59, 8803.
38. (a) Brunner, J.; Senn, H.; Richards, F. M. J. Biol. Chem. 1980, 255, 3313.
39. (b) Bennett, P.; Harwood, L. M.; Macro, J.; McGregor, A. J. Chem. Soc., Chem. Commun. 1994, 961.
40. (a) Jennings, B. M.; Liu, M. T. H. J. Am. Chem. Soc. 1976, 98, 6416.
41. (b) Liu, M. T. H.; Ramakrishnan, K. J. Org. Chem. 1977, 42, 3450.
42. (a) Doyle, M. P.; Devia, A. H.; Bassett, K. E.; Terpstra, J. W.; Mahapatro, S. N. J. Org. Chem. 1987, 52, 1619.
43. (b) Bonneau, R.; Liu, M. T. H. J. Phys. Chem. A 2000, 104, 4115.
44. Reactive Intermediate Chemistry; Moss, R., Platz, M. S., Jones, M., Eds.; Wiley: Hoboken, NJ, 2004.
45. (a) Richard, J. P. J. Am. Chem. Soc. 1989, 111, 1455.
46. (b) Richard, J. P. J. Am. Chem. Soc. 1989, 111, 6735.
47. (c) Richard, J. P.; Amges, T. L.; Vontor, T. J. Am. Chem. Soc. 1992, 114, 5626.
48. Tusji, Y.; Toteva, M. M.; Garth, H. A.; Richard, J. P. J. Am. Chem. Soc. 2003, 125, 15455.
49. Brahms, D. L. S.; Dailey, W. P. Chem. Rev. 1996, 96, 1585.
50. 19F NMR shift values and coupling constants for trifluoromethyl groups is provided in the Supporting Information.
51. (a) Hawker, C. J.; Fréchet, J. M. J.; Grubbs, R. B.; Dao, J. J. Am. Chem. Soc. 1995, 117, 10763.
52. (b) Fréchet, J. M. J.; Henmi, M.; Gitsov, I.; Aoshima, S.; Leduc, M. R.; Grubbs, R. B. Science 1995, 269, 1080.
53. Crystallographic data for compound 3 are provided in the Supporting Information.