Substituent effects on regioselectivity in the autoxidation of nonconjugated dienes

Journal of the American Chemical Society

Volumn 131, Issue 15, 2009, Pages 5635-5641

  Tallman, Keri A ^a   Rector, Christopher L ^a   Porter, Ned A ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIENE STRUCTURES; FATTY ACID ESTERS; FREE RADICAL OXIDATION; HYDROPEROXIDE; HYDROPEROXIDES; KINETIC PRODUCT; NONCONJUGATED; OXYGEN ADDITION; PENTADIENYL; PEROXYL RADICAL; PRODUCT DISTRIBUTIONS; RADICAL REACTIONS; STERIC HINDRANCES; SUBSTITUENT EFFECT; TOCOPHEROL CONCENTRATION; VARIABLE CONCENTRATION;

ESTERS; FATTY ACIDS; OXYGEN; REACTION KINETICS; REGIOSELECTIVITY;

OXIDATION;

ALKADIENE; ALPHA TOCOPHEROL; FREE RADICAL; HYDROPEROXIDE DERIVATIVE; OMEGA 3 FATTY ACID; OMEGA 6 FATTY ACID; OXYGEN; ALKENE; HYDROGEN PEROXIDE; OXIDIZING AGENT;

ARTICLE; AUTOOXIDATION; CHEMICAL STRUCTURE; OXIDATION; RADICAL REACTION; SYNTHESIS; CHEMISTRY; OXIDATION REDUCTION REACTION;

ALKENES; ALPHA-TOCOPHEROL; FATTY ACIDS, OMEGA-3; FATTY ACIDS, OMEGA-6; FREE RADICALS; HYDROGEN PEROXIDE; OXIDANTS; OXIDATION-REDUCTION;

EID: 67849099354     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja900040d     Document Type: Article

References (43)

