title: The retro-Nazarov reaction.
abstract: Treatment of 2-bromo-4-t-butoxy-2-cyclopentenone with an amine base in refluxing trifluoroethanol afforded a ring-opened product in moderate yield. The mechanism of the reaction has been formulated as a retro-Nazarov reaction in which an oxyallylic cation undergoes ring-opening to a dienone. Several other examples of the reaction have been established through a protocol involving the conjugate addition of an organocuprate to 2-bromo-4-t-butoxy-2-cyclopentenone followed by treatment of the adducts with base in refluxing trifluoroethanol.
authors.affiliation: Department of Chemistry, University of Missouri-Columbia, Columbia, Missouri 65211, USA. harmatam@missouri.edu
authors.forename: Michael
authors.initials: M
authors.lastname: Harmata
authors.forename: Dong Reyoul
authors.initials: DR
authors.lastname: Lee