Rhodium-catalyzed oxidation of organic compounds with t-butyl hydroperoxide

Article abstract of DOI:10.1016/0022-328X(88)80247-X

The metal-catalyzed oxidation of organic compounds with t-butyl hydroperoxide (TBHP) and RhCl(PPh3)3 and Rh⁺(diphos) has been investigated.Under appropriate conditions both catalysts give identical results: anthracene is converted into anthraquinone, 1-octene into 2-octanone, and 1-phenylethanol into acetophenone, with 95 to 100percent isolated yields.The phosphine ligands of the catalysts are rapidly attacked during the oxidations, but this does not decrease the activity of the catalytic system.The formation of 2-octanone from 1-octene is believed to be due to a metal-centered mechanism rather than to a free radical pathway.The same mechanism should apply to the oxidation of anthracene and 1-phenylethanol.