Hydrogen-transfer reactions from phenols to TEMPO prefluorescent probes in micellar systems

Organic Letters

Volumn 10, Issue 11, 2008, Pages 2147-2150

  Aliaga, Carolina ^a   Juárez Ruiz, Juan M ^b   Scaiano, J C ^b   Aspée, Alexis ^a  

^a UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

^b UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE OXIDE; ANTIOXIDANT; FLUORESCENT DYE; HYDROGEN; NITROGEN OXIDE; PHENOL DERIVATIVE; TEMPO;

ARTICLE; CHEMISTRY; FLUORESCENCE; KINETICS; MICELLE;

ANTIOXIDANTS; CYCLIC N-OXIDES; FLUORESCENCE; FLUORESCENT DYES; HYDROGEN; KINETICS; MICELLES; NITROGEN OXIDES; PHENOLS;

EID: 52649099049     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800446c     Document Type: Article

References (29)

1. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine; Oxford University Press: Oxford, 1999.
2. Valgimigli, L.; Banks, J. T.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1995, 117, 9966-9971.
3. Burton, G. W.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 6472-6477.
4. Litwinienko, G.; Ingold, K. U. J. Org. Chem. 2004, 69, 5888-5896.
5. Burton, G. W.; Ingold, K. U. Acc. Chem. Res. 1996, 19, 194-201.
6. Aliaga, C.; Aspée, A.; Scaiano, J. C. Org. Lett. 2003, 5, 4145-4148.
7. Blough, N. V.; Simpson, D. J J. Am. Chem. Soc. 1988, 110, 1915-1917.
8. Green, S. A.; Simpson, D. J.; Zhou, G.; Ho, P. S.; Blough, N. V. J. Am. Chem. Soc. 1990, 112, 7337-7346.
9. Coenjarts, C.; García, O.; Llauger, L.; Palfreyman, J.; Vinette, A. L.; Scaiano, J. C. J. Am. Chem. Soc. 2003, 125, 620-621.
10. Burton, G. W.; Doba, T.; Gabe, E.; Hughes, L.; Lee, F. L.; Pasad, L.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 7053-7065.
11. Zhou, B.; Wu, L. M.; Liu, Z. L. Free Radic. Biol. Med. 2005, 38, 78-84.
12. Valgimigli, L.; Banks, J. T.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1995, 117, 9966-9971.
13. Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4983-4992.
14. Fuguet, E.; Ràfols, C.; Rosés, M.; Bosch, E. Anal. Chim. Acta 2005, 548, 95-100.
15. Patist, A.; Chhabra, V.; Pagidipati, R.; Shah, R.; Shah, D. O. Langmuir 1997, 13, 432-434.
16. Aspée, A.; Aliaga, C.; Scaiano, J. C. Photochem. Photobiol. 2007, 83, 481-485.
17. Jovanovic, S. V.; Steenken, S.; Tosic, M.; Marjanovic, B.; Simic, M. G. J. Am. Chem. Soc. 1994, 116, 4846-4851.
18. Sauerwald, N.; Schwenk, M.; Polster, J.; Bengsch, E. Z. Naturforsch. 1998, 53b, 315-321.
19. Jovanovic, S. V.; Steenken, S.; Hara, Y.; Simic, M. G. J. Chem. Soc., Perkin Trans. 2 1996, 2497-2504.
20. Kato, Y.; Simizu, Y.; Yijing, L.; Unoura, K.; Utsumi, H.; Ogata, T. Electrochim. Acta 1995, 40, 2799-2802.
21. Pérez, D. D.; Leighton, F.; Aspée, A.; Aliaga, C.; Lissi, E. A. Biol. Res. 2000, 33, 71-77.
22. Aliaga, C.; Lissi, E. A. Can. J. Chem. 2004, 82, 1668-1673.
23. Medvedeva, N.; Martin, V. V.; Weis, A. L.; Likhteinshten, G. I. J. Photochem. Photobiol. A 2004, 163, 45-51.
24. López-Alarcón, C.; Aspée, A.; Lissi, A Food Chem. 2007, 104, 1430-1435.
25. López-Alarcón, C.; Lissi, E. A. Free Rad. Res. 2005, 39, 729-736.
26. Aspée, A.; García, O.; Maretti, L.; Sastre, R.; Scaiano, J. C. Macromolecules 2003, 36, 3550-3556.
27. Blinco, J. P.; McMurtrie, J. C.; Bottle, S. E. Eur. J. Org. Chem. 2007, 4638-4641.
28. Micallef, A. S.; Blinco, J. P.; George, G. A.; Reid, D. A.; Rizzardo, E.; Thang, S. H.; Bottle, S. E. Polym. Degrad. Stab. 2005, 89, 427-435.
29. Fairfull-Smith, K. E.; Blinco, J. P.; Keddie, D. J.; George, G. A.; Bottle, S. E Macromolecules 2008, 41, 1577-1580.