Ligand and pH influence on manganese-mediated peracetic acid epoxidation of terminal olefins.
[reaction: see text] Nineteen Mn(II) complexes were screened for the catalytic epoxidation of terminal olefins using peracetic acid. Few of these complexes are efficient catalysts at pH < 2, but many are effective at 1 mol % catalyst loading at pH 4. With 0.1 mol % loading, four complexes epoxidize 1-octene in approximately 80% yield in 5 min. The relative reactivity of the catalysts toward different olefins was probed using a multicomponent intermolecular competition reaction.
Chemistry Department, Stanford University, Stanford, California 94305, USA.
Andrew
A
Murphy
Allyson
A
Pace
T Daniel P
TD
Stack
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D008024:Ligands; D008345:Manganese / Q000737:chemistry*; D015394:Molecular Structure; D010463:Peracetic Acid / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D004852:Epoxy Compounds; D008024:Ligands; D008345:Manganese; D010463:Peracetic Acid