Synthesis of a kinetically stabilized homoditopic nitrile N-oxide directed toward catalyst-free click polymerization

Chemistry Letters

Volumn 39, Issue 4, 2010, Pages 420-421

  Lee, Young Gi ^a   Yonekawa, Morio ^a   Koyama, Yasuhito ^a   Takata, Toshikazu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77950826132     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2010.420     Document Type: Article

References (25)

1. a) H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem., Int. Ed. 2001, 40, 2004.
2. b) C. W. Tornoe, C. Christrasen, M. Meldal, J. Org. Chem. 2002, 67, 3057.
3. For a selected review, see: C. J. Hawker, K. L. Wooley, Science 2005, 309, 1200.
4. For selected reports of click polymerization exploiting Huisgen reaction, see: a) D. J. V. C. van Steenis, O. R. P. David, G. P. F. van Strijdonck, J. H. van Maarseveen, J. N. H. Reek, Chem. Commun. 2005, 4333.
5. b) J.-F. Lutz, Angew. Chem., Int. Ed. 2007, 46, 1018.
6. c) D. Fournier, R. Hoogenboom, U. S. Schubert, Chem. Soc. Rev. 2007, 1369.
7. d) J. Nicolas, G. Mantovani, D. M. Haddleton, Macromot. Rapid Commun. 2007, 28, 1083.
8. a) R. K. O'Reilly, M. J. Joralemon, C. J. Hawker, K. L. Wooley, Chem-Eur. J. 2006, 12, 6776.
9. b) O. Altintas, B. Yankul, G. Hizal, U. Tunca, J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 6458.
10. c) D. D. Diaz, K. Rajagopal, E. Strabie, J. Schneider, M. G. Finn, J. Am. Chem. Soc. 2006, 128, 6056.
11. d) S. R. Gondi, A. P. Vogt, B. S. Sumerlin, Macromolecules 2007, 40, 474.
12. K. E. Russell, J. Am. Chem. Soc. 1955, 77, 3487.
13. a) Y. Iwakura, S. Shiraishi, M. Akiyama, M. Yuyama, Bull. Chem. Soc. Jpn. 1968, 41, 1648.
14. b) Y. Iwakura, K. Uno, S.-J. Hong, T. Hongu, Polym. J. 1971, 2, 36.
15. c) S. J. Hong, Y. Iwakura, K. Uno, Polymer 1971, 12, 521.
16. d) T. Kanbara, T. Ishii, K. Hasegawa, T. Yamamoto, Polym. Bull. 1996, 36, 673.
17. e) S. Grecian, V. V. Fokin, Angew. Chem. 2008, 120, 8409.
18. f) I. Singh, Z. Zarafshani, J.-F. Lutz, F. Heaney, Macromolecules 2009, 42, 5411.
19. For selected review on isoxazoles, see: S. A. Lang, Y. I. Lin, in Comprehensive Heterocyclic Chemistry, ed. by A. R. Katritzky, C. W. Rees, Pergamon, Oxford, 2000, Vol.6, p. 1.
20. For a related our report of the click polymerization exploiting homoditopic nitrile oxides, see: a) Y. Koyama, M. Yonekawa, T. Takata, Chem. Lett. 2008, 37, 918.
21. b) Y. G. Lee, Y. Koyama, M. Yonekawa, T. Takata, Macromolecules 2009, 42, 7709.
22. c) Y. G. Lee, Y. Koyama, M. Yonekawa, T. Takata, Macromolecules 2009, submitted.
23. For selected reports of stable nitirile N-oxides, see: a) P. Beltrame, C. Veglio, M. Simonetta, J. Chem. Soc. B 1967, 867.
24. b) C. Grundmann, R. Richter, J. Org. Chem. 1968, 33, 476.
25. Supporting Information is available electronically on the CSJJournal Web site, http://www.csj.jp/journals/chem-lett/index.html.