Selective Oxidations of Olefins Catalyzed By Platinum(II) Complexes - Use of Tert-butyl Hydroperoxide and Potassium Caroate As Oxidants - Ketone Vs Epoxide Formation

Four low-cost oxidants have been tested in the oxidation of olefins catalyzed by either [(diphoe)Pt(CF3)(CH2Cl2)]BF4or (diphoe)Pt(CF3)(OH) (diphoe = m-l,2-bis(diphenylphosphino)ethylene) under mild conditions. These include sodium hypochlorite, sodium perborate, tert-butyl hydroperoxide, and potassium hydroperoxysulfate (caroate). While the first two are inactive, with the second two, selective ketonization of the olefin or selective epoxidation (including terminal olefins) can be obtained. A discussion is also included concerning the origin of selectivity in this class of catalysts based essentially on steric factors. © 1989, American Chemical Society. All rights reserved.