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Xenobiotica
the fate of foreign compounds in biological systems
Volume 25, 1995 - Issue 7
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Original Article

Fragmentation reactions of aromatic cation radicals: a tool for the detection of electron transfer mechanisms in biomimetic and enzymatic oxidations

Pages 653-666 | Received 12 Nov 1994, Published online: 27 Aug 2009

References

  • Amodeo R., Baciocchi E., Crescenzi M., Lanzalunga O. Selectivity and mechanism in the microsomal benzylic hydroxylation. Tetrahedron Letters 1990; 31: 3477–3480
  • Baciocchi E. Side-chain reactivity of aromatic radical cations. Acta Chemica Scandinavica 1990; 44: 645–652
  • Baciocchi E., Crescenzi M. Selectivity and mechanism in the side-chain halogenation of methylbenzenes promoted photochemically and by metal complexes in the presence of halide ions. Tetrahedron 1988; 44: 6525–6536
  • Baciocchi E., Crescenzi M. Solvent and structure effect in the photobromination of benzyltrimethylsilanes. A mechanistic changeover from hydrogen-atom transfer to electron-transfer. Angewandte Chemie International Edition in English 1990a; 29: 658–659
  • Baciocchi E., Crescenzi M., Fasella E., Mattioli M. A kinetic study of the electron transfer initiated carbon-silicon bond cleavage reactions of benzyltrialkylsilanes promoted by 12-tungstocobalt(III)ate ion. Journal of Organic Chemistry 1992; 57: 4684–4689
  • Baciocchi E., Crescenzi M., Lanzalunga O. Electron transfer vs. hydrogen atom transfer in iron(III) porphyrins catalysed benzylic oxidations. Journal of the Chemical Society, Chemical Communications 1990b; 687–688
  • Baciocchi E., Dalla Cort D., Eberson L., Mandolini L., Rol C. Substituent effects on the intramolecular selectivity and free energy relationships in aromatic and metal ion oxidation of 5-X-1,2,3-trimethylbenzenes. Journal of Organic Chemistry 1986; 51: 4544–4548
  • Baciocchi E., Del Giacco T., Murgia S. M., Sebastiani G. V. Rate and mechanism for the reaction of nitrate radical with aromatic and alkylaromatic compounds in acetonitrile. Journal of the Chemical Society, Chemical Communications 1987; 1246–1248
  • Baciocchi E., Del Giacco T., Rol C., Sebastiani G. V. The role of nitrate radical in the photochemical side-chain nitrooxylation of alkylbenzenes by cerium(IV) ammonium nitrate in acetonitrile. Tetrahedron Letters 1985; 26: 541–544
  • Baciocchi E., Del Giacco T., Rol C., Sebastiani G. V. Carbon- -silicon bond cleavage in the oxidation of benzylic silanes by cerium(IV) ammonium nitrate. Tetrahedron Letters 1989; 30: 3573–3576
  • Baciocchi E., Lanzalunga O. Side-chain oxidation of benzyltrimethylsilanes by iodosylbenzene in the presence of iron and manganese porphyrins. Tetrahedron 1993; 49: 7267–7276
  • Baciocchi E., Lanzalunga O., Marconi F. The mechanism of the enzymatic and biomimetic oxidation of aromatic sulphides and sulphoxides. Tetrahedra Letters 1994; 35: 9771–9774
  • Baciocchi E., Rol C., Sebastiani G. V., Serena B. Photochemical nitrooxylation of methylbenzenes by cerium(IV) ammonium nitrate in acetonitrile. Tetrahedron Letters 1984a; 1945–1946
  • Baciocchi E., Ruzziconi R. The reactions of cerium(IV) ammonium nitrate and cobalt(III) acetate with 1,2-diphenylethanes in acetic acid. Evidence against the involvement of radical cations in the side-chain oxidations of alkylbenzenes by Co(OAc)3. Journal of the Chemical Society, Chemical Communications 1984; 445–446
  • Borg R. M., Heuckeroth R. O., Lan A. J. V., Quillen S. L., Mariano P. S. Arene-iminium salt electron-transfer photochemistry. Mechanistically interesting photoaddition processes. Journal of the American Chemical Society 1987; 109: 2728–2737
