Advertisement

Oxidations of Organic Compounds Catalyzed by Copper- and Cobalt-Amine Complexes

  • C. R. H. I. de Jonge

Abstract

Selective oxidations of organic substrates catalyzed by transition metal complexes capable of activating oxygen have been of interest since Glaser observed1 more than a hundred years ago that phenylacetylene underwent smooth aerial oxidation to diphenylacetylene when cuprous chloride in ammonia was used as a catalyst. This reaction has since been applied to a wide variety of organic compounds possessing the ethynyl grouping. The Glaser cop-per-amine system has been used in various modifications for many years up to the 1950s when two independant groups found a breakthrough in the oxidation of phenols using a copper-amine complex as a catalyst.2

Keywords

Oxidative Coupling Oxidative Cleavage Phenol Oxidation Anhydrous Potassium Carbonate Alcohol Water 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    C. Glaser, Ber. 2, 422 (1869).Google Scholar
  2. 2.
    W. Brackman and E. Havinga. Rec. Trav. Chim. 74, 937 (1955)CrossRefGoogle Scholar
  3. 3.
    A. S. Hay, H. S. Blanchard, G. F. Endres, and J. W. Eustance, J. Am. Chem. Soc. 81, 6335 (1959).CrossRefGoogle Scholar
  4. 4.
    H. A. P. de Jongh, C. R. H. I. de Jonge, and W. J. Mijs, J. Org. Chem. 36, 3160 (1970).CrossRefGoogle Scholar
  5. 5.
    H. Takahashi, T. Kajimoto and J. Tsuji, Synth. Commun. 2, 181 (1972).CrossRefGoogle Scholar
  6. 6.
    H. C. Volger and W. Brackman, Rec. Trav. Chim. 84, 579 (1965).CrossRefGoogle Scholar
  7. 7.
    H. Hayashi, K. Kawasaki, and T. Murata, Chem. Lett. 1974, 1079.Google Scholar
  8. 8.
    H. M. van Dort and H. J. Geursen, Rec. Trav. Chim. 86. 520 (1967).CrossRefGoogle Scholar
  9. 9.
    C. R. H. I. de Jonge, H. J. Hageman, W. G. B. Huysmans and W. J. Mijs, J. Chem. Soc. Perkin Trans. II 1973, 1276Google Scholar
  10. 10.
    C. R. H. I. de Jonge, H. J. Hageman, G. Hoentjen, and W. J. Mijs, Org. Synth. 57, 78 (1977).Google Scholar
  11. 11.
    E. J. Corey, R. L. Danheiser, S. Chandrasekaran, P. Siret, G. E. Keck, and J. L. Gras, J. Am. Chem. Soc. 100, 8031 (1978).CrossRefGoogle Scholar
  12. 12.
    G. A. Russell, A. G. Bemis, E. J. Geels, E. G. Jansen, and A. J. Move. Adv. Chem. ScL 1, 174 (1968).CrossRefGoogle Scholar
  13. 13.
    G. A. Russell, A. J. Moye, and K. Nagpal, J. Am. Chem. Soc. 84. 4154 (1962).CrossRefGoogle Scholar
  14. 14.
    A. Nishinaga, H. Tomita, and T. Matsuura, Tetrahedron Lett. 1979, 2893.Google Scholar
  15. 15.
    A. S. Hay, J. Org. Chem. 27, 3320 (1962).CrossRefGoogle Scholar
  16. 16.
    F. Bohlmann, Ber. 86, 657 (1953).CrossRefGoogle Scholar
  17. 17.
    Yu. S. Zal’kind and B. W. Fundyler. J. Gen. Chem. (USSR) 9, 1725 (1939); cf. Chem. Ahstr. 34, 3719 (1940).Google Scholar
