Dioxygen activation by Bi(III) compounds: Air oxidation of thiols to their disulfides

Main Group Chemistry

Volumn 12, Issue 2, 2013, Pages 125-138

  Ioannou, Panayiotis V ^a  

^a UNIVERSITY OF PATRAS   (Greece)

Author keywords

Bis(dimethylarsinato)(nitrato)bismuth monohydrate; Bismuth nitrate pentahydrate; Dioxygen activation; Disulfides; Thiols

Indexed keywords

EID: 85013587536     PISSN: 10241221     EISSN: 17451167     Source Type: Journal    
DOI: 10.3233/MGC-130095     Document Type: Article

References (42)

1. G. Bellomo, M. Vairetti, L. Stivala, F. Mirabelli, P. Richelmi and S. Orrenius, Demonstration of nuclear compartmentalization of glutathione in hepatocytes, Proc Natl Acad Sci USA 89 (1992), 4412-4416.
2. G.G. Briand and N. Burford, Bismuth compounds and preparations with biological or medicinal relevance, Chem Rev 99 (1999), 2601-2657.
3. G.M. Brown, The crystal and molecular structure of 6-mercaptopurine monohydrate. A second, independet X-ray diffraction investigation, Acta Cryst B25 (1969), 1338-1353.
4. W.W. Cleland, Dithiothreitol, a new protective reagent for SH groups, Biochemistry 3 (1964), 480-482.
5. R.M.C. Dawson, D.C. Elliott, W.H. Elliott and K.M. Jones, Data for Biochemical Research, 2nd ed., Oxford University Press, London, 1969.
6. I.L. Doerr, I. Wempen, D.A. Clarke and J.J. Fox, Thiation of nucleosides. III. Oxidation of 6-mercaptopurines, J Org Chem 26 (1961), 3401-3409.
7. L.J. Farrugia, F.J. Lawlor and N.C. Norman, Bismuth(III) thiolates: Syntheses and the structures of a neutral thiolate and a thiolato anion, Polyhedron 14 (1995), 311-314.
8. Gmelins Handbuch der Anorganishen Chemie, Sauerstoff, Verlag Chemie, Weinheim, 1958, Lieferung 3, pp. 384-385.
9. I.B. Golovanov and S.M. Zhenodarova, Quantitative structure-property relationship. XXIII. Solubility of oxygen in organic solvents, Russian J Gen Chem 75 (2005), 1795-1797.
10. 3As: Evidence for binding and activation of triplet dioxygen by As(III), Phosphorus, Sulfur, and Silicon 181 (2006), 363-376.
11. M.M. Hashemi and Z. Karimi-Jaberi, Oxidation of thiols to disulfides by oxygen in the presence of cobalt(II) and manganese(II) salts of 4-aminobenzoic acid supported on silica gel, Monatsh Chem 135 (2004), 41-43 and references therein.
12. J. Hine, Physical Organic Chemistry, 2nd ed., McGraw-Hill, NewYork, (1962), pp. 81-103.
13. R. Hua, Recent advances in bismuth-catalyzed organic synthesis, Current Organic Synthesis 5 (2008), 1-27.
14. 2O, with some heterobifunctional aliphatic thiols, Main Group Chem 10 (2011), 243-254.
15. 2O, for the preparation of tris(arylthio)bismuthines, Main Group Chem 10 (2011), 255-264.
16. P.V. Ioannou, Dimethylphosphinato and dimethylarsinato complexes of Sb(III) and Bi(III) and their chemistry, Monatsh Chem 143 (2012), 1349-1356.
17. P.V. Ioannou and G.M. Tsivgoulis, Preparation of thiolates of arsenic(III) and bismuth(III) with dithioerythritol, 2- mercaptoethanesulfonic acid and its sodium salt, 6-mercaptopurine and its riboside, Main Group Chem 11 (2012), 89-102.
18. 2, Z Anorg Allg Chem 633 (2007), 2077-2084.
