15
Views
12
CrossRef citations to date
0
Altmetric
Original Article

Redox Behaviour of Phenolic Porphyrins in Basic Solutions: A Reappraisal

, &
Pages 19-29 | Received 18 Feb 1995, Published online: 07 Jul 2009

References

  • This paper is part 20 in a series entitled “Facile Aerial Oxidation of Porphyrins”. Part 19 is L.R. Milgrom, J.P. Hill, and P.J.F. Dempsey (1994) Alkylation of 5,10,15-tris(3,5-di-t-butyl-4-hydroxyphenyl)-20–(4-pyridyl) por-phyrin. Tetrahedron, 50: 13477–13484
  • Milgrom L. R., Hill J. P., Flitter W. D. See Facile Aerial Oxidation of Porphyrins. Part 16. Phenolic porphyrins without t-butyl substituents. Journal of the Chemical Society, Perkin Transactions 2 1994; 521–524
  • Milgrom L. R. The facile aerial oxidation of a porphyrin. Tetrahedron 1983; 39: 3895–3898
  • Milgrom L. R., Flitter W. D. Improved generation of porphyrin radicals via conproportionation. Journal of the Chemical. Society, Chemical Communications 1991; 1492–1494
  • Milgrom L. R., Hill J. P., Flitter W. D. Formation of hydroxyl radicals during the facile aerial oxidation of a phenolic porphyrin. Journal of the Chemical Society, Chemical Communications 1992; 773–775
  • Albery W. J., Bartlett P. N., Jones C. C., Milgrom L. R. Facile aerial oxidation of a porphyrin. Part 2. Meso tetrakis(3,4,5-trihydroxyphenyl)porphyrin. Journal of Chemical Research 1985; (S)362–365: (M)3801–3814
  • Milgrom L. R., Yahioglu G., Flitter W. D. Aerial oxidation of a redox-active porphyrin in the presence of a spin-trap. Redox Report 1994; 1: 145–150
  • See J.A. Weil, Anderson J. K. The determination and reaction of 2,2-diphenyl-l-picrylhydrazyl with thiosalicylic acid. Journal of the Chemical Society 1965; 5567–5570
  • Williams D. E. Crystallographic data for 2,2-diphenyl-1-picrylhydrazyl. Journal of the Chemical Society 1965; 7535–7536
  • a, L.R. Milgrom, C.C. Jones and A. Harriman (1988) Facile aerial oxidation of a porphyrin. Part 3. Some metal complexes of meso-tetrakis(3,5di-t-butyl-4-hydroxyphenyl) porphyrin. Journal of the. Chemical Society, Perkin Transactions 2. 71–79: b, A. J. Golder, L.R. Milgrom, K.B. Nolan, and D.C. Povey (1989) 5,10,15,20Mesotetrakis(3,5-di-t-butyl-4-quinomethide)porphyrinogen: a highly puckered tetrapyrrolic macrocycle from the facile aerial oxidation of a phenolic porphyrin. Journal of the Chemical Society, Chemical Communications, 1751–1753 c, H. Scheer and H.H. Inhoffen (1978) Hydroporphyrins: reactivity, spectroscopy, and hydroporphyrin analogues in The Porphyrins (ed. D. Dolphin), Academic Press, London and New York, pp. 45–90.
  • Milgrom L. R., Mofidi N., Jones C. C., Harriman A. Facile aerial oxidation of a porphyrin. Part 4. Un-symmetrical meso-tetraarylporphyrins with 3,5-di-t-butyl-4-hydroxyphenyl and 4-hydroxyphenyl substituents. Journal of the Chemical Society Perkin Transactions 2 1989; 301–309
  • That porphyrins 1, 4, and 5 give esr spectra in deoxyge-nated as well as undegassed basic solutions, contradicts earlier reports (see references 2 and 7). An intermittant, non-reproducable, fault (now rectified) in the field-set potentiometer of the Varian instrument was found to be the apparent source of this contradiction.
  • a, J.L. Roberts, Jr., H. Sugimoto, W.C. Barette, Jr., and D.T. Sawyer (1985) One-electron reduction of anthraquinone by hydroxide ion in aprotic media. Journal of the American Chemical Society, 107, 4556–4557: b, D.T. Sawyer (1991) Oxygen Chemistry, Oxford University Press, New York and Oxford, p. 201.
  • Roberts J. L., Oxford, Jr., Morrison M. M., Sawyer D. T. Base-induced generation of superoxide ion and hydroxyl radical from hydrogen peroxide. Journal of the American Chemical Society 1978; 100: 329–330
  • Milgrom L. R., Flitter W. D. Facile aerial oxidation of a porphyrin. Part 12. Spin-trapping of solvent-derived intermediates from the addition of base to an oxidised porphyrin. Tetrahedron 1992; 48: 2951–2956
  • Scheer H. Synthesis and stereochemistry of hydroporphyrins in. The Porphyrins, D. Dolphin. Academic Press, London and New York 1978; 1–44
  • Moore H. W., Wikholm R. J. Rearrangements of quinones in. The Chemistry of Quinonoid Compounds, S. Patai. John Wiley & Sons, London 1974; 441–446
  • The zinc complex of porphyrin 1 has been shown to catalyse the two-electron reduction of dioxygen: T.A. Evans, G.S. Srivatsa, D.T. Sawyer and T.G. Traylor (1985) Redox chemistry of tetrakis(3,5-di-tert-butyl-4-hydroxyphenyl) porphine an its zinc(II) complex in dimethylformamide. Inorganic Chemistry, 24: 4733–4735
  • Eschenmoser A. Vitamin B12: experiments conceming the origin of its molecular structure. Angewandte Chemie, International Edition, (English) 1988; 27: 5–39

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.