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
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References
C. Glaser, Ber. 2, 422 (1869).
W. Brackman and E. Havinga. Rec. Trav. Chim. 74, 937 (1955)
A. S. Hay, H. S. Blanchard, G. F. Endres, and J. W. Eustance, J. Am. Chem. Soc. 81, 6335 (1959).
H. A. P. de Jongh, C. R. H. I. de Jonge, and W. J. Mijs, J. Org. Chem. 36, 3160 (1970).
H. Takahashi, T. Kajimoto and J. Tsuji, Synth. Commun. 2, 181 (1972).
H. C. Volger and W. Brackman, Rec. Trav. Chim. 84, 579 (1965).
H. Hayashi, K. Kawasaki, and T. Murata, Chem. Lett. 1974, 1079.
H. M. van Dort and H. J. Geursen, Rec. Trav. Chim. 86. 520 (1967).
C. R. H. I. de Jonge, H. J. Hageman, W. G. B. Huysmans and W. J. Mijs, J. Chem. Soc. Perkin Trans. II 1973, 1276
C. R. H. I. de Jonge, H. J. Hageman, G. Hoentjen, and W. J. Mijs, Org. Synth. 57, 78 (1977).
E. J. Corey, R. L. Danheiser, S. Chandrasekaran, P. Siret, G. E. Keck, and J. L. Gras, J. Am. Chem. Soc. 100, 8031 (1978).
G. A. Russell, A. G. Bemis, E. J. Geels, E. G. Jansen, and A. J. Move. Adv. Chem. ScL 1, 174 (1968).
G. A. Russell, A. J. Moye, and K. Nagpal, J. Am. Chem. Soc. 84. 4154 (1962).
A. Nishinaga, H. Tomita, and T. Matsuura, Tetrahedron Lett. 1979, 2893.
A. S. Hay, J. Org. Chem. 27, 3320 (1962).
F. Bohlmann, Ber. 86, 657 (1953).
Yu. S. Zal’kind and B. W. Fundyler. J. Gen. Chem. (USSR) 9, 1725 (1939); cf. Chem. Ahstr. 34, 3719 (1940).
A. Vaitiekunas and F. F. Nord, J. Am. Chem. Soc. 76, 2733 (1954).
A. Chicoisne, G. Duport, and R. Dulou, Bull. Soc. Chim. France 1957, 1232.
E. Schjanberg, Ber. 71, 569 (1938).
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).
F. Bohlmann, E. Inhoflen, and J. Poiitt, Ann. Chem. (Liebigs) 604, 207 (1957).
M. Akhtar, T. A. Richards, and B. C. L. Weedon, J. Chem. Soc. 1959, 933. 23.
E. R. H. Jones, H. H. Lee, and M. C. Whiting, J. Chem. Soc. 1960, 341.
J. B. Armitage, E. R. H. Jones, and M. C. Whiting, J. Chem. Soc. 1952, 2014.
C. L. Cook, E. R. H. Jones, and M. C. Whiting, J. Chem. Soc. 1952, 2883.
J. B. Armitage, N. Entwhistle, E. R. H. Jones, and M. C. Whiting, J. Chem. Soc. 1954, 147.
P. M. Jacobs and M. A. Davis, J. Org. Chem. 44, 178 (1979).
U. Fritzsche and S. Hunig, Tetrahedron Lett. 1972, 4831.
F. Straus, Ann. Chem. (Liebigs) 342, 190 (1905).
C. M. Orlando, Jr., J. Org. Chem. 33, 2516 (1968).
V. V. Karpov and M. L. Khidekel’, J. Org. Chem. (USSR) 3, 1625 (1967).
M. S. Kharasch and G. Sosnovsky, Tetrahedron 3, 97 (1958).
R. A. Walton, Quart. Rev. Chem. Soc. 19, 136 (1965).
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).
