Hypervalent iodine-mediated direct azidation of polystyrene and consecutive click-type functionalization

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 48, Issue 4, 2010, Pages 966-974

  Tsarevsky, Nicolay V ^a  

^a ATRP Solutions Inc   (United States)

Author keywords

Functionalization of polymers; Graft copolymers; Polystyrene

Indexed keywords

AZIDATION; AZIDE GROUP; ELEMENTAL ANALYSIS; FUNCTIONALIZATION OF POLYMERS; FUNCTIONALIZATIONS; HYPERVALENT IODINE; HYPERVALENT IODINE COMPOUNDS; MONOMETHYL ETHERS; PENDANT GROUPS; POLYMER BACKBONES; POLYMERIC BRUSHES; SEMI-QUANTITATIVE; SIDE CHAINS; TRIMETHYLSILYL AZIDE;

BENZENE; COPOLYMERIZATION; ETHANE; ETHERS; ETHYLENE; GRAFT COPOLYMERS; GRAFTING (CHEMICAL); INDUSTRIAL CHEMICALS; IODINE; IODINE COMPOUNDS; POLYETHYLENE OXIDES; POLYSTYRENES; STYRENE; SYNTHESIS (CHEMICAL);

FUNCTIONAL POLYMERS;

EID: 77958557582     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.23854     Document Type: Article

References (71)

