REGIOSELECTIVITY OF OLEFIN OXIDATION BY IODOSOBENZENE CATALYZED BY METALLOPORPHYRINS: CONTROL BY THE CATALYST

Article abstract of DOI:10.1016/S0040-4020(01)91293-1

The regioselectivity of the oxidation of three monosubstituted olefins, 6-phenoxyhex-1-ene, hex-1-ene and styrene, by iodosobenzene in the presence of various Fe-, Mn- or Cr-tetraaryl-porphyrins, was studied.It was found that, besides epoxides, known products from such systems, allylic alcohols and aldehydes were formed, the latter not being derived from the corresponding epoxides.The relative importance of these reactions greatly depends upon both the metal and porphyrin constituents of the catalyst.More particularly, the competition between epoxidation and allylic hydroxylation can be efficiently controlled by non bonded interactions between the olefin and porphyrin substituents.No hydroxylation of the aromatic rings and no oxidative dealkylation of the ether function was detected.