Fluonnation with acetyl

The heterocyclic system bimane produces a difluorinated product on fluonnation with acetyl hypofluorite [34] (equation 11)... 

During electrochemical fluorination retention of important functional groups or atoms in molecules is essential. Acyl fluorides and chlorides, but not carboxylic acids and anhydrides (which decarboxylate), survive perfluorination to the perfluorinated acid fluorides, albeit with some cyclization in longer chain (>C4) species [73]. Electrochemical fluonnation of acetyl fluoride produces perfluoro-acetyl fluoride in 36-45% yields [85]. Electrochemical fluonnation of octanoyl chloride results in perfluonnated cyclic ethers as well as perfluorinated octanoyl fluonde. Cyclization decreases as initial substrate concentration increases and has been linked to hydrogen-bonded onium polycations [73], Cyclization is a common phenomenon involving longer (>C4) and branched chains. a-AIkyl-substituted carboxylic acid chlorides, fluorides, and methyl esters produce both the perfluorinated cyclic five- and six-membered ring ethers as well as the perfluorinated acid... 

The aryl tin compounds are better substrates for fluorination because they give high yields of fluonnated aromatics and they may be fluormated with acetyl hypofluorite, cesium fluoroxysulfate, or fluorine [52, 54 (equation 28). Aryl boronic esters react with cesium fluoroxysulfate to produce fluoroaromatics [55] (equation 29). 

The product from fluonnation of sodium acetate is acetyl hypofluorite [64], which IS isolated and characterized [65] The value of this reagent lies in its relative mildness, because it reacts cleanly with most olefins adding the elements of acetoxyl and fluorine [66] Tnfluoroacetyl hypofluorite adds cleanly only to benzylic or electron-rich double bonds... 

Acetyl hypofhiorite is very effective in 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 [51, 52, 53, 54] (equations 25-27). Fluoroxytrifluoromethane fluonnates p-methoxypheny 1 mercuric acetate to give p-fluoroanisole in 86% yield [52]... 

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