A new and efficient heterogeneous system for the phthalimide N-oxyl (PINO) radical generation

European Journal of Organic Chemistry

Volumn , Issue 11, 2007, Pages 1725-1729

  Coseri, Sergiu ^a  

^a PETRU PONI INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Romania)

Author keywords

Heterogeneous catalysis; NHPI; Oxidation; PINO; Radical reactions

Indexed keywords

EID: 34250684235     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601072     Document Type: Article

References (48)

1. a) Y. Ishii, K. Nakayama, M. Takeno, S. Sakaguchi, T. Iwahama, Y. Nishiyama, J. Org. Chem. 1995, 60, 3934-3935;
2. b) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal. 2001, 343, 393-427.
3. Y. Ishii, T. Iwahama, S. Sakaguchi, K. Nakayama, M. Takeno, Y. Nishiyama, J. Org. Chem. 1996, 61, 4520-4526.
4. a) Y. Yoshino, Y. Hayashi, T. Iwahama, S. Sakaguchi, Y. Ishii, J. Org. Chem. 1997, 62, 6810-6813;
5. b) B. B. Wentzel, M. P. J. Donners, P. L. Alsters, M. C. Feiters, R. J. M. Nolte, Tetrahedron 2000, 56, 7797-7803.
6. a) T. Iwahama, Y. Yoshima, T. Keitoku, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2000, 65, 6502-6507;
7. b) F. Minisci, C. Punta, F. Recupero, F. Fontana, G. F. Pedulli, Chem. Commun. 2002, 7, 688-689.
8. A. Cecchetto, F. Minisci, F. Recupero, F. Fontana, G. F. Pedulli, Tetrahedron Lett. 2002, 43, 3605-3607.
9. F. Minisci, C. Punta, F. Recupero, F. Fontana, G. F. Pedulli, J. Org. Chem. 2002, 67, 2671-2676.
10. E. Grochowski, T. Boleslawska, J. Jurezak, Synthesis 1977, 718.
11. A. Mackor, T. A. J. W. Wajer, T. de Boer, Tetrahedron 1968, 24, 1623.
12. a) T. Iwahama, K. Syojyo, S. Sakaguchi, Y. Ishii, Org. Process Res. Dev. 1998, 2, 255-260;
13. b) S. Sakaguchi, Y. Nishiwaki, T. Kitamura, Y. Ishii, Angew. Chem. Int. Ed. 2001, 40, 222-224.
14. a) F. Minisci, F. Recupero, G. F. Pedulli, M. Lucarini, J. Mol. Catal. A 2003, 204-205, 63-90;
15. b) C. Ueda, M. Noyama, H. Ohmori, M. Masui, Chem. Pharm. Bull. 1987, 35, 1372-1377;
16. c) N. Koshino, Y. Cay, J. H. Espenson, J. Phys. Chem. A 2003, 107, 4262-4267;
17. d) N. Koshino, B. Sana, J. H. Espenson, J. Org. Chem. 2003, 68, 9364-9370.
18. M. Masui, T. Ueshima, S. Ozaki, J. Chem. Soc., Chem. Commun. 1983, 479-480.
19. Y. Ishii, J. Mol. Catal. A 1997, 117, 123-137.
20. T. Iwahama, S. Sakaguchi, Y. Nishiyama, Y. Ishii, Tetrahedron Lett. 1995, 36, 6923-6926.
21. Y. Ishii, S. Sakaguchi, Catal. Surveys Jpn. 1999, 3, 27-35.
22. S. Mukhopadhyay, S. B. Chandalia, Org. Proc. Res. Dev. 1999, 3, 227-231.
23. D. D. Davis in Ullman's Encyclopedia of Industrial Chemistry, 5th ed., vol. A27 (Ed.: W. Gerhartz), VCH, Weinheim, 1985, p. 584.
24. C. Einhorn, J. Einhorn, C. Marcadal, J.-L. Pierre, Chem. Commun. 1997, 447-448.
25. A. Calder, A. R. Forrester, R. H. Thomson, J. Chem. Soc. C 1969, 512-516.
26. P. Baiocco, A. M. Barreca, M. Fabrini, C. Galli, P. Gentili, Org. Biomol. Chem. 2003, 1, 191-197.
27. G. Yang, Q. Zhang, H. Miao, X. Tong, J. Xu, Org. Lett. 2005, 7, 263-266.
28. S. Coseri, K. U. Ingold, Org. Lett. 2004, 6, 1641-1643.
29. S. Coseri, G. D. Mendenhall, K. U. Ingold, J. Org. Chem. 2005, 70, 4629-4636.
30. R. Amorati, M. Lucarini, V. Mugnaini, G. F. Pedulli, F. Minisci, F. Recupero, F. Fontana, P. Astolfi, L. Greci, J. Org. Chem. 2003, 68, 1747-1754.
31. E. Lemaire, A. Rassat, Tetrahedron Lett. 1964, 5, 2245-2248.
32. N. Koshino, Y. Cai, J. H. Espenson, J. Phys. Chem. A 2003, 107, 4262-4267.
33. Y. Cai, N. Koshino, B. Saha, J. H. Espenson, J. Org. Chem. 2005, 70, 238-243.
34. K.-D. Gundermann, L. Schwandt, Houben-Weil, 4th ed., vol. E3 (Ed.: J. Falbe), Georg Thieme Verlag, Stuttgart, 1983, p. 510.
35. H. O. House, Modern Synthetic Reactions, W. A. Benjamin Inc., Menlo Park, CA, 1972, p. 353.
36. A. K. Qureshi, B. Sklarz, J. Chem. Soc. C 1966, 412-415.
37. G. E. Keck, S. A. Fleming, Tetrahedron Lett. 1978, 19, 4763-4766.
38. E. Santaniello, F. Ponti, A. Manzocchi, Tetrahedron Lett. 1980, 21, 2655-2656.
39. P. S. Kalsi, P. P. Kam, J. Singh, B. Chhabra, Chem. Ind. (London) 1987, 394.
40. A. McKillop, D. N. Young, Synthesis 1979, 401-422.
41. A. Akelah, D. C. Sherrington, Polymer 1983, 24, 1369-1386.
42. V. Krchnak, G. A. Slough, Tetrahedron Lett. 2004, 45, 5237-5241.
43. V. Krchnak, J. Comb. Chem. 2005, 7, 507-509.
44. V. Krchnak, J. Zajicek, J. Comb. Chem. 2005, 7, 523-525.
45. K. J. Stanger, V. Krchnak, J. Comb. Chem. 2006, 8, 435-439.
46. D. N. Gupta, P. Hodge, J. E. Davies, J. Chem. Soc., Perkin Trans. 1 1981, 2970-2973.
47. F. Huet, A. Lechevallier, M. Pellet, J. M. Konia, Synthesis 1978, 63-64.
48. M. Hoto, R. Matsuda, Tetrahedron Lett. 1976, 17, 613-614.