Synergistic oxidation of cyclohexane and hydrogen sulfide under Gif conditions

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

Derek H. R. Barton, Tingsheng Li and John MacKinnon


Abstract

Saturated hydrocarbons and hydrogen sulfide can be synergistically oxidised by oxygen (or air) to give efficiently ketones (and the corresponding alcohols) and sulfur in the presence of a Gif catalyst based on FeII, picolinic acid and 4-tert-butylpyridine with acetonitrile as solvent at room temperature and nearly neutral pH.


References

  1. D. H. R. Barton, B. Hu, D. K. Taylor and R. U. Rojas Wahl, J. Chem. Soc., Perkin Trans. 2, 1996, 1031 RSC.
  2. D. H. R. Barton, B. Hu, T. Li and J. MacKinnon, Tetrahedron Lett., 1996, 37, 8329 CrossRef CAS.
  3. D. H. R. Barton, B. Hu, D. K. Taylor and R. U. Rojas Wahl, New. J. Chem., 1996, 20, 121 Search PubMed.
  4. D. H. R. Barton and A. Sobkowiak, New J. Chem., 1996, 20, 929 Search PubMed and references there cited.
  5. D. H. R. Barton and B. Chabot, Tetrahedron, 1996, 52, 10287 CrossRef CAS.
  6. D. H. R. Barton and D. Doller, Acc. Chem. Res., 1992, 25, 504 CrossRef CAS.
  7. D. H. R. Barton, M. Costas and J. MacKinnon, unpublished results.
  8. V. Schuchardt, W. A. Carvalho and E. V. Spinace, Synlett, 1993, 713 CrossRef CAS.
  9. F. Minisci, F. Fontana, S. Araneo and F. Recupero, J. Chem. Soc., Chem. Commun., 1994, 1823 RSC; Tetrahedron Lett., 1994, 35, 3759 Search PubMed; F. Minisci and F. Fontana, Tetrahedron Lett., 1994, 35, 1427 Search PubMed.
  10. D. H. R. Barton, M. J. Gastiger and W. B. Motherwell, J. Chem. Soc., Chem. Commun., 1983, 41 RSC.
  11. See, for example, G. K. Cook and J. M. Mayer, J. Am. Chem. Soc., 1995, 117, 7139 Search PubMed.
  12. W. Nam and J. S. Valentine, New J. Chem, 1989, 13 Search PubMed; C. Sheu, A. Sobkowiak, L. Zhang, N. Ozbalik, D. H. R. Barton and D. T. Sawyer, J. Am. Chem. Soc., 1989, 111, 8030 CrossRef CAS; C. Sheu, A. Sobkowiak, S. Jeon and D. T. Sawyer, J. Am. Chem. Soc., 1990, 112, 879 CrossRef CAS; C. Sheu, S. A. Rickert, P. Cofre, B. Ross, A. Sobkowiak, D. T. Sawyer and J. R. Kanofsky, J. Am. Chem. Soc., 1990, 112, 1936 CrossRef CAS; C. Sheu and D. T. Sawyer, J. Am. Chem. Soc., 1990, 112, 8212 CrossRef CAS and later papers from the Sawyer group Summarising article: V. Schuchardt, W. A. Carvalho and E. V. Spinace, Synlett, 1993, 713, and earlier papers there cited B. Singh, J. R. Long, G. C. Papaefthymiou and P. Stavropoulos, J. Am. Chem. Soc., 1996, 118, 5824 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.