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Volumn 72, Issue 9, 2007, Pages 3268-3281

Vitamin E chemistry. studies into initial oxidation intermediates of α-tocopherol: Disproving the involvement of 5a-C-centered "chromanol methide" radicals

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL CHEMISTRY; SUPRAMOLECULAR STRUCTURES; TOCOPHEROL; VITAMIN E;

EID: 34247614885     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062553j     Document Type: Article
Times cited : (32)

References (75)
  • 1
    • 0020122108 scopus 로고
    • IUPAC-IUB, Nomenclature of Tocopherols and Related Compounds
    • IUPAC-IUB Eur. J. Biochem. 1982, 123, 473-475. Nomenclature of Tocopherols and Related Compounds.
    • (1982) Eur. J. Biochem , vol.123 , pp. 473-475
  • 2
    • 0006007876 scopus 로고
    • IUPAC-IUB Commission on Biochemical Nomenclature CBN
    • IUPAC-IUB Commission on Biochemical Nomenclature (CBN) Arch. Biochim. Biophys. 1974, 165, 1-8.
    • (1974) Arch. Biochim. Biophys , vol.165 , pp. 1-8
  • 3
    • 34247568031 scopus 로고    scopus 로고
    • Baldenius, K. U.; Von dem Bussche-Hünnefeld, L.; Hilgemann, E.; Hoppe, P.; Stürmer, R. In Ullmann's Encyclopedia of Industrial Chemistry; VCH Verlagsgesellschaft: Weinheim, 1996; A27, pp 478-488, 594-597.
    • Baldenius, K. U.; Von dem Bussche-Hünnefeld, L.; Hilgemann, E.; Hoppe, P.; Stürmer, R. In Ullmann's Encyclopedia of Industrial Chemistry; VCH Verlagsgesellschaft: Weinheim, 1996; Vol. A27, pp 478-488, 594-597.
  • 4
    • 0001069947 scopus 로고    scopus 로고
    • Netscher, T. Chimia 1996, 50, 563-567.
    • (1996) Chimia , vol.50 , pp. 563-567
    • Netscher, T.1
  • 6
    • 0000145287 scopus 로고
    • See also a later review
    • (b) See also a later review: Badger, G. M. Quart. Rev. Chem. Soc. 1951, 5, 147.
    • (1951) Quart. Rev. Chem. Soc , vol.5 , pp. 147
    • Badger, G.M.1
  • 44
    • 33746375063 scopus 로고    scopus 로고
    • In the case of a stepwise process loss of one electron and one proton, an phenoxonium cation intermediate might well be involved, which has recently been shown to be quite stable: Lee, S. B, Willis, A. C, Webster, R. D. J. Am. Chem. Soc. 2006, 128, 9332-9333
    • In the case of a stepwise process (loss of one electron and one proton), an phenoxonium cation intermediate might well be involved, which has recently been shown to be quite stable: Lee, S. B.; Willis, A. C.; Webster, R. D. J. Am. Chem. Soc. 2006, 128, 9332-9333.
  • 45
    • 34247628592 scopus 로고    scopus 로고
    • Also the conversion of p-quinoid into o-quinoid structures in the chemistry of α-tocopherol involves such an intermediate, e.g., the reaction of p-tocopheryl quinone with acetyl halide or trimethylsilyl halide to O-protected 5a-halotocopherols: (a) Dallacker, F.; Eisbach, R.; Holschbach, M. Chem. Ztg. 1991, 115, 113-116.
    • Also the conversion of p-quinoid into o-quinoid structures in the chemistry of α-tocopherol involves such an intermediate, e.g., the reaction of p-tocopheryl quinone with acetyl halide or trimethylsilyl halide to O-protected 5a-halotocopherols: (a) Dallacker, F.; Eisbach, R.; Holschbach, M. Chem. Ztg. 1991, 115, 113-116.
  • 47