1. (a) Porter, N. A. Acc. Chem. Res. 1986, 19, 262-268.
2. (b) Porter, N. A.; Caldwell, S. E.; Mills, K. A. Lipids 1995, 30, 277-290.
3. (a) Steinburg, D.; Parhsarathy, S.; Carew, T. E.; Khoo, J. C.; Witztum, J. L. N. Engl. J. Med 1989, 320, 915-924.
4. (b) Chisholm, G. M.; Steinburg, D. Free Radical Biol. Med. 2000, 28, 1815-1826.
5. Montine, K. S.; Quinn, J. F.; Zhang, J.; Fessel, J. P.; Roberts, L. J.; Morrow, J. D.; Montine, T. J. Chem. Phys. Lipids 2004, 128, 117-124, 2004.
6. (a) Marnett, L. J. Carcinogenesis 2000, 21, 361-370.
7. (b) Sevanian, A.; Ursini, F. Free Radical Biol. Med. 2000, 29, 306-311.
8. (c) Spiteller, G.; Spiteller, D.; Jira, W.; Kiessling, U.; Dudda, A.; Weisser, M.; Hecht, S.; Schwarz, C. Peroxide Chem. 2000, 179-208.
9. Tallman, K. A.; Roschek, B., Jr.; Porter, N. A. J. Am. Chem. Soc. 2004, 126, 9240.
10. (a) Sargis, R. M.; Subbaiah, P. V. Biochemistry 2003, 42, 11533.
11. (b) Katan, M. B.; Zock, P. L.; Mensink, R. P. Annu. Rev. Nutr. 1995, 15, 473.
12. (c) Mensink, R. P.; Katan, M. B. New Engl. J. Med. 1990, 323, 439.
13. Pratt, D. A.; Mills, J. H.; Porter, N. A. J. Am. Chem. Soc. 2003, 125, 5801.
14. Frankel, E. N.; Garwood, R. F.; Vinson, J. R.; Weedon, B. C. L. J Chem. Soc. Perkin Trans. 1 1982, 2707.
15. Ivanov, I. V.; Groza, N. V.; Romanov, S. G.; Kühn, H.; Myagkova, G. I. Synthesis 2000, 691.
16. (a) Dasse, O.; Mahadevan, A.; Han, L.; Martin, B. R.; Di Marzo, V.; Razdan, R. K. Tetrahedron 2000, 56, 9195.
17. (b) Jeffery, T.; Gueugnot, S.; Linstrumelle, G. Tetrahedron Lett. 1992, 33, 5757.
18. (a) Brash, A. R. Lipids 2000, 35, 947.
19. (b) Tallman, K. A.; Pratt, D. A.; Porter, N. A. J. Am. Chem. Soc. 2001, 123, 11827.
20. (c) Roschek, B., Jr.; Tallman, K. A.; Rector, C. L.; Gillmore, J. G.; Pratt, D. A.; Punta, C; Porter, N. A. J. Org. Chem. 2006, 71, 3527.
21. Punta, C.; Rector, C. L.; Porter, N. A. Chem. Res. Toxicol. 2005, 18, 349.
22. The products of γ-linolenate have been previously identified as described in ref 12. a-Linolenate oxidation products have also been described. Chan, H. W.-S.; Levett, G. Lipids 1977, 12, 837.
23. (a) MacPhee, J. A.; Panaye, A.; Dubois, J.-E. Tetrahedron Lett. 1978, 19, 3293.
24. (b) Shorter, J. Advances in Linear Free Energy Relationships; Chapman, N. B.; Shorter, J., Eds.; Plenum Press: London, 1972; Chapter 2.
25. (c) Anslyn, E.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science Books: Mill Valley, CA, 2006; p 104.
26. (a) Tidwell, T. Tetrahedron 1978, 34, 1855.
27. (b) Ermer, O.; Lifson, S. Tetrahedron 1974, 30, 2425.
28. (a) Bascetta, E.; Gunstone, F. D.; Scrimgeour, C. M.; Walton, J. C. J. Chem. Soc, Chem. Commun. 1982, 110.
29. (b) Bascetta, E.; Gunstone, F. D.; Walton, J. C. J. Chem. Soc, Perkin Trans. 2 1983, 603.
30. (a) Mills, K. A.; Caldwell, S. E.; Dubay, G. R.; Porter, N. A. J. Am. Chem. Soc. 1992, 114, 9689.
31. (b) Porter, N. A.; Mills, K. A.; Carter, R. L. J. Am. Chem. Soc. 1994, 116, 6690.
32. (c) Porter, N. A.; Mills, K. A.; Caldwell, S. E.; Dubay, G. R. J. Am. Chem. Soc. 1994, 116, 6697.
33. (d) Lowe, J. R.; Porter, N. A. J. Am. Chem. Soc. 1997, 119, 11534.
34. Previous studies have ruled out the intermediacy of the cyclic 1,2-dioxolanyl-4-yl radical. (a) Brill, W. F. J. Chem. Soc, Perkin Trans. 2 1984, 621.
35. (b) Porter, N.; Zuraw, P. J. Chem. Soc, Chem. Commun. 1985, 1472.
36. (c) Porter, N. A.; Wujek, J. S. J. Org. Chem. 1987, 52, 5085.
37. (d) Boyd, S. L.; Boyd, R. J.; Shi, Z.; Barclay, R. C.; Porter, N. A. J. Am. Chem. Soc. 1993, 115, 687.
38. Olivella, S.; Solé, A. J. Am Chem. Soc. 2003, 125, 10641.
39. (a) Porter, N. A.; Lehman, L. S.; Weber, B. A.; Smith, K. J. J. Am. Chem. Soc. 1981, 103, 6447.
40. (b) Porter, N. A.; Wujek, D. G. J. Am. Chem. Soc. 1984, 106, 2626.
41. Coates, R. M.; Firsan, S. J. J. Org. Chem. 1986, 51, 5198.
42. BHT radicals do not propagate the oxidative chain, whereas tocopheryl radicals may do so. Bowry, V. W.; Stocker, R. J. Am. Chem. Soc. 1993, 115, 6029.
43. Chan, H. W.-S.; Levett, G. Lipids 1977, 12, 837.