Living polymerization of sulfur ylides. Synthesis of terminally functionalized and telechelic polymethylene

Macromolecules

Volumn 35, Issue 22, 2002, Pages 8330-8337

  Busch, Brett B ^a   Staiger, Chad L ^a   Stoddard, Jonathan M ^a   Shea, Kenneth J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROBORATION;

CATALYSIS; LIVING POLYMERIZATION; MOLECULAR WEIGHT; OLEFINS; OXIDATION; SUBSTITUTION REACTIONS;

FUNCTIONAL POLYMERS;

EID: 0037159317     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma020729n     Document Type: Article

References (70)

1. Zhang, Z.; Ying, S.; Hu, Q.; Xu, X. J. Appl. Polym. Sci. 2002, 83, 2625.
2. Sriram, V.; Subramani, S.; Radhakrishnan, G. Polym. Int. 2001, 50, 1124.
3. Du, J.; Peng, Y.; Zhang, T.; Ding, X.; Zheng, Z. J. Appl. Polym. Sci. 2002, 83, 1678.
4. Sekkar, V.; Venkatachalam, S.; Ninan, K. Eur. Polym. J. 2002, 38, 169.
5. Tsukahara, Y.; Ismail, H.; Takenaka, K.; Yoshimoto, N.; Kaeriyama, K. Polym. Int. 1999, 48, 398.
6. Vlassopoulos, D.; Pitsikalis, M.; Hadjichristidis, N. Macromolecules 2000, 33, 9740.
7. Martuscelli, E.; Musto, P.; Ragosta, G.; Riva, F.; Mascia, L. J. Mater. Sci. 2000, 35, 3719.
8. Wagener, K.; Batich, C.; Kirsch, B.; Wanigatunga, S. J. Polym. Sci., Part A: Polym. Chem. 1989, 27, 2625.
9. Tonelli, C.; Gavezotti, P.; Strepparola, E. J. Fluorine Chem. 1999, 95, 51.
10. Dubois, P.; Jerome, R.; Teyssie, P. Mater. Sci. Technol. 1999, 20, 195.
11. Hong, K.; Uhrig, D.; Mays, J.W. Curr. Opin. Solid State Mater. Sci. 1999, 4, 531.
12. Bisht, H.S.; Chatterjee, A.K. J. Macromol. Sci., Polym. Rev. 2001, C41, 139.
13. Matyjaszewski, K. Chem. Rev. 2001, 101, 2921.
14. Korolev, G.V.; Marchenko, A.P. Russ. Chem. Rev. 2000, 69, 409.
15. Stridsberg, K.M.; Ryner, M.; Albertsson, A.-C. Adv. Polym. Sci. 2002, 157, 41.
16. Agarwal, S.; Mast, C.; Dehnicke, K.; Greiner, A. Macromol. Rapid Commun. 2000, 21, 1952.
17. Xudong, L.; Detrembleur, C.; Robert, J. Macromolecules 2002, 35, 1190.
18. Hashimoto, K. Prog. Polym. Sci. 2000, 25, 1411.
19. Grubbs, R.H.; Khosravi, E. Mater. Sci. Technol. 1999, 20, 65.
20. Buchmeiser, M.R. Chem. Rev. 2000, 100, 1565.
21. Piotti, M.E. Curr. Opin. Solid State Mater. Sci. 1999, 4, 539.
22. Podesva, J.; Holler, P. J. Appl. Polym. Sci. 1999, 74, 3203.
23. Jang, Y.-C.; Kim, P.-J.; Kwag, G.-H.; Kim, A.; Lee, S.-H. US Pat. Appl. Publ., US 20020016423, 2002.
24. Pradel, J.L.; Boutevin, B.; Ameduri, B. J. Polym. Sci., Part A: Polym. Chem. 2000, 34, 7034.
25. Fernyhough, C.M.; Young, R.N. Macromolecules 2001, 34, 7034.
26. Grubbs, R.H.; Morita, T.; Maughon, B.R.; Bielawski, C.W. Macromolecules 2000, 33, 6621.
27. Brookhart, M.; Desimone, J.M.; Grant, B.E.; Tanner, M.J. Macromolecules 1995, 28, 5378.
28. Shea, K.J.; Zhu, H.; Walker, J.R.; Paz, M.M.; Greaves, J. J. Am. Chem. Soc. 1997, 119, 9049.
29. Shea, K.J.; Busch, B.B.; Paz, M.M. Angew. Chem., Int. Ed. Engl. 1998, 38, 1391.
30. Shea, K.J.; Lee, S.Y.; Busch, B.B. J. Org. Chem. 1998, 63, 5746.
31. Shea, K.J. Chem. Eur.J. 2000, 6, 1113.
32. Shea, K.J.; Wagner, C.E. Org. Lett. 2001, 3, 3063.
33. Shea, K.J.; Busch, B.B.; Paz, M.M.; Staiger, C.L.; Stoddard, J.M.; Walker, J.R.; Zhou, X.; Zhu, H. J. Am. Chem. Soc. 2002, 124, 3636.