  • Bowry V. W., Ingold K. U. A radical-clock investigation of microsomal cytochrome P450 hydroxylation of hydrocarbons. Rate of oxygen rebound. Journal of the American Chemical Society 1991; 113: 5699–5707
  • Del Giacco T., Baciocchi E., Steenken S. One electron oxidation of alkybenzenes by photochemically produced NO3. Evidence for an inner sphere mechanism. Journal of Physical Chemistry 1993; 67: 5451–5456
  • Dessau R. M., Shih S., Heiba E. I. Oxidation by metal salts. VI. A new chemical method for the generation of aromatic radical cations. Journal of the American Chemical Society 1970; 92: 412–413
  • Dinnocenzo J. P., Farid S., Goodman J. L., Gould I. R., Todd W. P. Photooxidative cleavage of organosilanes. Molecular Crystals Liquid Crystals 1991; 194: 151–157
  • Dinnocenzo J. P., Farid S., Goodman J. L., Gould I. R., Todd W. P., Mattes S. L. Nucleophile-assisted cleavage of silicon cation radicals. Journal of the American Chemical Society 1989; 111: 8973–8975
  • Dixon W. T., Murphy D. The electron spin resonance spectra of alkyl aryl ether radical cations. Journal of the Chemical Society, Perkin Transactions II 1976; 1823–1828
  • Eberson L. Electron transfer reactions in organic chemistry. Advances in Physical Organic Chemistry 1982; 18: 79–185
  • Eberson L. Electron transfer reactions in organic chemistry. 4. A mechanistic study of the oxidation of p-methoxytoluene by 12-tungstocobalt(III)ate ion. Journal of the American Chemical Society 1983; 105: 3192–3199
  • Eberson L. Electron Transfer Reactions in Organic Chemistry. Springer, Berlin 1987
  • Eberson L. Outer-sphere electron transfer reactions, rare events in organic chemistry. New Journal of Chemistry 1992; 16: 151–156
  • Eriksen J., Foote C. S., Parker T. L. Photosensitized oxygenation of alkenes and sulphides via a non-singlet-oxygen mechanism. Journal of the American Chemical Society 1977; 99: 6455–6456
  • Guengerich F. P., Macdonald T. L. Chemical mechanisms of catalysis of cytochrome P450: a unified view. Accounts of Chemical Research 1984; 17: 9–16
  • Guengerich F. P., Macdonald T. L. Sequential electron transfer reactions catalysed by cytochrome P450 enzymes. Advances in Electron Transfer Chemistry, P. S. Mariano. JAI, London 1993; vol. 3: 191–241
  • Meunier B. Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage. Chemicals Reviews 1992; 42: 1411–1456
  • Mizuno K., Ikeda M., Otsuji Y. A novel photosubstitution of dicyanobenzenes by allylic and benzylic silanes. Tetrahedron Letters 1985; 26: 461–464
  • Oae S., Watanabe Y., Fujimori K. Biomimetic oxidation of organic sulphides with TPPFe(III)/imidazole/hydrogen peroxide. Tetrahedron Letters 1982; 23: 1189–1192
  • Ortiz de Montellano. Cytochrome P450. Plenum, New York 1986
  • Oxygen activation and transfer. Cytochrome P450, P. R. Ortiz de Montellano. Plenum, New York 1986a; 217–271
  • Takata T., Tajima R., Ando W. Selective oxidation of sulphides by ArIO-metalloporphyrin system. An enzymatic model S-oxidation. Phosphorous and Sulphur 1983; 16: 67–78
  • Watanabe Y., Numata T., Iyanagi T., Oae S. Enzymatic oxidation of alkyl sulphides by cytochrome P450 and hydroxyl radical. Bulletin of the Chemical Society of Japan 1981; 54: 1163–1170
  • Watanabe Y., Iyanagi T., Oae S. One electron transfer mechanism in the enzymatic oxidation of sulphoxide to sulphone promoted by a reconstituted system with purified cytochrome P450. Tetrahedron Letters 1982; 23: 533–536
  • Yoshida J., Murata T., Isoe S. Electrochemical oxidation of organosilicon compounds. I. Oxidative cleavage of carbon-silicon bond in alylsilanes and benzylsilanes. Tetrahedron Letters 1986; 27: 3373–3376

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