    • 0037204689 scopus 로고    scopus 로고
    • This trapping reaction has been frequently applied in vitamin E chemistry, its kinetics and products being well-known; cf. for instance: (a) Rosenau, T, Potthast, A, Elder, T, Lange, T, Sixta, H, Kosma, P. J. Org. Chem. 2002, 67, 3607-3614
    • This trapping reaction has been frequently applied in vitamin E chemistry, its kinetics and products being well-known; cf. for instance: (a) Rosenau, T.; Potthast, A.; Elder, T.; Lange, T.; Sixta, H.; Kosma, P. J. Org. Chem. 2002, 67, 3607-3614.
  • 49
    • 34247578265 scopus 로고    scopus 로고
    • References 6 and 41
    • (c) References 6 and 41.
  • 55
  • 57
    • 0005820691 scopus 로고
    • For the 8a-methoxy-tocopherone. see
    • For the 8a-methoxy-tocopherone. see: Omura, K. J. Org. Chem. 1989, 54, 1987-1990.
    • (1989) J. Org. Chem , vol.54 , pp. 1987-1990
    • Omura, K.1
  • 58
    • 0025150365 scopus 로고
    • For other 8a-alkoxy-tocopherones, see: a
    • For other 8a-alkoxy-tocopherones, see: (a) Liebler, D. C.; Baker, P. F.; Kaysen, K. L. J. Am. Chem. Soc. 1990, 112, 6995-7000.
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 6995-7000
    • Liebler, D.C.1    Baker, P.F.2    Kaysen, K.L.3
  • 64
    • 34247629717 scopus 로고    scopus 로고
    • Preedy, V, Watson R, Eds, CABI Publishing: Oxford, Chapters 3 and 6
    • Rosenau, T. In Encyclopedia of Vitamin E; Preedy, V., Watson R., Eds.; CABI Publishing: Oxford, 2006; Chapters 3 and 6.
    • (2006) Encyclopedia of Vitamin E
    • Rosenau, T.1
  • 65
    • 34247572055 scopus 로고    scopus 로고
    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Zakrzewski, V. G, Montgomery, J. A, Stratman, R. E, Burant, J. C, Dapprich, S, Millam, J. M, Barone, V, Cossi, M, Cammi, R, Mennucci, B, Pomelli, C, Adamo, C, Clifford, S, Ochterski, J, Petersson, G. A, Ayala, P. Y, Cui, Q, Morokuma, K, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Cioslowski, J, Ortiz, J. V, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Gomperts, R, Martin, R. L, Fox, D. J, Keith, T, Al-Laham, M. A, Peng, C. Y, Nananyakkara, A, Gonzalez, C, Challacombe, M, Gill, P. M. W, Johnson, B, Chen, W, Wong, M. W, Andres, J. L, Head-Gordon, M, Replogle, E. S, Pople, J. A. Gaussian 98, revision A.6; Gaussian Inc, Pittsburgh, 1998
    • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratman, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nananyakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.6; Gaussian Inc.: Pittsburgh, 1998.
  • 66
    • 34247566709 scopus 로고    scopus 로고
    • Spartan Pro; Wavefunction, Inc.: Irvine, CA, 2004.
    • Spartan Pro; Wavefunction, Inc.: Irvine, CA, 2004.
  • 69
    • 4243553426 scopus 로고
    • Becke, A. D. Phys. Rev. 1988, A38, 3098-3100.
    • (1988) Phys. Rev , vol.A38 , pp. 3098-3100
    • Becke, A.D.1
  • 73
    • 34247561398 scopus 로고    scopus 로고
    • Prepared according to literature, giving literature-consistent NMR data: Yenes, S.; Messeguer, A. Tetrahedron 1999, 55, 1411-1422.
    • Prepared according to literature, giving literature-consistent NMR data: Yenes, S.; Messeguer, A. Tetrahedron 1999, 55, 1411-1422.


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