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A novel fluorinating method for the synthesis of α-fluoroketones

✍ Scribed by S. Rozen; Y. Menahem

Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
194 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis

The conventional method for the synthesis of a-fluoroketones was the action of per&oryl fluoride on ketone enamines.

Though this reagent has been successful, mainly with steroidal ketones,') it has well-known and serious limitations. Thus the reagent can beueed only with very electron-rich olefins. En01 acetates for instance hardly react. Often chlorinated or oxygenated compounds are obtained rather than the required fluoroketones. 2) Moreover, the attractivenees of this reagent is reduced by the tendency for its reactions to be accompanied by violent explosiona.

A new method for fluorinating electron rich double bonds was developed with the introduction of fluoroxytrifluoromethane CP3OF. 3) In addition to this reagent, which is expensive and of limited availability, F2 can in particular circumstances act as a source of electronegative fluorine. 4)

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ChemInform Abstract: The Synthesis of α-
ChemInform Abstract: The Synthesis of α-Fluoroketones by 1,4-Additions of Mono- Fluorinated Enamines to Michael Acceptors.
✍ C. F. BRIDGE; D. O'HAGAN 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 30 KB

The Synthesis of α-Fluoroketones by 1,4-Additions of Mono-Fluorinated Enamines to Michael Acceptors. -Stork enamine reactions are used for the preparation of the title compounds which are of bioorganic interest as potential transition state analogues for hydrolytic enzymes. -(BRIDGE,