Polystyrene-Bound Phenylselenic Acid: Catalytic Oxydations of Olefins, Ketones, and Aromatic Systems

Article abstract of DOI:10.1021/jo00174a003

A new synthesis of polystyrene-bound phenylselenic acid, from reaction of mercurated polystyrene and selenium dioxide, is described.A triphasic system of the polymer (in catalytic amounts), aqueous hydrogen peroxide, and dichloromethane is shown to be an effective medium for the conversion of olefins into trans diols and ketones into esters.A biphasic system of the polymer and tert-butyl hydroperoxide in refluxing chloroform effects the selective oxidation of benzylic alcohols to the carbonyl species.In a similar catalytic system hydroxy aromatic compounds can be converted into quinones.Conversion of 1,5-dihydroxynaphthalene into juglone can be realized in 70percent yield.