-
1
-
-
0024603895
-
-
(a) Steinburg, D.; Parhsarathy, S.; Carew, T. E.; Khoo, J. C.; Witztum, J. L. New Engl. J. Med. 1989, 320, 915.
-
(1989)
New Engl. J. Med.
, vol.320
, pp. 915
-
-
Steinburg, D.1
Parhsarathy, S.2
Carew, T.E.3
Khoo, J.C.4
Witztum, J.L.5
-
4
-
-
0006789450
-
-
(d) Spiteller, G.; Spiteller, D.; Jira, W.; Kessling, U.; Dudda, A.; Weisser, M.; Hecht, S.; Schwarz, C. Peroxide Chem. 2000, 179.
-
(2000)
Peroxide Chem.
, pp. 179
-
-
Spiteller, G.1
Spiteller, D.2
Jira, W.3
Kessling, U.4
Dudda, A.5
Weisser, M.6
Hecht, S.7
Schwarz, C.8
-
8
-
-
0028959042
-
-
(c) Porter, N. A.; Caldwell, S. E.; Mills, K. A. Lipids 1995, 30, 277.
-
(1995)
Lipids
, vol.30
, pp. 277
-
-
Porter, N.A.1
Caldwell, S.E.2
Mills, K.A.3
-
11
-
-
0001219196
-
-
(a) Beckwith, A. L. J.; O'Shea, D. M.; Roberts, D. H. J. Am. Chem. Soc. 1986, 108, 6408.
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 6408
-
-
Beckwith, A.L.J.1
O'Shea, D.M.2
Roberts, D.H.3
-
12
-
-
0033798477
-
-
(b) Brash, A. R. Lipids 2000, 35, 947.
-
(2000)
Lipids
, vol.35
, pp. 947
-
-
Brash, A.R.1
-
13
-
-
3342994686
-
-
(c) Hamberg, M.; Su, C.; Oliw, E. J. Biol. Chem. 1998, 273, 1080.
-
(1998)
J. Biol. Chem.
, vol.273
, pp. 1080
-
-
Hamberg, M.1
Su, C.2
Oliw, E.3
-
14
-
-
0035965716
-
-
Tallman, K. A.; Pratt, D. A.; Porter, N. A. J. Am. Chem. Soc. 2001, 123, 11827.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 11827
-
-
Tallman, K.A.1
Pratt, D.A.2
Porter, N.A.3
-
16
-
-
0029102377
-
-
(b) Katan, M. B.; Zock, P. L.; Mensink, R. P. Annu. Rev. Nutr. 1995, 15, 473.
-
(1995)
Annu. Rev. Nutr.
, vol.15
, pp. 473
-
-
Katan, M.B.1
Zock, P.L.2
Mensink, R.P.3
-
18
-
-
0034127632
-
-
(a) Ivanov, I. V.; Groza, N. V.; Romanov, S. G.; Kühn, H.; Myagkova, G. I. Synthesis 2000, 691.
-
(2000)
Synthesis
, pp. 691
-
-
Ivanov, I.V.1
Groza, N.V.2
Romanov, S.G.3
Kühn, H.4
Myagkova, G.I.5
-
19
-
-
0034680724
-
-
(b) Dasse, O.; Mahadevan, A.; Han, L.; Martin, B. R.; Di Marzo, V.; Razdan, R. K. Tetrahedron 2000, 56, 9195.
-
(2000)
Tetrahedron
, vol.56
, pp. 9195
-
-
Dasse, O.1
Mahadevan, A.2
Han, L.3
Martin, B.R.4
Di Marzo, V.5
Razdan, R.K.6
-
20
-
-
0026646344
-
-
(c) Jeffery, T.; Gueugnot, S.; Linstrumelle, G. Tetrahedron Lett. 1992, 33, 5757.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 5757
-
-
Jeffery, T.1
Gueugnot, S.2
Linstrumelle, G.3
-
21
-
-
0032867814
-
-
Brandsma, L.; Nieuwenhuizen, W. F.; Zwikker, J. W.; Mäeorg, U. Eur. J. Org. Chem. 1999, 775.