1. Boyer, J. H.; Canter, F. C. Chem Rev 1954, 54, 1-57.
2. L'Abbe, G. Chem Rev 1969, 69, 345-363.
3. Sheradsky, T. In The Chemistry of the Azido Group; Patai, S., Ed.; Interscience: London, 1971; pp 331-395.
4. Scriven, E. F. V.; Turnbull, K. Chem Rev 1988, 88, 297-368.
5. Huisgen, R. 1,3-Dipolar Cycloaddition Chemistry; Wiley: New York, 1984; Vol. 1.
6. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew Chem Int Ed 2002, 41, 2596-2599.
7. Tornoe, C. W.; Christensen, C.; Meldal, M. J Org Chem 2002, 67, 3057-3064.
8. Meldal, M.; Tornoe, C. W. Chem Rev 2008, 108, 2952-3015.
9. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew Chem Int Ed 2001, 40, 2004-2021.
10. Sumerlin, B. S.; Tsarevsky, N. V.; Gao, H.; Golas, P.; Louche, G.; Lee, R. Y.; Matyjaszewski, K. ACS Symp Ser 2006, 944, 140-152.
11. Binder, W. H.; Sachsenhofer, R. Macromol Rapid Commun 2007, 28, 15-54.
12. Golas, P. L.; Matyjaszewski, K. QSAR Comb Sci 2007, 26, 1116-1134.
13. Lutz, J.-F. Angew Chem Int Ed 2007, 46, 1018-1025.
14. Fournier, D.; Hoogenboom, R.; Schubert, U. S. Chem Soc Rev 2007, 36, 1369-1380.
15. Lutz, J.-F.; Schlaad, H. Polymer 2008, 49, 817-824.
16. Iha, R. K.; Wooley, K. L.; Nystrom, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Chem Rev 2009, 109, 5620-5686.
17. Helms, B.; Mynar, J. L.; Hawker, C. J.; Frechet, J. M. J. J Am Chem Soc 2004, 126, 15020-15021.
18. Malkoch, M.; Thibault, R. J.; Drockenmuller, E.; Messersch-midt, M.; Voit, B.; Russell, T. P.; Hawker, C. J. J Am Chem Soc 2005, 127, 14942-14949.
19. Cheradame, H.; De la Croix Habimana, J.; Rousset, E.; Chen, F. Makromol Chem 1991, 192, 2777-2789.
20. Sumerlin, B. S.; Tsarevsky, N. V.; Louche, G.; Lee, R. Y.; Matyjaszewski, K. Macromolecules 2005, 38, 7540-7545.
21. Li, Y.; Yang, J.; Benicewicz, B. C. J Polym Sci Part A: Polym Chem 2007, 45, 4300-4308.
22. Takeishi, M.; Okawara, M. J Polym Sci Polym Lett Ed 1969, 7, 201-203.
23. Iizawa, T.; Nishikubo, T.; Masuda, Y.; Okawara, M. Macro-molecules 1984, 17, 992-998.
24. Roush, W. R.; Feitler, D.; Rebek, J. Tetrahedron Lett 1974, 15, 1391-1392.
25. Schuh, K.; Prucker, O.; Ruehe, J. Macromolecules 2008, 41, 9284-9289.
26. Nishikubo, T.; Iizawa, T.; Numazaki, N.; Okawara, M. Makro-mol Chem Rapid Commun 1983, 4, 187-191.
27. O'Reilly, R. K.; Joralemon, M. J.; Wooley, K. L.; Hawker, C. J Chem Mater 2005, 17, 5976-5988.
28. Tsarevsky, N. V.; Bencherif, S. A.; Matyaszewski, K. Macro-molecules 2007, 40, 4439-4445.
29. Musher, J. M. Angew Chem Int Ed 1969, 8, 54-68.
30. Martin, J. C. Science 1983, 221, 509-514.
31. Sandin, R. B. Chem Rev 1943, 32, 249-276.
32. Banks, D. F. Chem Rev 1966, 66, 243-266.
33. Varvoglis, A. Synthesis 1984, 709-726.
34. Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992.
35. Stang, P. J.; Zhdankin, V. V. Chem Rev 1996, 96, 1123-1178.
36. Varvoglis, A. Tetrahedron 1997, 53, 1179-1255.
37. Zhdankin, V. V.; Stang, P. J. Chem Rev 2002, 102, 2523-2584.
38. Zhdankin, V. V.; Stang, P. J. Chem Rev 2008, 108, 5299-5358.
39. Varvoglis, A. Chem Soc Rev 1981, 10, 377-407.
40. Muraki, T.; Togo, H.; Yokoyama, M. Rev Heteroat Chem 1997, 17, 213-243.
41. Magnus, P.; Lacour, J.; Weber, W. J Am Chem Soc 1993, 115, 9347-9348.
42. Chen, D. J.; Chen, Z. C. Tetrahedron Lett 2000, 41, 7361-7363.
43. Li, X.-Q.; Zhao, X.-F.; Zhang, C. Synthesis 2008, 2589-2593.
44. Tohma, H.; Egi, M.; Ohtsubo, M.; Watanabe, H.; Takizawa, S.; Kita, Y. Chem Commun 1998, 173-174.
45. Kita, Y.; Tohma, H.; Inagaki, M.; Hatanaka, K.; Yakura, T. Tetrahedron Lett 1991, 32, 4321-4324.
46. Kita, Y.; Tohma, H.; Takada, T.; Mitoh, S.; Fujita, S.; Gyoten, M. Synlett 1994, 427-428.
47. Zhdankin, V. V.; Hanson, K. J.; Koposov, A. E.; Blomquist, E.; Tykwinski, R. R. Mendeleev Commun 2001, 51-52.
48. Krasutsky, A. P.; Kuehl, C. J.; Zhdankin, V. V. Synlett 1995, 1081-1082.
49. Zhdankin, V. V.; Krasutsky, A. P.; Kuehl, C. J.; Simonsen, A. J.; Woodward, J. K.; Mismash, B.; Bolz, J. T. J Am Chem Soc 1996, 118, 5192-5197.
50. Cech, F.; Zbiral, E. Tetrahedron 1975, 31, 605-612.
51. Tingoli, M.; Tiecco, M.; Chianelli, D.; Belducci, R.; Temperini, A. J Org Chem 1991, 56, 6809-6813.
52. Fontana, F.; Minisci, F.; Yan, Y. M.; Zhao, L. Tetrahedron Lett 1993, 34, 2517-2520.
53. Pedersen, C. M.; Marinescu, L. G.; Bols, M. Org Biomol Chem 2005, 3, 816-822.
54. Braese, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew Chem Int Ed 2005, 44, 5188-5240.
55. Tasset, G.; Smets, G. J Polym Sci 1954, 12, 517-531.
56. Watanabe, O.; Tabata, M.; Sohma, J. Polym Degrad Stab 1984, 7, 13-24.
57. Guyot, A. Polym Degrad Stab 1986, 15, 219-235.
58. Gurst, J. E. In The Chemistry of the Azido Group; Patai, S., Ed.; Interscience: London, 1971; pp 191-202.
59. Lieber, E.; Rao, C. N. R.; Chao, T. S.; Hoffman, C. W. W. Anal Chem 1957, 29, 916-918.
60. Carpenter, W. R. Appl Spectrosc 1963, 17, 70-72.
61. Balderman, D.; Kalir, A. Synthesis 1978, 24-26.
62. Kornblum, N.; Ackermann, P.; Manthey, J. W.; Musser, M. T.; Pinnick, H. W.; Singaram, S.; Wade, P. A. J Org Chem 1988, 53, 1475-1481.
63. Young, C. W.; DuVall, R. B.; Wright, N. Anal Chem 1951, 23, 709-714.
64. Claridge, T. D. W. High-Resolution NMR Techniques in Organic Chemistry, 2nd ed.; Elsevier: Oxford, 2009.
65. Golas, P. L.; Tsarevsky, N. V.; Matyjaszewski, K. Macromol Rapid Commun 2008, 29, 1167-1171.
66. Mueller, J. Z Naturforsch B 1979, 34, 437-441.
67. Siemsen, P.; Livingston, R. C.; Diederich, F. Angew Chem Int Ed 2000, 39, 2632-2657.
68. Duxbury, C. J.; Cummins, D.; Heise, A. J. Polym Sci Part A: Polym Chem 2009, 47, 3795-3802.
69. Bang, J.; Bae, J.; Loewenhielm, P.; Spiessberger, C.; Given-Beck, S. A.; Russell, T. P.; Hawker, C. J. Adv Mater 2007,19,4552-4557.
70. Al Akhrass, S.; Ostaci, R.-V.; Grohens, Y.; Drockenmuller, E.; Reiter, G. Langmuir 2008, 24, 1884-1890.
71. Al Akhrass, S.; Gal, F.; Damiron, D.; Alcouffe, P.; Hawker, C. J.; Cousin, F.; Carrot, G.; Drockenmuller, E. Soft Matter 2009, 5, 586-592.