  18. 18.
    A. Vaitiekunas and F. F. Nord, J. Am. Chem. Soc. 76, 2733 (1954).CrossRefGoogle Scholar
  19. 19.
    A. Chicoisne, G. Duport, and R. Dulou, Bull. Soc. Chim. France 1957, 1232.Google Scholar
  20. 20.
    E. Schjanberg, Ber. 71, 569 (1938).Google Scholar
  21. 21.
    J. F. Arens, H. C. Volger, T. Doornbos, J. Bonnema, J. W. Griedanus and J. H. van der Hende. Rec. Trav. Chim. 75, 1459 (1956).CrossRefGoogle Scholar
  22. 22.
    F. Bohlmann, E. Inhoflen, and J. Poiitt, Ann. Chem. (Liebigs) 604, 207 (1957).CrossRefGoogle Scholar
  23. 23.
    M. Akhtar, T. A. Richards, and B. C. L. Weedon, J. Chem. Soc. 1959, 933. 23.CrossRefGoogle Scholar
  24. 24.
    E. R. H. Jones, H. H. Lee, and M. C. Whiting, J. Chem. Soc. 1960, 341.Google Scholar
  25. 25.
    J. B. Armitage, E. R. H. Jones, and M. C. Whiting, J. Chem. Soc. 1952, 2014.Google Scholar
  26. 26.
    C. L. Cook, E. R. H. Jones, and M. C. Whiting, J. Chem. Soc. 1952, 2883.Google Scholar
  27. 27.
    J. B. Armitage, N. Entwhistle, E. R. H. Jones, and M. C. Whiting, J. Chem. Soc. 1954, 147.Google Scholar
  28. 28.
    P. M. Jacobs and M. A. Davis, J. Org. Chem. 44, 178 (1979).CrossRefGoogle Scholar
  29. 29.
    U. Fritzsche and S. Hunig, Tetrahedron Lett. 1972, 4831.Google Scholar
  30. 30.
    F. Straus, Ann. Chem. (Liebigs) 342, 190 (1905).CrossRefGoogle Scholar
  31. 31.
    C. M. Orlando, Jr., J. Org. Chem. 33, 2516 (1968).CrossRefGoogle Scholar
  32. 32.
    V. V. Karpov and M. L. Khidekel’, J. Org. Chem. (USSR) 3, 1625 (1967).Google Scholar
  33. 33.
    M. S. Kharasch and G. Sosnovsky, Tetrahedron 3, 97 (1958).CrossRefGoogle Scholar
  34. 34.
    R. A. Walton, Quart. Rev. Chem. Soc. 19, 136 (1965).CrossRefGoogle Scholar
  35. 35.
    H. A. P. de Jongh, C. R. H. I. de Jonge, H. J. Sinnige, W. J. de Klein, W. G. B. Huysmans, W. J. Mijs, W. J. van der Hoek, and J. Smidt, J. Org. Chem. 37, 1960 (1972).CrossRefGoogle Scholar
  36. 36.
    V. van Rheenen. Tetrahedron Lett. 1969, 985.Google Scholar
  37. 37.
    J. Tsuji, H. Takayanagi, Tetrahedron 34, 641 (1978).CrossRefGoogle Scholar
  38. 38.
    A. Nishinaga, T. Tojo, and T. Matsuura, J. Chem. Soc. Chem. Commun. 1974, 896.Google Scholar
  39. 39.
    A. Nishinaga, Chem. Lett. 1975, 273.Google Scholar
  40. 40.
    A. Nishinaga, K. Watanabe, and T. Matsuura, Tetrahedron Lett. 1974, 1291.Google Scholar
  41. 41.
    T. Matsuura, K. Watanabe, and A. Nishinaga, Chem. Coomun. 1970, 163.Google Scholar
  42. 42.
    C. R. H. I. de Jonge, unpublished results.Google Scholar
  43. 43.
    Unpublished results obtained by A. J. Leusink and W. Drenth of the Organisch Chemisch Instituut TNO, Utrecht, The Netherlands.Google Scholar
  44. 44.
