Carbon radicals of low reactivity against oxygen: Radically different antioxidants

Angewandte Chemie - International Edition

Volumn 46, Issue 28, 2007, Pages 5274-5276

  Korth, Hans Gert ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

Antioxidants; Autoxidation; Homolysis; Peroxides; Radicals

Indexed keywords

AUTOXIDATION; HOMOLYSIS; RADICALS;

DIMERS; MOLECULAR OXYGEN; PEROXIDES; REACTION KINETICS;

CARBON;

EID: 34447570834     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701569     Document Type: Review

References (25)

1. K. U. Ingold, Acc. Chem. Res. 1969, 2, 1-9.
2. N. Porter, Acc. Chem. Res. 1986, 19, 262-268.
3. J. Pokorny, N. Yanishlieva, M. Gordon, Antioxidants in Foods, Woodhead Publishing, Cambridge, 2001.
4. R. M. Mortier, S. T. Orszulik, Chemistry and Technology of Lubricants, Blackie Academic & Professional, London, 1997.
5. H. Zweifel, Stabilization of Polymeric Materials, Springer, Berlin, 1997.
6. B. Halliwell, J. M. C. Gutteridge, Free Radicals in Biology and Medicine, 4rd ed., Oxford University Press, New York, 2004.
7. F. Shahidi, Natural Antioxidants: Chemistry, Health Effects, and Applications, The American Oil Chemist's Society, Champaign, IL, 1997.
8. G. W. Burton, K. U. Ingold, Acc. Chem. Res. 1986, 19, 194-201.
9. E. Niki, N. Noguchi, Acc. Chem. Res. 2004, 37, 45-51.
10. M. B. Davies, J. Austin, D. A. Partridge, Vitamin C: Its Chemistry and Biochemistry, The Royal Society of Chemistry, Cambridge, 1991.
11. J. A. Howard, in Peroxyl Radicals (Ed.: Z. B. Alfassi), Wiley, Chichester, 1997, p. 283.
12. P. Mulder, H.-G. Korth, K. U. Ingold, Helv. Chim. Acta 2005, 88, 370-374.
13. M. Frenette, P. MacLean, L. R. C. Barclay, J. C. Scaiano, J. Am. Chem. Soc. 2006, 128, 16 432-16 434.
14. P. Nesvadba, S. Evans, C. Kröhnke, J. Zingg, Ger. Offen. 4432732, 1995.
15. H. S. Laver, P. Nesvadba, Eur Pat. Appl. 857765, 1998.
16. J. C. Scaiano, A. Martin, G. P. A. Yap, K. U. Ingold, Org. Lett. 2000, 2, 899-901.
17. M. Gomberg, J. Am. Chem. Soc. 1900, 22, 757-771.
18. E. Font-Sanchis, C. Aliaga, K.-S. Focsaneanu, J. C. Scaiano, Chem. Commun. 2002, 1576-1577.
19. M. Frenette, C. Aliaga, E. Font-Sanchis, J. C. Scaiano, Org. Lett. 2004, 6, 2579-2582.
20. The dimer of the triphenylmethyl radical is best known as the "head-to-tail" dimer, a cyclohexadienyl derivative, rather than the "head-to-head" dimer hexaphenyl ethane; see: H. Lankamp, W. T. Nauta, C. MacLean, Tetrahedron Lett. 1968, 1249-1254.
21. H. Wieland, Chem. Ber. 1911, 44, 2550-2556.
22. K.-S. Focsaneanu, C. Aliaga, J. C. Scaiano, Org. Lett. 2005, 7, 4979-4982.
23. L. R. C. Barclay, Can. J. Chem. 1993, 71, 1-16.
24. G. W. Burton, T. Doba, J. E. Gabe, L. Hughes, F. L. Lee, L. Prasad, K. U. Ingold, J. Am. Chem. Soc. 1985, 107, 7053-7065.
25. D. W. Snelgrove, J. Lusztyk, J. Banks, P. Mulder, K. U. Ingold, J. Am. Chem. Soc. 2001, 123, 469-477.