title: The question of electrophilic vs nucleophilic addition of cyclic β-dicarbonyl phenyliodonium ylides: electrophilic cycloaddition of diphenylketene.
abstract: The reaction of β-dicarbonyl phenyliodonium ylides with diphenylketene at room temperature affords mixtures of lactone and aurone derivatives. The initial electrophilic attack of the iodonium ylide on the C(β) position of the diphenylketene, followed by cyclization of the zwitterionic species, and subsequent ejection of iodobenzene, affords the lactone and aurone cycloadducts. Treatment of β-dicarbonyl iodonium ylides with acyl chlorides yields α-chloroenones with good to excellent yields.
authors.affiliation: Department of Chemistry, University of Ioannina, GR-45110 Ioannina, Greece.
authors.forename: Anna
authors.initials: A
authors.lastname: Antos
authors.forename: Yiannis
authors.initials: Y
authors.lastname: Elemes
authors.forename: Adonis
authors.initials: A
authors.lastname: Michaelides
authors.forename: John A
authors.initials: JA
authors.lastname: Nyxas
authors.forename: Stavroula
authors.initials: S
authors.lastname: Skoulika
authors.forename: Lazaros P
authors.initials: LP
authors.lastname: Hadjiarapoglou