Simple Oxidation of Thiols with Sodium Iodate under Solid–Solution Biphasic Conditions

(Note: The full text of this document is currently only available in the PDF Version )

Masao Hirano, Sigetaka Yakabe, Ken-ichiro Ando and Takashi Morimoto


Abstract

A variety of aromatic, aliphatic, and alicyclic thiols were readily oxidised with a combination of sodium iodate and chromatographic neutral alumina in hexane to afford the corresponding disulfides in excellent yields under mild and neutral conditions.


References

  1. A. H. Haines, Methods for the Oxidation of Organic Compounds, Academic Press, London Search PubMed (a) Alcohols, Alcohol Derivatives, Alkyl Halides, Nitroalkanes, Alkyl Azides, Carbonyl Compounds, Hydroxyarenes and Aminoarenes, 1988 Search PubMed; (b) Alkanes, Alkenes, Alkynes, and Arenes, 1985 Search PubMed; (c) M. Hudlicky, Oxidations in Organic Chemistry, Am. Chem. Soc., Washington, DC, 1990 Search PubMed; (d) Organic Syntheses by Oxidation with Metal Compounds. ed. W. J. Mijs and C. R. H. I. de Jonge, Plenum Press, New York, 1986 Search PubMed; (e) H. O. House, Modern Synthetic Reactions, W. A. Benjamin, 1972, 2nd edn., ch. 5–7 Search PubMed.
  2. Chemistry of Waste Minimization, ed. J. H. Clark, Chapman and Hall, London, 1995 Search PubMed; J. H. Clark and D. J. Macquarrie, Chem. Soc. Rev., 1996, 303 Search PubMed.
  3. F. A. Andersen, J. Am. Coll. Toxicol., 1995, 14, 231 (Chem. Abstr., 1995, 123, 92848s) Search PubMed.
  4. A. J. Fatiaji, Synthesis, 1974, 229 CrossRef; Ref. 1(c), pp. 30; Ref. 1(e), pp. 353–359.
  5. (a) A. Takuwa, O. Soga, H. Iwamoto and K. Maruyama, Bull. Chem. Soc. Jpn., 1986, 59, 2959 CAS; (b) J. M. Bruce, J. Chem. Soc., 1959, 2366 RSC; (c) T. W. Evans and W. M. Dehn, J. Am. Chem. Soc., 1930, 52, 3647 CrossRef CAS.
  6. Y. Itoh, T. Kakuta, M. Hirano and T. Morimoto, Bull. Chem. Soc. Jpn., 1979, 52, 2169 CAS.
  7. G. Capozzi and G. Modena, in The Chemistry of the Thiol Group, ed. S. Patai, Wiley, London, 1974, ch. 17 Search PubMed; J. March, Advanced Organic Chemistry, Wiley, New York, 1992, 4th edn., pp. 1204–1205 Search PubMed; Ref. 1(c)pp. 250–252.
  8. J. H. Clark, A. P. Kybett and D. J. Macquarrie, Supported Reagents. Preparation, Analysis, and Applications, VCH, New York, 1992 Search PubMed; Preparative Chemistry Using Supported Reagents, ed. P. Laszlo, Academic Press, San Diego, 1987 Search PubMed; Solid Supports and Catalysts in Organic Synthesis, ed. K. Smith, Ellis Horwood, Chichester, 1992 Search PubMed; Supported Reagents and Catalysts in Chemistry, ed. B. K. Hodnett, A. P. Kybett, J. H. Clark and K. Smith, The Royal Society of Chemistry, Cambridge, 1998 Search PubMed.
  9. X. Wu, R. D. Rieke and L. Zhu, Synth. Commun., 1996, 26, 191 CAS; N. Iranpoor, P. Salehi and F. Shiriny, Org. Prep. Proced. Int., 1995, 27, 216 CAS.
  10. Aldrich Catalog Handbook of Fine Chemicals, 1996–1997, pp. 1159 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.