-
(1999)
Eur. J. Org. Chem.
, pp. 775
-
-
Brandsma, L.1
Nieuwenhuizen, W.F.2
Zwikker, J.W.3
Mäeorg, U.4
-
22
-
-
0037134189
-
-
Chun, J.; Li, G.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2002, 67, 2600.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 2600
-
-
Chun, J.1
Li, G.2
Byun, H.-S.3
Bittman, R.4
-
25
-
-
0033118519
-
-
(a) Bayer, E.; Gfrorer, P.; Rentel, C. Angew. Chem., Int. Ed. 1999, 38, 992.
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 992
-
-
Bayer, E.1
Gfrorer, P.2
Rentel, C.3
-
26
-
-
6844250104
-
-
(b) Suma, K.; Raju, N. P.; Vairamani, M. Rapid Commun. Mass Spectrom. 1997, 11, 1939.
-
(1997)
Rapid Commun. Mass Spectrom.
, vol.11
, pp. 1939
-
-
Suma, K.1
Raju, N.P.2
Vairamani, M.3
-
27
-
-
0034705975
-
-
(a) Havrilla, C. M.; Hachey, D. L.; Porter, N. A. J. Am. Chem. Soc. 2000, 122, 8042.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 8042
-
-
Havrilla, C.M.1
Hachey, D.L.2
Porter, N.A.3
-
28
-
-
0041346335
-
-
(b) Seal, J. R.; Havrilla, C. M.; Porter, N. A.; Hachey, D. L. J. Am. Soc. Mass Spectrom. 2003, 14, 872.
-
(2003)
J. Am. Soc. Mass Spectrom.
, vol.14
, pp. 872
-
-
Seal, J.R.1
Havrilla, C.M.2
Porter, N.A.3
Hachey, D.L.4
-
29
-
-
0000596187
-
-
Hock fragmentation is commonly observed in solution for lipid hydroperoxides and is promoted by protic or Lewis acids. (a) Hock, H. Angew. Chem. 1936, 49, 595.
-
(1936)
Angew. Chem.
, vol.49
, pp. 595
-
-
Hock, H.1
-
31
-
-
0007508451
-
-
(c) Tanigawa, S.; Kajiware, T.; Hatanaka, A. Phytochemistry 1984, 23, 2439.
-
(1984)
Phytochemistry
, vol.23
, pp. 2439
-
-
Tanigawa, S.1
Kajiware, T.2
Hatanaka, A.3
-
33
-
-
0030008434
-
-
1H NMR analysis and comparison to published spectra for similar compounds (cholesteryl linoleate), Kenar, J. A.; Havrilla, C. M.; Porter, N. A.; Guyton, J. R.; Brown, S. A.; Klemp, K. F.; Selinger, E. Chem. Res. Toxicol. 1996, 9, 737.
-
(1996)
Chem. Res. Toxicol.
, vol.9
, pp. 737
-
-
Kenar, J.A.1
Havrilla, C.M.2
Porter, N.A.3
Guyton, J.R.4
Brown, S.A.5
Klemp, K.F.6
Selinger, E.7
-
35
-
-
0019448885
-
-
Baldwin, J. E.; Reed, N. V.; Thomas, E. J. Tetrahedron 1981, 37, 263.
-
(1981)
Tetrahedron
, vol.37
, pp. 263
-
-
Baldwin, J.E.1
Reed, N.V.2
Thomas, E.J.3
-
36
-
-
0033006542
-
-
(a) Upston, J. M.; Terentis, A. C.; Stocker, R. FASEB 1999, 13, 977.
