Next Article in Journal
Aqueous Fraction of Nephelium ramboutan-ake Rind Induces Mitochondrial-Mediated Apoptosis in HT-29 Human Colorectal Adenocarcinoma Cells
Next Article in Special Issue
Hypervalent Nonbonded Interactions of a Divalent Sulfur Atom. Implications in Protein Architecture and the Functions
Previous Article in Journal
Reversible Low-Light Induced Photoswitching of Crowned Spiropyran-DO3A Complexed with Gadolinium(III) Ions
Molecules 2012, 17(6), 6625-6632; doi:10.3390/molecules17066625
Article

Reaction of Iodonium Ylides of 1,3-Dicarbonyl Compounds with HF Reagents

 and *
Received: 7 May 2012; in revised form: 29 May 2012 / Accepted: 29 May 2012 / Published: 31 May 2012
(This article belongs to the Special Issue Hypervalent Compounds)
Download PDF [247 KB, uploaded 18 June 2014]
Abstract: Reaction of dibenzoylmethane with (diacetoxyiodo)benzene in the presence of KOH in MeCN quantitatively gave the corresponding iodonium ylide, which was treated with a HF reagent to afford the corresponding 2-fluorinated dibenzoylmethane in 14–50% yields. The similar reaction of the iodonium ylides obtained from 1-phenylbutan-1,3-dione, ethyl benzoylacetate, and ethyl p-nitrobenzoylacetate with TEA·3HF gave the corresponding fluorinated products in 17–34% yields. It is suggested that the fluorinated products were formed through the C-protonation of the ylide, followed by displacement with fluoride ion. The same reaction of the iodonium ylide of dibenzoylmethane with concentrated HCl gave the corresponding chlorinated product in 45% yield.
Keywords: iodonium ylide; hypervalent iodine; dibenzoylmethane; 1,3-dicarbonyl compound; fluorination; chlorination iodonium ylide; hypervalent iodine; dibenzoylmethane; 1,3-dicarbonyl compound; fluorination; chlorination
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


MDPI and ACS Style

Gondo, K.; Kitamura, T. Reaction of Iodonium Ylides of 1,3-Dicarbonyl Compounds with HF Reagents. Molecules 2012, 17, 6625-6632.

AMA Style

Gondo K, Kitamura T. Reaction of Iodonium Ylides of 1,3-Dicarbonyl Compounds with HF Reagents. Molecules. 2012; 17(6):6625-6632.

Chicago/Turabian Style

Gondo, Keisuke; Kitamura, Tsugio. 2012. "Reaction of Iodonium Ylides of 1,3-Dicarbonyl Compounds with HF Reagents." Molecules 17, no. 6: 6625-6632.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert