Electroreductive Ring-Opening of α,β-Epoxy Carbonyl Compounds and Their Homologues through Recyclable Use of Diphenyl Diselenide or Diphenyl Ditelluride as a Mediator

Article abstract of DOI:10.1021/jo00292a032

A novel access to β-hydroxy carbonyl compounds from the corresponding α,β-epoxy compounds has been attained through the recyclable use of diphenyl diselenide or diphenyl ditelluride as an electroreduction mediator in a MeOH-NaClO4-(Pt) system. α,β-Epoxy ketones are converted to the corresponding aldols in the presence of malonic esters.Similarly, α,β-epoxy esters and nitriles can be reduced to the corresponding β-hydroxy compounds in the presence of acetic acid.