    J. R. Wasson, T. P. Mitchell, and W. H. Bernard, J. Inorg. Nucl. Chem. 30, 2865 (1968).CrossRefGoogle Scholar
  45. 45.
    H. Diehl and C. C. Hach, Inorg. Syn. 3, 196 (1950).CrossRefGoogle Scholar
  46. 46.
    J. P. Riley, J. Chem. Soc. 1953, 2193.Google Scholar
  47. 47.
    H. A. Stansbury Jr. and W. R. Proops. J. Org. Chem. 27, 320 (1962).CrossRefGoogle Scholar
  48. 48.
    K. P. Callahan and M. F Hawthorne, J. Am. Chem. Soc. 95, 4574 (1973).CrossRefGoogle Scholar
  49. 49.
    R. Eastmond, T. R. Johnson, and D. R. M. Walton, Tetrahedron 28. 4601 (1972).CrossRefGoogle Scholar
  50. 50.
    A. S. Hay, J. Org. Chem. 34, 1160 (1969).CrossRefGoogle Scholar
  51. 51.
    J. B. Armitage, C. L. Cook, N. Entwhistle, E. R. H. Jones, and M. C. Whiting, J. Chem. Soc. 1952, 1998.Google Scholar
  52. 52.
    P. J. Ashworth, E. R. H. Jones, G. H. Mansfield, K. Schögl, J. M. Thompso, and M. C. Whiting, J. Chem. Soc. 1958, 950.Google Scholar
  53. 53.
    R. Paul and S. Tchelitcheff, Bull. Soc. Chim. France 1953. 417.Google Scholar
  54. 54.
    W. Reppe, Ann. Chem. (Licbigs) 596, 1 (1955).Google Scholar
  55. 55.
    Yu. S. Zal’kind, F. B. Fundyler, Ber. 64, 128 (1936).Google Scholar
  56. 56.
    R. Ahmad and B. C. L. Weedon, J. Chem. Soc. 1953, 3286.Google Scholar
  57. 57.
    J. Colonge and Y. Infamet, Bull. Soc. Chim. France 1960. 1914.Google Scholar
  58. 58.
    K. Bowden, I. Heilbron, E. R. H. Jones, and K. H. Sargen, J. Chem. Soc. 1947, 1579.Google Scholar
  59. 59.
    B. L. Shaw and M. C. Whiting, Chem. Ind. 1953, 409.Google Scholar
  60. 60.
    Yu S Zal’kind and I. M. Gverdtsiteli, J. Gen. Chem. (USSR) 9, 971 (1939); cf. Chem. Abstr. 33, 8569 (1939).Google Scholar
  61. 61.
    M. F. Ansell, W. J. Hickinbottom, and A. A. Hyatt. J. Chem. Soc. 1955. 1781.Google Scholar
  62. 62.
    F. Bohlmann and H. Sinn, Ber. 88, 1869 (1955).CrossRefGoogle Scholar
  63. G. F. Hennion and A. L. Perrino, J. Org. Chem. 26, 1073 (1961).CrossRefGoogle Scholar
  64. R. Epsztein and I. Marszak, C R. Acad. Sci. 243, 283 (1956).Google Scholar
  65. 63.
    M. D. Cameron and G. E. Bennett, J. Org. Chem. 22, 557 (1957).CrossRefGoogle Scholar
  66. 64.
    M. Ballester, J. Castaner, J. Riera. I. Taberner, and G Cornet, Tetrahedron Lett. 1977, 2353.Google Scholar
  67. 65.
    R. M. McQuilkin, P. J. Garratt, and F. Sondheimer, J. Am. Chem. Soc. 92, 6682 (1970).CrossRefGoogle Scholar
  68. 66.
    U.S. 3.210,384.Google Scholar
  69. 67.
    C. R. H. I. De Jonge, unpublished results.Google Scholar
  70. 68.
    S. Hibino and S. M. Weinreb, J. Org. Chem. 42, 232 (1977).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1986

Authors and Affiliations

  • C. R. H. I. de Jonge
    • 1
  1. 1.Corporate Research DepartmentAkzo ResearchArnhemThe Netherlands

Personalised recommendations