Fluoroxytrifluoromethane fluorination with

Acetyl hypofluorite is very effective m the fluorination of the aryl-metal (Hg, Ge, or Si) bond, but yields are frequently low. With aryl silicon compounds some competition exists for replacement of an aromatic hydrogen [5i, 52, 55, 54] (equations 25-27). Fluoroxytrifluoromethane fluorinates p-methoxypheny 1 mercuric acetate to givep-fluoroanisole in 86% yield [52]... 

Fluoroxytrifluoromethane, a source of electrophilic fluorine, has recently been employed by Barton et ah for the fluorination of unsaturated steroids.143,144 It is more reactive than perchloryl fluoride and therefore not without danger. It forms, for instance, a highly explosive product with pyridine.143 Like perchloryl fluoride it reacts with enol ethers, esters and enamines, but at lower temperature (— 78°) to yield the fluorinated ketones as well as addition... 

The /V-fluoroamide reactants were initially prepared by fluormation of amides with fluoroxytrifluoromethane [63 Current methods involve the direct fluorination of amide reagents with elemental fluorine under a variety of conditions [48, 64, 65, 66, 67, 68, 69, 71, 72, 73, 74, 76, 81, 82] (Tables 3a and 3b)... 

Reactions of Enol Derivatives and Enamines.—Enolic acetates are transformed into fluoro-ketones by the action of fluoroxytrifluoromethane, a source of electrophilic fluorine (Scheme 10)/ Peroxylauric acid reacted with the enol... 

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