Journal of the American Chemical Society p. 5712 - 5716 (1985)
Update date:2022-08-23
Topics:
Sugimoto, Hiroshi
Sawyer, Donald T.
Solutions of Fe(II)(MeCN)4(ClO4)2 in dry acetonitrile (MeCN) catalyze the rapid disproportionation of H2O2 to O2 and H2O, but all of the catalyst remains in the Fe(II) oxidation state.In the presence of organic substrates such as 1,4-cyclohexadiene, 1,2-diphenylhydrazine, catechols, and thiols, the Fe(II)-H2O2/MeCN system yields dehydrogenated products (PhH, PhN=NPh, quinones, and RSSR) with conversion efficiencies that range from 100 percent to 17 percent.Although the Fe(II) catalyst does not promote the disproportionation of Me3COOH or m-ClC6H4C(O)OOH, these hydroperoxides are activated for the dehydrogenation of organic substrates.With substrates such as alcohols, aldehydes, methylstyrene, thioethers, sulfoxides, and phosphines, the Fe(II)(H2O2)(2+) adduct promotes their monooxygenation to aldehydes, carboxylic acids, epoxide, sulfoxides, sulfones, and phosphine oxides, respectively: Fe(II) + H2O2 -> Fe(II)(H2O2)(2+) + RH -> Fe(II) + ROH + H2O.The reaction efficiencies for the group of substrates with the Fe(II) adducts that are formed by H2O2, Me3COOH, and m-ClC6H4C(O)OOH have been evaluated.Also, the reaction rates for the substrate-
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