Acetyl Hypofluorite, a New Moderating Carrier of Elemental Flourine and Its Use in Fluorination of 1,3-Dicarbonyl Derivatives

Ori Lerman, Shlomo Rozen

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61 Scopus citations

Abstract

Elemental fluorine and most of the fluoroxy reagents do not react efficiently or cleanly with 1,3-dicarbonyl derivatives or with their corresponding metal enolates even at -75 °C. It has been found that a suspension of sodium acetate in CFC13 or in CFCl3-AcOH, when treated with elemental fluorine, forms a new electrophilic fluorinating reagent, CH3COOF (1), which reacts with substrates without further isolation or purification. This reagent is milder than F2, CF3OF, or CF3COOF and reacts successfully where the other reagents fail. When 1 reacts with 1,3-dicarbonyl compounds, the main product is the 1,3-dioxo-2-fluoro derivative in reasonable yields. When, however, the corresponding sodium enolates were treated with 1, the yields of the monofluoro derivatives were considerably higher. In the case of 1,3-dicarbonyl derivatives with low enol content, only the sodium enolates react with 1 to produce good to very good yields of the corresponding 2-monofluoro derivatives. Thus 1 can be considered as a moderating carrier of the highly reactive F2.

Original languageEnglish
Pages (from-to)724-727
Number of pages4
JournalJournal of Organic Chemistry
Volume48
Issue number5
DOIs
StatePublished - Mar 1983

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