19. N. Iranpoor and B. Zeynizadeh, Air oxidative coupling of thiols to disulfides catalyzed by Fe(III)/NaI, Synthesis (1999), 49-50.
20. A.R. Katritzky and R.A. Jones, Infrared absorption of heteroaromatic and benzenoid six-membered monocyclic nuclei. Part X. Pyridones and pyridthiones, J Chem Soc (1960), 2947-2953.
21. 2) in aqueous media, J Am Chem Soc 103 (1981), 2203-2206.
22. 2O: An inexpensive and mild reagent for the efficient and clean oxidation of thiols to disulfides, Bull Korean Chem Soc 24 (2003), 885-886 and references therein.
23. H. Klostermeyer and R.E. Humbel, The chemistry and biochemistry of insulin, Angew Chem Int Edit 5 (1966), 807-822.
24. 2O, Acta Cryst C41 (1985), 1144-1145.
25. 15N CIDNP investigations of peroxynitric acid nitration of L-tyrosine and related compounds, Org Biomol Chem 4 (2006), 721-729.
26. A.L. Lehninger, Biochemistry, Worth, New York, (1970), p. 704.
27. S.G. Mautner, S.-H. Chu and C.M. Lee, Studies on 2-selenopyridine and related compounds, J Org Chem 27 (1962), 3671-3673.
28. A.K. Misra and G. Agnihotri, Nitric acid mediated oxidative transformation of thiols to disulfides, Synth Commun 34 (2004), 1079-1085 and references therein.
29. W.I. Patterson and V. du Vigneaud, The synthesis of homocysteine, J Biol Chem 111 (1935), 393-398.
30. 1H NMR Spectra, Edition I, Volume I, Aldrich Chemical Company, USA (1993).
31. D.L. Rabenstein and Y. Thieriault, A nuclear magnetic resonance study of the kinetics and equilibria for the oxidation of penicillamine and N-acetyl penicillamine by glutathione disulfide, Can J Chem 62 (1984), 1672-1680.
32. T.V. Rao, K.N. Rao, S.L. Jain and B. Sain, Cobalt phthalocyanine mediated aerobic oxidation of thiols: A simple and convenient preparation of disulfides, Synth Commun 32 (2002), 1151-1157.
33. J. Ricci and I. Bernal, The crystal structure of _-bis(p-nitrophenyl) disulfide, J Am Chem Soc 91 (1969), 4078-4082.
34. P.J. Sadler, H. Sun and H. Li, Bismuth(III) complexes of the tripeptide glutathione (γ-L-Glu-L-Cys-Gly), Chem Eur J 2 (1996), 701-708.
35. N. Scott, K.M. Hatlelid, N.E.MacKenzie and D.E. Carter, Reactions of arsenic(III) and arsenic(V) species with glutathione, Chem Res Tox 6 (1993), 102-106.
36. 13C NMR spectroscopy and ab initio calculations: Relations to the Hammett parameters and atomic charges, New J Chem 27 (2003), 1115-1123.
37. E. Sletten, J. Sletten and L.H. Jensen, The crystal and molecular structure of 6-mercaptopurine monohydrate, Acta Cryst B25 (1969), 1330-1338.
38. 3, Z Anorg Allg Chem 634 (2008), 436-440.
39. 3As, by octasulfur/ triethylamine and dioxygen, Phosphorus, Sulfur, and Silicon 181 (2006), 413-425.
40. A.I. Vogel, A Textbook of Practical Organic Chemistry, 3rd ed., Longmans, London, 1956, pp. 496, 498-499.
41. T.J. Wallace and A. Schriesheim, Solvent effects in the base-catalyzed oxidation of mercaptans with molecular oxygen, J Org Chem 27 (1962), 1514-1516.
42. T.J.Wallace and A. Schriesheim, The base catalyzed oxidation of aliphatic and aromatic thiols and disulfides to sulphonic acids, Tetrahedron 21 (1965), 2271-2280.