34. Shea, K.J.; Zhou, X.-Z. J. Am. Chem. Soc. 2000, 122, 11515.
35. Brown, H.C. Organic Synthesis via Boranes; Wiley-Interscience: New York, 1975.
36. Pelter, A.; Smith, K.; Brown, H.C. Borane Reagents; Academic Press: New York, 1988.
37. Thomas, S.E. Organic Synthesis: The Role of Boron and Silicon; Oxford University Press: New York, 1994.
38. Matteson, D.S. Stereodirected Synthesis with Organoboranes; Springer-Verlag: Berlin, 1995.
39. Bergbreiter, D.; Gray, H.N.; Srinivas, B. Macromolecules 1994, 27, 7294.
40. Jerabek, K.; Shea, K.J.; Sasaki, D.Y.; Stoddard, G.J. J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 605.
41. Ivanov, V.B.; Behnisch, J.; Hollaender, A.; Mehdorn, F.; Zimmermann, H. Surf. Interface Anal. 1996, 24, 257.
42. Aplin, J.D.; Hughes, R.C. Anal. Biochem. 1981, 113, 144.
43. Singhvi, R.; Kumar, A.; Lopez, G.P.; Stephanopoulos, G.N.; Wang, D.I.; Whitesides, G.M.; Ingber, D.E. Science 1994, 264, 696.
44. Sundberg, S.A.; Barrett, R.W.; Pirrung, M.; Lu, A.L.; Kiangsoontra, B.; Holmes, C.P. J. Am. Chem. Soc. 1995, 117, 12050.
45. Mrksich, M.; Whitesides, G.M. Annu. Rev. Biophys. Biomol. Struct. 1996, 25, 55.
46. Gough, A.H.; Jung, D.R.; Taylor, D.L. PCT Int. Appl., WO 0017624, 1999.
47. Bruening, R.L.; Krakowiak, K.E. PCT Int. Appl., WO 0076616, 2000.
48. Novaimi, M.; Moschel, K.; Bisswanger, H. Enzyme Microbial Technol. 2001, 29, 567.
49. Xue, H.; Bhowmik, P.; Schlick, S. Macromolecules 1993, 26, 3340.
50. Xue, H.; Xu, S.; Bhowmik, P.; Schlick, S. Macromolecules 1995, 28, 3351.
51. Xu, J.; Dimonie, V.; Sudol, E.; Klein, A.; El-Aasser, M. J. Appl. Polym. Sci. 1998, 69, 985.
52. Xu, J.; Dimonie, V.; Sudol, E.; Shaffer, O.; El-Aasser, M. J. Appl. Polym. Sci. 1998, 69, 977.
53. Xu, J.; Dimonie, V.; Sudol, E.; El-Aasser, M. J. Appl. Polym. Sci. 1998, 69, 965.
54. Takasu, M.; Yamamoto, H. Synlett 1990, 4, 1946.
55. Bertozzi, C.R.; Bednarski, M.D. J. Org. Chem. 1991, 56, 4326.
56. Ruyter, C.M.; Stockigt, J.H. Helv. Chim. Acta 1991, 74, 1703.
57. Cruz, A.; Geniz, E.; Contreras, R. Tetrahedron: Asymmetry 1998, 9, 3991.
58. Hosomi, A.; Sakata, Y.; Sakarai, H. Tet. Lett. 1984, 25, 2383.
59. Potter, B.V.; Marwood, R.D.; Riley, A.M.; Jenkins, D.J. J. Chem. Soc., Perkin Trans. 1 2000, 12, 1935.
60. Kabalka, G.W.; Li, N.S.; Pace, R.D. Synth. Commun. 1995, 25, 2135.
61. Overman, L.; Okazaki, M.; Mishra, P. Tetrahedron Lett. 1986, 47, 4391.
62. Benmaarouf-Khallaayoun, Z.; Baboulene, M.; Speziale, V.; Lattes Phosphorus Sulfur 1998, 36, 181.
63. Brown, H.C. Hydroboration; Benjamin: New York, 1962.
64. Onak, T. Organoborane Chemistry; Academic Press: New York, 1975.
65. Brown, H.C.; Chandrasekharan, J. J. Org. Chem. 1988, 53, 4811.
66. Belu, A.M.; Desimone, J.M.; Linton, R.W.; Lange, G.W.; Friedman, R.M. J. Am. Soc. Mass Spectrom. 1996, 7, 11.
67. Bauer, B.J.; Wallace, W.E.; Fanconi, B.M.; Guttman, C.M. J. Am. Soc. Mass Spectrom. 2001, 1186.
68. Chen, R.; Li, L. J. Am. Soc. Mass Spectrom. 2001, 12, 367.
69. Kahr, M.S.; Wilkins, C.L. J. Am. Soc. Mass Spectrom. 1993, 12, 367.
70. We have not yet analyzed trimethylsilyl, tri-n-butyltin, biotin, mannose, pegalated dansyl, and pegalated pyrene by MALDI-TOF.