Oxidation of Arylalkanols by S2O82--CuII

Article abstract of DOI:10.1021/jo00173a027

Products of oxidation of a series of arylalkanols by S2O8^2--Cu^II in acetic acid and acetonitrile are consistent with initial oxidation to aryl radical cations followed by either loss of a benzylic proton or C-C bond scission and subsequent oxidation of intermediate benzylic radicals by Cu^II to final products. 1-Arylalkanols (ArCHOHR)react by both paths, C-C bond scission increasing with stability of the radical R^.. 2-Arylalkanols (ArCH2CHOHR) give chiefly C-C bond scission to benzyl radicals and RCHO.The 3- and 4-arylalkanols undergo chiefly proton loss, and the resulting radicals are oxidized with cyclization to chromans and 2-phenylfurans, respectively, both of which may by oxidized in turn to further products.