Novel tocopheryl compounds XXIV. Studies into the nitrosation chemistry of γ-tocopherol: preparation of 5-nitroso-γ-tocopherol via an organomercury derivative of vitamin E

Tetrahedron

Volumn 63, Issue 19, 2007, Pages 4067-4073

  Patel, Anjan ^a   Liebner, Falk ^a   Mereiter, Kurt ^b   Netscher, Thomas ^c   Rosenau, Thomas ^a  

^a UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

^b VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^c Research and Development   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

5 NITROSO GAMMA TOCOPHEROL; 5,6 TOCOPHERYLDIONE; 5,6 TOCOPHERYLDIONE 5 OXIME; ALPHA TOCOPHEROL; GAMMA TOCOPHEROL; HYDROXYLAMINE; ORGANOMERCURY COMPOUND; OXYGEN; QUINONE DERIVATIVE; TOCOPHEROL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DENSITY FUNCTIONAL THEORY; DRUG SYNTHESIS; EQUILIBRIUM CONSTANT; HIGH TEMPERATURE; NITROSATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL;

EID: 34047253034     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.120     Document Type: Article

References (39)

1. Baldenius K.U., von dem Bussche-Hünnefeld L., Hilgemann E., Hoppe P., and Stürmer R. Ullmann's Encyclopedia of Industrial Chemistry Vol. A27 (1996), VCH, Weinheim 478-488, 594-597
2. Netscher T. Chimia 50 (1996) 563-567
3. Machlin L.J. Vitamin E: a Comprehensive Treatise (1980), Marcel Dekker, New York, NY
4. Kamal-Eldin A., and Appelqvist L.A. Lipids 31 (1996) 671-701
5. Hoglen N.C., Waller S.C., Sipes I.G., and Liebler D.C. Chem. Res. Toxicol. 10 (1997) 401-407
6. Marcinkiewicz S. Acta Pol. Pharm. 24 (1967) 375-378
7. Yenes S., and Messeguer A. Tetrahedron 55 (1999) 14111-14122
8. Cooney R.V., Franke A.A., Harwood P.J., Pigott V.H., Custer L.J., and Mordan L.J. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 1771-1775
9. Cooney R.V., Harwood P.J., Franke A.A., Narala K., Sundström A.K., Berggren P.O., and Mordan L.J. Free Radic. Biol. Med. 19 (1995) 259-269
10. Christen S., Woodall A.A., Shigenaga M.K., Southwell-Keely P.T., Duncan M.W., and Ames B.N. Proc. Natl. Acad. Sci. U.S.A. 94 (1997) 3217-3222
11. Singh R.J., Goss S.P.A., Joseph J., and Kalyanaraman B. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 12912-12917
12. Williams D.L.H. Nitrosation Reactions and the Chemistry of Nitric Oxide (2004), Elsevier, Amsterdam
13. Raczyńska E.D., Krygowski T.M., Zachara J.E., Ośmialowski B., and Gawinecki R. J. Phys. Org. Chem. 18 (2005) 892-897
14. Enchev V., Ivanova G., and Stoyanov N. J. Mol. Struct. (Theochem) 640 (2003) 149-162
15. Krzan A., Crist D.R., and Horák V. J. Mol. Struct. (Theochem) 528 (2000) 237-244
16. Analytical data and procedures not given here as they are not pertinent to the matter discussed.
17. 13C NMR Data for Organometallic Compounds (1981), Academic, London
18. 13C NMR Spektroskopie (1984), Georg Thieme, Stuttgart, New York, NY
19. Beyer A. Ber. Dtsch. Chem. Ges. 7 (1874) 1638
20. Smith L.J., and Taylor F.L. J. Am. Chem. Soc. 57 (1935) 2460
21. Grdenic D., Vrdoljak V., and Korpar-Colig B. Croat. Chem. Acta 69 (1996) 1361-1366
22. Here it is interesting to note that oximes are usually quite stable compounds that form readily from keto compound and hydroxylamine. The stability of quinone monoximes is significantly lower, and the presence of an ortho-hydroxy substituent has an additional destabilizing effect.
23. In both cases the intramolecularly hydrogen-bonded six-membered ring form of the syn-oximes was considered.
24. Rosenau T., Ebner G., Stanger A., Perl S., and Nuri L. Chem.-Eur. J. 11 (2005) 280-287
25. Rosenau T., and Stanger A. Tetrahedron Lett. 46 (2005) 7845-7848
26. IUPAC-IUB. Eur. J. Biochem. 123 (1982) 473-475
27. IUPAC-IUB Commission on Biochemical Nomenclature (CBN). Arch. Biochim. Biophys. 165 (1974) 1-8
28. Urano S., Hattori Y., Yamanoi S., and Matsuo M. Chem. Pharm. Bull. 28 (1980) 1992-1998
29. Brownstein S., and Ingold K.U. J. Org. Chem. 54 (1989) 560-569
30. Lee C., Yang W., and Parr R.G. Phys. Rev. B37 (1988) 785-789
31. Miehlich B., Savin A., Stoll H., and Preuss H. Chem. Phys. Lett. 157 (1989) 200-206
32. Becke A.D. Phys. Rev. A38 (1988) 3098-3100
33. Becke A.D. J. Chem. Phys. 98 (1993) 5648-5652
34. Hariharan P.C., and Pople J.A. Theor. Chim. Acta 28 (1973) 213-222
35. Francl M.M., Pietro W.J., Hehre W.J., Binkley J.S., Gordon M.S., DeFrees D.J., and Pople J.A. J. Chem. Phys. 77 (1982) 3654-3665
36. Fisher G.S. Ind. Eng. Chem., Anal. Ed. 17 (1945) 224-227
37. Marcinkiewicz S., Green J., and McHale D. J. Chem. Soc., Perkin Trans. 1 (1966) 1431-1433
38. Smith L.I., Irwin W.B., and Ungnade H. J. Am. Chem. Soc. 61 (1939) 2424-2429
39. Frampton V.L., Skinner W.A., Cambour P., and Bailey P.S. J. Am. Chem. Soc. 82 (1960) 4632-4634