Elemental fluorine - Part 18. Selective direct fluorination of 1,3-ketoesters and 1,3-diketones using gas/liquid microreactor technology

Chambers, R.D.; Fox, M.A.; Sandford, G.

Abstract

1,3-Ketoesters and 1,3-diketones react with fluorine gas, using Durham multichannel modular microreactor technology, on a preparatively useful scale. High conversions and yields of monofluorinated products were obtained. A consideration of the mechanism of fluorination of dicarbonyl systems provides a rationale of the scope and limitations of the use of microreactor technology for such direct fluorination processes. We conclude that it is especially appropriate for the fluorination of diketones and ketoesters that exist mainly in the enol form at equilibrium and/or undergo rapid keto - enol interconversion. A one-stage route to fluoroketones from ketoesters was achieved by allowing the crude product mixture obtained from the fluorination of the ketoesters to stand for a period of time before reaction work-up.

Citation

Chambers, R., Fox, M., & Sandford, G. (2005). Elemental fluorine - Part 18. Selective direct fluorination of 1,3-ketoesters and 1,3-diketones using gas/liquid microreactor technology. Lab on a Chip, 5(10), 1132-1139. https://doi.org/10.1039/b504675k

• Journal Article Type: Article
• Publication Date: Aug 15, 2005
• Deposit Date: Apr 26, 2007
• Journal: Lab on a Chip
• Print ISSN: 1473-0197
• Electronic ISSN: 1473-0189
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 5
• Issue: 10
• Pages: 1132-1139
• DOI: https://doi.org/10.1039/b504675k
• Public URL: https://durham-repository.worktribe.com/output/1602232