Metalloporphyrins catalyze polyene-polymers to polyepoxides

Polyene polymers natural rubber (cis-polyisoprene), trans-polyisoprene, and cis-polybutadiene] were transformed to the corresponding polyepoxides which are a polyalcohol and soap precursor. The catalysts used were chloro- or acetato-manganese^(III) tetraphenylporphyrin Mn^III(TPP)Cl or Mn^III(TPP)OAc] in association with two different oxygen donors, sodium hypochloride and iodosylbenzene (Por, unspecified porphyrinato ligand; TPP, 5,10,15,20-tetraphenylporphyrinato ligand). This transformation in either biphasic system, H₂O(aqua)-CH₂Cl₂ or PhIO(solid)-CH₂Cl₂, was monitored by ¹H-NMR and IR spectroscopy. In both cases the transformation to the polyepoxide was completed within a few hours. © 1992 John Wiley & Sons, Inc.