The Question of Electrophilic vs Nucleophilic Addition of Cyclic beta-Dicarbonyl Phenyliodonium Ylides: Electrophilic Cycloaddition of Diphenylketene

dc.contributor.authorAntos, A.en
dc.contributor.authorElemes, Y.en
dc.contributor.authorMichaelides, A.en
dc.contributor.authorNyxas, J. A.en
dc.contributor.authorSkoulika, S.en
dc.contributor.authorHadjiarapoglou, L. P.en
dc.date.accessioned2015-11-24T16:51:03Z
dc.date.available2015-11-24T16:51:03Z
dc.identifier.issn0022-3263-
dc.identifier.urihttps://olympias.lib.uoi.gr/jspui/handle/123456789/9681
dc.rightsDefault Licence-
dc.subjectc-h insertionen
dc.subjectiodonium ylidesen
dc.subjectefficient synthesisen
dc.subjectrhodium(ii)-catalyzed reactionen
dc.subjectmechanismen
dc.subjectalkenylen
dc.subjectchemistryen
dc.subjectdiketonesen
dc.subjectaciden
dc.titleThe Question of Electrophilic vs Nucleophilic Addition of Cyclic beta-Dicarbonyl Phenyliodonium Ylides: Electrophilic Cycloaddition of Diphenylketeneen
heal.abstractThe reaction of beta-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-beta position of the diphenylketene, followed by cyclization of the zwitterionic species, and subsequent ejection of iodobenzene, affords the lactone and aurone cycloadducts. Treatment of beta-dicarbonyl iodonium ylides with acyl chlorides yields alpha-chloroenones with good to excellent yields.en
heal.accesscampus-
heal.fullTextAvailabilityTRUE-
heal.identifier.primaryDoi 10.1021/Jo3020787-
heal.identifier.secondary<Go to ISI>://000311926100052-
heal.identifier.secondaryhttp://pubs.acs.org/doi/pdfplus/10.1021/jo3020787-
heal.journalNameJournal of Organic Chemistryen
heal.journalTypepeer reviewed-
heal.languageen-
heal.publicationDate2012-
heal.publisherAmerican Chemical Societyen
heal.recordProviderΠανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείαςel
heal.typejournalArticle-
heal.type.elΆρθρο Περιοδικούel
heal.type.enJournal articleen

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