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8320692 
Journal Article 
Polystyrene-Bound Phenylseleninic Acid: Catalytic Oxidations of Olefins, Ketones, and Aromatic Systems 
Taylor, RT; Flood, LA 
1983 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
48 
26 
5160-5164 
English 
A new synthesis of polystyrene-bound phenylseleninic 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 quiñones. Conversion of 1,5-dihydroxynaphthalene into juglone can be realized in 70% yield. © 1983, American Chemical Society. All rights reserved.