By Roger A. Sheldon
Metal-Catalyzed Oxidations of natural Compounds
summary: Metal-Catalyzed Oxidations of natural Compounds
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Extra info for Metal-catalyzed Oxidations of Organic Compounds. Mechanistic Principles and Synthetic Methodology Including Biochemical Processes
Sample text
Cr" ► R O + CrmOH ► ROCr 111 (33) (34) The unavailability of a convenient route for regeneration of the Cr(II) precludes a catalytic process. Copper(I) complexes similarly reduce alkyl hydroperoxides to the corresponding alcohols, but a catalytic process is possible 40 3. , RO- + R H 11 R'. , RC(CH 3 ) 2 0 ► R- + ( C H 3 ) 2 C = 0 (37) In view of the low redox potential of the Cu(II)/Cu(I) couple, regeneration of Cu(I) with the hydroperoxide, Cun + R0 2 H ► CuI + R 0 2 - + H + (38) is less likely.
Skellon, Chem. Ind. {London) p. 629 (1951); p. 1047 (1953). 7. J. L. Bolland, Q. , Chem. Soc. 3, 1 (1949). 8. L. Bateman, Q. , Chem. Soc. 8, 147 (1954). 9. H. Hock and B. Lang, Chem. Ber. 77, 257 (1944). 10. L. Reich and S. S. " Dekker, New York, 1969. 11. N. M. Emanuel, E. T. Denisov, and Z. K. Maizus, "Liquid Phase Oxidation of Hydrocarbons" (B. J. ). Plenum, New York, 1967. References 31 12. N. M. " Pergamon, Oxford, 1965. 13. E. T. Denisov and N. M. Emanuel, Russ. Chem. Rev. 29, 645 (1960).
A number of other metal complexes, including those of cerium, copper, cobalt, manganese, and silver, 11-17 also decompose hydrogen peroxide via reactions analogous to eqs 8-12. B. Alkyl Hydroperoxides The metal-catalyzed homolytic decomposition of alkyl hydroperoxidic intermediates is the most common pathway for the catalysis of liquid-phase autoxidations. Information concerning the roles of metal complexes in oxidations has been gained from the separate studies of their interactions with alkyl hydroperoxides under nonautoxidizing conditions.