The question of electrophilic vs. nucleophilic addition of cyclic Ξ²-dicarbonyl phenyliodonium ylides: Electrophilic cycloaddition of diphenylketene (Journal article)

Antos, A./ Elemes, Y./ Michaelides, A./ Nyxas, J. A./ Skoulika, S./ Hadjiarapoglou, L. P.


The reaction of Ξ²-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 CΞ² position of the diphenylketene, followed by cyclization of the zwitterionic species, and subsequent ejection of iodobenzene, affords the lactone and aurone cycloadducts. Treatment of Ξ²-dicarbonyl iodonium ylides with acyl chlorides yields Ξ±-chloroenones with good to excellent yields.
Institution and School/Department of submitter: Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας
URI: http://olympias.lib.uoi.gr/jspui/handle/123456789/9682
Link: http://pubs.acs.org/doi/abs/10.1021/jo3020787
Publisher: American Chemical Society
Appears in Collections:Άρθρα σε επιστημονικά περιοδικά ( Ανοικτά)

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