title: An electric field-induced change in the selectivity of a metal oxide-catalyzed epoxide rearrangement.
abstract: The rearrangement of cis-stilbene oxide catalyzed by Al(2)O(3) was studied in the presence of interfacial electric fields. Thin films of Al(2)O(3) deposited on Si electrodes were used as the opposing walls of a reaction vessel. Application of a voltage across the electrodes engendered electrochemical double layer formation at the Al(2)O(3)-solution interface. The aldehyde to ketone product ratio of the rearrangement was increased by up to a factor of 63 as the magnitude of the double layer charge density was increased. The results support a field-dipole effect on the selectivity of the catalytic reaction.
authors.affiliation: Stanford University, Department of Chemistry, 337 Campus Drive, Stanford, California 94305, USA.
authors.forename: Craig F
authors.initials: CF
authors.lastname: Gorin
authors.forename: Eugene S
authors.initials: ES
authors.lastname: Beh
authors.forename: Matthew W
authors.initials: MW
authors.lastname: Kanan
mesh_terms: D000537:Aluminum Oxide / Q000737:chemistry*; D002384:Catalysis; D004563:Electrochemistry / Q000379:methods*; D004852:Epoxy Compounds / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry; D013379:Substrate Specificity
chemical_list: D004852:Epoxy Compounds; D058116:Lewis Acids; D000537:Aluminum Oxide