PolyHIPEs as novel media for conventional free radical chemistry

Letters in Organic Chemistry

Volumn 5, Issue 4, 2008, Pages 304-307

  Zhang, Shengmiao ^a   Chen, Jianding ^a   Perchyonok, Victoria Tamara ^b  

^a East China University of Science and Technology   (China)

^b MONASH UNIVERSITY   (Australia)

Author keywords

Free radicals; Green chemistry; PolyHIPEs as reaction media; Synthesis

Indexed keywords

EID: 50249166679     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017808784049443     Document Type: Article

References (30)

1. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press, Oxford, 1986 and references sited there in.
2. Motherwell, W.; Crich, D. Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1992 and references sited there in.
3. (a) Chen, L.; Li, C.-J. Adv. Synth. Catal., 2006, 348, 1459;
4. (b) Li, C.-J. Chem. Rev., 2005, 105, 3095;
5. (c) Lindstrom, U. M. Chem: Rev., 2002, 102, 2751.
6. For reviews on stereoselective radical reactions, see (a) Bar, G.; Parson, A. Chem. Soc. Rev., 2003, 32, 251;
7. (b) Guerin, B.; Ogilvie, W.W.; Guindon, Y. in Radicals in Organic Synthesis ed. Renaud, P.; Sibi, M. P. Wiley-VCH, Wenheim, 2001, vol. 1;
8. (c) Curran, D.P.; Porter, N. A,; Giese, B. Stereochemistry of Radical Reactions, VCH, Weinheim, 1996.
9. For reviews on enantioselective radical reactions and Lewis acid catalyzed radical reactions, see (a) Sibi, M. P.; Manyen, S.; Zimmerman, J. Chem. Rev., 2003, 103, 3263;
10. (b) Sibi, M. P.; Porter, N. A. Acc. Chem. Res., 1999, 32, 163;
11. (c) Renaud, P.; Gerster, M. Angew. Chem. Int. Ed., 1998, 37, 2562.
12. For an example using hydrogen bond interactions, see Aechtner, T.; Dressel, M.; Bach, T. Angew. Chem. Int. Ed., 2004, 43, 5849.
13. For examples of stereoselective radical additions to C=N bonds see (a) Singh, N.; Anand, R. D.; Trehan, S. T. Tetrahedron Lett., 2004, 45, 2911;
14. (b) Friestad, G. K.; Shen, W.; Ruggles, E. L. Angew. Chem. Int. Ed., 2003, 42, 5061;
15. (c) Miyabe, H.; Ushiro, C.; Ueda, M.; Yamakawa, K.; Naito, T. J. Org. Chem., 2000, 65, 176;
16. (d) Holland, N.; Jorgensen, K. A. J. Chem. Soc. Perkin Trans. 1, 2001, 1290;
17. (e) Yamamoto, Y.; Ito, W. Tetrahedron, 1988, 44, 5415.
18. (a) Barbetta, A.; Dentini, M.; De Vecchis, M. S.; Filippini, P.; Formisano, G.; Caiazza, S. Adv. Funct. Mater., 2005, 15, 118;
19. (b) J. Pierre, S.; Thies, J. C.; Dureault, A.; Cameron, N. R.; van Hest, J. C. M.; Carette, N.; Michon, T.; Weberskirch, R. Adv. Mater., 2006, 18, 1822;
20. (c) Wakeman, R. J.; Bhumgara, Z. G.; Akay, G. Chem. Eng. J., 1998, 70, 133.
21. Myers, D. Surfactant Science and Technology. 3rd ed. New Jersey: John Wiley and Sons, 2006, 291.
22. (a) Cameron, N. R. Polymer, 2005, 46, 1439; (b) Krajnc, P.; Brown, J. F.; Cameron, N. R. Org. Lett., 2002, 4, 2497.
23. Zhang, S.; Chen, J. Polymer, 2007, 48, 3021.
24. Kita, Y.; Nambu, H.; Ramesh, N. G.; Anikumar, G.; Matsugi, M. Org. Lett., 2001, 3, 1157.
25. Jang, D.O.; Cho, D.Y. Synlett, 2002, 1523.
26. Jang, D.O.; Cho, D.Y. Tetrahedron Lett., 2002, 43, 5921.
27. Jang, D.O.; Cho, D.Y. Synlett, 2002, 631.
28. Kita, Y.; Nambu, H.; Ramesh, N. G.; Anikumar, G.; Matsugi, M. Org. Lett., 2001, 3, 1157.
29. Cho, D. H.; Jang, D. O. Chem. Comm., 2006, 48, 5045.
30. Baguley, P.A.; Walton, J.C. Angew. Chem. Int. Ed., 1998, 37, 3073.