-
(1999)
FASEB
, vol.13
, pp. 977
-
-
Upston, J.M.1
Terentis, A.C.2
Stocker, R.3
-
38
-
-
0035913748
-
-
(c) Culbertson, S. M.; Vinqvist, M. R.; Barclay, L. R. C.; Porter, N. A. J. Am. Chem. Soc. 2001, 123, 8951.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 8951
-
-
Culbertson, S.M.1
Vinqvist, M.R.2
Barclay, L.R.C.3
Porter, N.A.4
-
39
-
-
0037620493
-
-
Pratt, D. A.; Mills, J. H.; Porter, N. A. J. Am. Chem. Soc. 2003, 125, 5801.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 5801
-
-
Pratt, D.A.1
Mills, J.H.2
Porter, N.A.3
-
40
-
-
33845377128
-
-
-1) (a) Burton, G. W.; Doba, T.; Gabe, E. J.; Hughes, L.; Lee, F. L.; Prasad, L.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 7053.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 7053
-
-
Burton, G.W.1
Doba, T.2
Gabe, E.J.3
Hughes, L.4
Lee, F.L.5
Prasad, L.6
Ingold, K.U.7
-
41
-
-
0021066063
-
-
(b) Burton, G. W.; Hughes, L.; Ingold, K. U. J. Am. Chem. Soc. 1983, 105, 5950.
-
(1983)
J. Am. Chem. Soc.
, vol.105
, pp. 5950
-
-
Burton, G.W.1
Hughes, L.2
Ingold, K.U.3
-
42
-
-
0034810395
-
-
-1) (c) Pratt, D. A.; DiLabio, G. A.; Brigati, G.; Pedulli, G. F.; Valgimigli, L. J. Am. Chem. Soc. 2001, 123, 4625.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 4625
-
-
Pratt, D.A.1
DiLabio, G.A.2
Brigati, G.3
Pedulli, G.F.4
Valgimigli, L.5
-
43
-
-
37049094101
-
-
(a) Bascetta, E.; Gunstone, F. D.; Scrimgeour, C. M.; Walton, J. C. J. Chem. Soc., Chem. Commun. 1982, 110.
-
(1982)
J. Chem. Soc., Chem. Commun.
, pp. 110
-
-
Bascetta, E.1
Gunstone, F.D.2
Scrimgeour, C.M.3
Walton, J.C.4
-
44
-
-
37049105194
-
-
(b) Bascetta, E.; Gunstone, F. D.; Walton, J. C. J. Chem. Soc., Perkin Trans. 2 1983, 603.
-
(1983)
J. Chem. Soc., Perkin Trans. 2
, pp. 603
-
-
Bascetta, E.1
Gunstone, F.D.2
Walton, J.C.3
-
45
-
-
3342882241
-
-
note
-
2 trapping at the bis-allylic position (α) decreases in this order.
-
-
-
-
46
-
-
0037772316
-
-
The stability of peroxyl radicals has been shown to be influenced by substituent effects due to hyperconjugation. (a) Pratt, D. A. Porter, N. A. Org. Lett. 2003, 5, 387.
-
(2003)
Org. Lett.
, vol.5
, pp. 387
-
-
Pratt, D.A.1
Porter, N.A.2
-
47
-
-
0034628643
-
-
(b) Kranenburg, M.; Ciriano, M. V.; Cherkasov, A.; Mulder, P. J. Phys. Chem. A 2000, 104, 915.
-
(2000)
J. Phys. Chem. A
, vol.104
, pp. 915
-
-
Kranenburg, M.1
Ciriano, M.V.2
Cherkasov, A.3
Mulder, P.4
-
50
-
-
37049069373
-
-
(c) Beckwith, A. L.; Davies, A. G.; Davison, I. G. E.; Maccoll, A.; Mruzek, M. H. J. Chem. Soc., Chem. Commun. 1988, 475.
-
(1988)
J. Chem. Soc., Chem. Commun.
, pp. 475
-
-
Beckwith, A.L.1
Davies, A.G.2
Davison, I.G.E.3
Maccoll, A.4
Mruzek, M.H.5
-
51
-
-
37049089653
-
-
(d) Avila, D. V.; Davies, A. G.; Davison, I. G. E. J. Chem. Soc., Perkin Trans. 2 1988, 1847.
