Oxidation of Styrene Derivatives by S2O82--CuII in Acetic Acid and Acetonitrile. Reaction Paths in Oxidations via Radical Cations
β-Aryl carbonyl compounds are major products in the oxidation of a variety of styrene derivatives by S2O82--CuII.Evidence is presented that they arise via oxidation to a radical cation, nucleophilic addition of water to give a β-hydroxyalkyl radical, CuII oxidation to epoxide, and finally acid-catalyzed rearrangement.Data on oxidation of alkyl aromatics with additional functional groups are presented.With ether and amino groups, oxidation occurs at the functional group even when it is remote from the aryl nucleus.These and previous data are summarized to give a coherent picture of the various paths by which aryl side chains may be degraded via initial radical cation intermediates.
OXIDATION BY COBALT(III) ACETATE. PART 6. A NOVEL SYNTHESIS OF THE GLYCOL MONOACETATES FROM AROMATIC OLEFINS IN WET ACETIC ACID
Oxidation of various aryl-conjugated olefins with cobalt(III) acetate in wet acetic acid under nitrogen affords the glycol monoacetates in moderate to good yields.None of the phenyl rearrangement product is formed in the present reactions.These results are best interpreted by assuming the formation of a Co-co-ordinated intermediate.
Hirano, Masao,Morimoto, Takashi
p. 1033 - 1036
(2007/10/02)
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