V. van Rheenen. Tetrahedron Lett. 1969, 985.
J. Tsuji, H. Takayanagi, Tetrahedron 34, 641 (1978).
A. Nishinaga, T. Tojo, and T. Matsuura, J. Chem. Soc. Chem. Commun. 1974, 896.
A. Nishinaga, Chem. Lett. 1975, 273.
A. Nishinaga, K. Watanabe, and T. Matsuura, Tetrahedron Lett. 1974, 1291.
T. Matsuura, K. Watanabe, and A. Nishinaga, Chem. Coomun. 1970, 163.
C. R. H. I. de Jonge, unpublished results.
Unpublished results obtained by A. J. Leusink and W. Drenth of the Organisch Chemisch Instituut TNO, Utrecht, The Netherlands.
J. R. Wasson, T. P. Mitchell, and W. H. Bernard, J. Inorg. Nucl. Chem. 30, 2865 (1968).
H. Diehl and C. C. Hach, Inorg. Syn. 3, 196 (1950).
J. P. Riley, J. Chem. Soc. 1953, 2193.
H. A. Stansbury Jr. and W. R. Proops. J. Org. Chem. 27, 320 (1962).
K. P. Callahan and M. F Hawthorne, J. Am. Chem. Soc. 95, 4574 (1973).
R. Eastmond, T. R. Johnson, and D. R. M. Walton, Tetrahedron 28. 4601 (1972).
A. S. Hay, J. Org. Chem. 34, 1160 (1969).
J. B. Armitage, C. L. Cook, N. Entwhistle, E. R. H. Jones, and M. C. Whiting, J. Chem. Soc. 1952, 1998.
P. J. Ashworth, E. R. H. Jones, G. H. Mansfield, K. Schögl, J. M. Thompso, and M. C. Whiting, J. Chem. Soc. 1958, 950.
R. Paul and S. Tchelitcheff, Bull. Soc. Chim. France 1953. 417.
W. Reppe, Ann. Chem. (Licbigs) 596, 1 (1955).
Yu. S. Zal’kind, F. B. Fundyler, Ber. 64, 128 (1936).
R. Ahmad and B. C. L. Weedon, J. Chem. Soc. 1953, 3286.
J. Colonge and Y. Infamet, Bull. Soc. Chim. France 1960. 1914.
K. Bowden, I. Heilbron, E. R. H. Jones, and K. H. Sargen, J. Chem. Soc. 1947, 1579.
B. L. Shaw and M. C. Whiting, Chem. Ind. 1953, 409.
Yu S Zal’kind and I. M. Gverdtsiteli, J. Gen. Chem. (USSR) 9, 971 (1939); cf. Chem. Abstr. 33, 8569 (1939).
M. F. Ansell, W. J. Hickinbottom, and A. A. Hyatt. J. Chem. Soc. 1955. 1781.
F. Bohlmann and H. Sinn, Ber. 88, 1869 (1955).
G. F. Hennion and A. L. Perrino, J. Org. Chem. 26, 1073 (1961).
R. Epsztein and I. Marszak, C R. Acad. Sci. 243, 283 (1956).
M. D. Cameron and G. E. Bennett, J. Org. Chem. 22, 557 (1957).
M. Ballester, J. Castaner, J. Riera. I. Taberner, and G Cornet, Tetrahedron Lett. 1977, 2353.
R. M. McQuilkin, P. J. Garratt, and F. Sondheimer, J. Am. Chem. Soc. 92, 6682 (1970).
U.S. 3.210,384.
C. R. H. I. De Jonge, unpublished results.
S. Hibino and S. M. Weinreb, J. Org. Chem. 42, 232 (1977).
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© 1986 Plenum Press, New York
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de Jonge, C.R.H.I. (1986). Oxidations of Organic Compounds Catalyzed by Copper- and Cobalt-Amine Complexes. In: Mijs, W.J., de Jonge, C.R.H.I. (eds) Organic Syntheses by Oxidation with Metal Compounds. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-2109-5_7
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DOI: https://doi.org/10.1007/978-1-4613-2109-5_7
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