-
(1988)
J. Chem. Soc., Perkin Trans. 2
, pp. 1847
-
-
Avila, D.V.1
Davies, A.G.2
Davison, I.G.E.3
-
53
-
-
3342936197
-
-
(f) Dang, H.; Davies, A. G.; Davison, I. G. E.; Schiesser, C. H. J. Org. Chem. 1990, 55, 5085.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 5085
-
-
Dang, H.1
Davies, A.G.2
Davison, I.G.E.3
Schiesser, C.H.4
-
54
-
-
0025240854
-
-
(g) Porter, N. A.; Kaplan, J. K.; Dussault, P. H. J. Am. Chem. Soc. 1990, 112, 1266.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 1266
-
-
Porter, N.A.1
Kaplan, J.K.2
Dussault, P.H.3
-
55
-
-
0001300916
-
-
Chan, H. W.; Levett, G.; Matthew, J. A. Chem. Phys. Lipids 1979, 24, 245.
-
(1979)
Chem. Phys. Lipids
, vol.24
, pp. 245
-
-
Chan, H.W.1
Levett, G.2
Matthew, J.A.3
-
57
-
-
0038039810
-
-
(a) Mills, K. A.; Caldwell, S. E.; Dubay, G. R.; Porter, N. A. J. Am. Chem. Soc. 1992, 114, 9689.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 9689
-
-
Mills, K.A.1
Caldwell, S.E.2
Dubay, G.R.3
Porter, N.A.4
-
58
-
-
0000201965
-
-
(b) Porter, N. A.; Mills, K. A.; Carter, R. L. J. Am. Chem. Soc. 1994, 116, 6690.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 6690
-
-
Porter, N.A.1
Mills, K.A.2
Carter, R.L.3
-
59
-
-
0000165255
-
-
(c) Porter, N. A.; Mills, K. A.; Caldwell, S. E.; Dubay, G. R. J. Am. Chem. Soc. 1994, 116, 6697.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 6697
-
-
Porter, N.A.1
Mills, K.A.2
Caldwell, S.E.3
Dubay, G.R.4
-
61
-
-
37049112989
-
-
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.
-
(1984)
J. Chem. Soc., Perkin Trans. 2
, pp. 621
-
-
Brill, W.F.1
-
64
-
-
0001645409
-
-
(d) Boyd, S. L.; Boyd, R. J.; Shi, Z.; Barclay, R. C.; Porter, N. A. J. Am. Chem. Soc. 1993, 115, 687.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 687
-
-
Boyd, S.L.1
Boyd, R.J.2
Shi, Z.3
Barclay, R.C.4
Porter, N.A.5
-
65
-
-
3342979250
-
-
note
-
It has been shown that for allylperoxyl rearrangements, the trans allyl radical-dioxygen reaction is faster than the cis allyl radical-dioxygen reaction (see ref 27c).
-
-
-
-
66
-
-
0141645551
-
-
Wijtmans, M.; Pratt, D. A.; Valgimigli, L.; DiLabio, G. A.; Pedulli, G. F.; Porter, N. A. Angew. Chem., Int. Ed. 2003, 42, 4370.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 4370
-
-
Wijtmans, M.1
Pratt, D.A.2
Valgimigli, L.3
DiLabio, G.A.4
Pedulli, G.F.5
Porter, N.A.6
-
67
-
-
0142228953
-
-
Valgimigli, L.; Brigati, G.; Pedulli, G. F.; DiLabio, G. A.; Mastragostino, M.; Arbizzani, C.; Pratt, D. A. Chem.-Eur. J. 2003, 9, 4997.
-
(2003)
Chem.-Eur. J.
, vol.9
, pp. 4997
-
-
Valgimigli, L.1
Brigati, G.2
Pedulli, G.F.3
DiLabio, G.A.4
Mastragostino, M.5
Arbizzani, C.6
Pratt, D.A.7
|