Oxidation of Styrene Derivatives by S2O82--CuII in Acetic Acid and Acetonitrile. Reaction Paths in Oxidations via Radical Cations

Article abstract of DOI:10.1021/ja00336a043

β-Aryl carbonyl compounds are major products in the oxidation of a variety of styrene derivatives by S2O8^2--Cu^II.Evidence is presented that they arise via oxidation to a radical cation, nucleophilic addition of water to give a β-hydroxyalkyl radical, Cu^II 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.