Oxidations of benzyl and phenethyl phenyl sulfides. Implications for the mechanism of the microsomal and biomimetic oxidation of sulfides

Tetrahedron

Volumn 53, Issue 36, 1997, Pages 12287-12298

  Baciocchi, Enrico ^a   Lanzalunga, Osvaldo ^a   Pirozzi, Bruno ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

SULFOXIDE;

ARTICLE; DRUG SYNTHESIS; ELECTRON TRANSPORT; IN VITRO STUDY; MODEL; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; TEMPERATURE;

EID: 0030828444     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00560-7     Document Type: Article

References (44)

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13. Dunford, H. B., Stilman, J. S. Coord. Chem. Rev. 1976, 19, 187; Ortiz de Montellano, P. R. Ann. Rev Pharmacol. Toxicol. 1992, 32, 89; Kobayashi, S.; Nakano, M.; Goto, T.; Kimura, T.; Schaap, A. P. Biochem. Biophys. Res. Commun. 1986, 135, 166; Kobayashi, S.; Nakano, M.; Kimura, T.; Schaap, A. P. Biochemistry 1987, 26, 5019-5022; Doerge, D. R. Arch Biochem. Biophys. 1986, 244, 678; Doerge, D. R.; Cooray, N. M.; Brewster, M. E. Biochemistry 1991, 30, 8960; Harris, R. Z.; Newmyer, S. L.; Ortiz de Montellano, P. R. J. Biol. Chem. 1993, 268, 1637; Ozaki, S.-I.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1994, 116, 4487; Ozaki, S.-L; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1995, 117, 7056; Perez, U.; Dunford, H. B. Biochim. Biophys. Acta 1990, 1038, 98; Colonna, S.; Gaggero, N.; Carrea, G.; Pasta, P. J. Chem. Soc Chem. Commun. 1992, 357.
14. Dunford, H. B., Stilman, J. S. Coord. Chem. Rev. 1976, 19, 187; Ortiz de Montellano, P. R. Ann. Rev Pharmacol. Toxicol. 1992, 32, 89; Kobayashi, S.; Nakano, M.; Goto, T.; Kimura, T.; Schaap, A. P. Biochem. Biophys. Res. Commun. 1986, 135, 166; Kobayashi, S.; Nakano, M.; Kimura, T.; Schaap, A. P. Biochemistry 1987, 26, 5019-5022; Doerge, D. R. Arch Biochem. Biophys. 1986, 244, 678; Doerge, D. R.; Cooray, N. M.; Brewster, M. E. Biochemistry 1991, 30, 8960; Harris, R. Z.; Newmyer, S. L.; Ortiz de Montellano, P. R. J. Biol. Chem. 1993, 268, 1637; Ozaki, S.-I.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1994, 116, 4487; Ozaki, S.-L; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1995, 117, 7056; Perez, U.; Dunford, H. B. Biochim. Biophys. Acta 1990, 1038, 98; Colonna, S.; Gaggero, N.; Carrea, G.; Pasta, P. J. Chem. Soc Chem. Commun. 1992, 357.
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17. Dunford, H. B., Stilman, J. S. Coord. Chem. Rev. 1976, 19, 187; Ortiz de Montellano, P. R. Ann. Rev Pharmacol. Toxicol. 1992, 32, 89; Kobayashi, S.; Nakano, M.; Goto, T.; Kimura, T.; Schaap, A. P. Biochem. Biophys. Res. Commun. 1986, 135, 166; Kobayashi, S.; Nakano, M.; Kimura, T.; Schaap, A. P. Biochemistry 1987, 26, 5019-5022; Doerge, D. R. Arch Biochem. Biophys. 1986, 244, 678; Doerge, D. R.; Cooray, N. M.; Brewster, M. E. Biochemistry 1991, 30, 8960; Harris, R. Z.; Newmyer, S. L.; Ortiz de Montellano, P. R. J. Biol. Chem. 1993, 268, 1637; Ozaki, S.-I.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1994, 116, 4487; Ozaki, S.-L; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1995, 117, 7056; Perez, U.; Dunford, H. B. Biochim. Biophys. Acta 1990, 1038, 98; Colonna, S.; Gaggero, N.; Carrea, G.; Pasta, P. J. Chem. Soc Chem. Commun. 1992, 357.
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27. To be published.
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31. A fast equilibrium between 6a and 6b is suggested by the observation that the total yield of products from 6b relative to that from 6a increases in the presence of AcOK (Table 1). The base shifts the equilibrium towards 6b by probably favouring the deprotonation from the α to sulfur C-H bond more than the deprotonation from the benzylic C-H bond of 6a.
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