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
Article Menu

Article Versions

Export Article

Open AccessArticle
Molecules 2012, 17(6), 6625-6632; doi:10.3390/molecules17066625

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

Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan
*
Author to whom correspondence should be addressed.
Received: 7 May 2012 / Revised: 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 (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

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