Generation of alkoxyl radicals from N-alkoxy-2-pyridones

Bulletin of the Korean Chemical Society

Volumn 26, Issue 11, 2005, Pages 1869-1871

  Kim, Eunae ^a   Chang, Ho Cho ^a   Kim, Sunggak ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

Alcohol; Alkoxyl radical; N Alkoxy 2 pyridone; Radical

Indexed keywords

EID: 31744433328     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2005.26.11.1869     Document Type: Article

References (43)

1. (a) Kochi, J. In Free Radicals; Kochi, J., Ed.; Wiley: New York, 1973; Vol. 2, Ch. 24.
2. (b) Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980; Vol. 1, pp 161-309.
3. (c) Ramaiah, M. Tetrahedron 1987, 43, 3541.
4. (d) Suarez, E.; Rodriguez, M. S. Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 440-454, Ch. 5.3.
5. (e) Hartung, J.; Gottwald, T.; Spehar, K. Synthesis 2002, 1469.
6. (f) Kim, S.; Cho, C. H.; Lim, C. J. J. Am. Chem. Soc. 2003, 125, 9574.
7. (a) Majetich, G.; Wheless, K. Tetrahedron 1995, 51, 7095.
8. (b) Feray, L.; Kuznetsov, N.; Renaud, P. Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 246-278, Ch. 3.6.
9. (c) Cekovic, Z. Tetrahedron 2003, 59, 8073.
10. (a) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1960, 82, 2640.
11. (b) Akhtan, M. Adv. Photochem. 1964, 2, 263.
12. (a) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925.
13. (b) Vite, G. D.; Fraser-Reid, B. Synth. Commun. 1988, 18, 1339.
14. (a) Kraus, G. A.; Thurston, J. Tetrahedron Lett. 1987, 28, 4011.
15. (b) Furuta, K.; Nagata, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 2215.
16. (c) Suginome, H.; Wang, J. B. J. Chem. Soc., Perkin Trans. 1 1990, 2825.
17. (d) Inanaga, J.; Sugimoto, Y.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1992, 33, 8109.
18. (a) Beckwith, A. L. J.; Hay, B. P.; Williams, G. M. J. Chem. Soc., Chem. Commun. 1989, 1202.
19. (b) Pasto, D. J.; L'Hermine, G. J. Org. Chem. 1990, 55, 5815.
20. (c) Pasto, D. J.; Cottard, F. Tetrahedron Lett. 1994, 35, 4303.
21. (a) Kim, S.; Lee, T. A.; Song, Y. Synlett 1998, 471.
22. (b) Crich, D.; Huang, X.; Newcomb, M. Org. Lett. 1999, 1, 225.
23. (c) Crich, D.; Huang, X.; Newcomb, M. J. Org. Chem. 2000, 65, 523.
24. For other alkoxyl radical precursors, see: (a) Hartung, J. Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 427-439, Ch. 5.2.
25. (b) Kim, S.; Lee, T. A. Synlett 1997, 950.
26. (c) Kim, S.; Lim, C. J.; Song, S.-E.; Kang, H.-Y. Synlett 2001, 688.
27. (d) Hartung, J.; Thomas, G.; Kristina, S. Synlett 2003, 227.
28. (a) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1988, 110, 4415.
29. (b) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 111, 230.
30. Hay, B. P.; Beckwith, A. L. J. J. Org. Chem. 1989, 54, 4330.
31. (a) Hartung, J. Synlett 1996, 1206.
32. (b) Hartung, J.; Kneuer, R.; Schwarz, M.; Svoboda, I.; Fueb, H. Eur. J. Org. Chem. 1999, 97.
33. (c) Hartung, J. Eur. J. Org. Chem. 2001, 619.
34. (a) Adam, W.; Marquardt, S.; Kemmer, D.; Saha-Moller, C. R.; Schreier, P. Photochem. Photobiol. Sci. 2002, 1, 609.
35. (b) Adam, W.; Hartung, J.; Okamoto, H.; Marquardt, S.; Nau, W. M.; Pischel, U.; Saha-Moller, C. R.; Spehar, K. J. Org. Chem. 2002, 67, 6041.
36. (a) Sakurai, T.; Kubo, K.; Kojima, S.; Shoro, T.; Inoue, H. Tetrahedron Lett. 1998, 39, 9747.
37. (b) Yoshioka, N.; Andoh, C.; Kubo, K.; Igarashi, T.; Sakurai, T. J. Chem. Soc., Perkin Trans. 2 2001, 1927.
38. Barton, D. H. R.; Blundell, P.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1989, 30, 2341.
39. For our recent reports, (a) Kim, S.; Lim, C. J. Bull. Korean Chem. Soc. 2003, 24, 1219.
40. (b) Lee, S.; Lim, C. J.; Kim, S. Bull. Korean Chem. Soc. 2004, 25, 1611.
41. (a) Katritzky, A. R. J. Chem. Soc. 1957, 191.
42. (b) Gardner, J. N.; Katritzky, A. R. J. Chem. Soc. 1957, 4375.
43. (c) Paquette, L. A. J. Am. Chem. Soc. 1965, 87, 5186.