Electrophilic Fluorination of Unsaturated Systems with the Recently Developed Acetyl Hypofluorite

Shlomo Rozen, Ori Lerman, Moshe Kol, David Hebel

Research output: Contribution to journalArticlepeer-review

Abstract

Acetyl hypofluorite (AcOF, 1) is a relatively new reagent which is prepared in situ from F2 and is an excellent source for electrophilic fluorine. Unlike the other known fluoroxy reagents, it reacts smoothly and quickly at -78 °C with many types of olefins to produce acetylated fluorohydrins. It is particularly important as a major tool for introducing the 18F radio isotope into biologically interesting systems. AcOF has been added to arylethenes, isolated aliphatic double bonds, and steroidal olefins with absolute regiospecificity (Markovnikov mode) and good stereoselectivity (syn addition). The more deactivated enones react with 1 with full regio-and stereospecificity, providing they are located in rigid systems or conjugated to an aromatic ring. Other enones, as well as acetylenes, seem to be less reactive when treated with 1. Raising the temperature usually results either in the destruction of the substrate due to thermal radical decomposition of 1 or in full recovery of the starting material. Electron-rich double bonds such as enol acetates react with 1 very rapidly, and after short treatment with base the corresponding α-fluorcr ketones are obtained in good yields.

Original languageEnglish
Pages (from-to)4753-4758
Number of pages6
JournalJournal of Organic Chemistry
Volume50
Issue number24
DOIs
StatePublished - Nov 1985

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