The Question of Electrophilic vs Nucleophilic Addition of Cyclic β‑Dicarbonyl Phenyliodonium Ylides: Electrophilic Cycloaddition of Diphenylketene

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 Cβ position of the diphenylketene, followed by cyclization of the zwitterionic species, and sub...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-12, Vol.77 (23), p.10949-10954
Main Authors: Antos, Anna, Elemes, Yiannis, Michaelides, Adonis, Nyxas, John, A, Skoulika, Stavroula, Hadjiarapoglou, Lazaros P
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary: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 Cβ 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo3020787