Trifluoroacetyl hypofluorite

Acetyl hypobromite, 0729 Acetyl hypofluorite, 0751 Caesium fluoroxysulfate, 4256 Chlorodifluoroacetyl hypochlorite, 0603 Difluoroacetyl hypochlorite, 0653 Fluorine fluorosulfate, 4324 Heptafluorobutyryl hypochlorite, 1352 Heptafluorobutyryl hypofluorite, 1369 Hexafluoroglutaryl dihypochlorite, 1806 Pentafluoropropionyl hypochlorite, 1034 Pentafluoropropionyl hypofluorite, 1056 Propionyl hypobromite, 1154 Rubidium fluoroxysulfate, 4309 Trifluoroacetyl hypochlorite, 0594 Trifluoroacetyl hypofluorite, 0633... 

Trifluoroacetyl hypofluorite is the main product in the low-temperature fluorination of sodium trifluoroacetate in suspension in an inert solvent, and can be further transformed to pentafluoro-(fluoroxy)ethane.2 In some cases, the reaction mixture of up to four reactive products [fluoroxy, bis(fluoroxy) and acyl hypofluorites], formed in reactions with various acid salts, c.g. 5, has been directly used for the fluorination of organic molecules.1 " 5... 

Low-temperature fluorination of sodium acetate in suspension gives a mixture of acetyl hypo-fluorite (AcOF, 1, R = Me) and alkyl hypofluorite the crude mixture can be used, in some cases, directly for the introduction of fluorine into organic molecules. The course of the reaction strongly depends on the reaction conditions and, when the fluoride anion is quenched with hydrogen fluoride or water, trifluoroacetyl hypofluorite (1, R = CF3), 3 acetyl hypofluorite (1, R = Me) and long-chain acid fluorites are obtained.4-6 On the other hand, an excess of fluorine can lead to the formation of alkyl fluoroxy compounds 2 or geminal bis(fluoroxy) products 3. 

Acetyl hypofluorite appears to be a milder reagent than trifluoroacetyl hypofluorite in the fluorination of alkenes and acetylenes. Acetyl hypofluorite undergoes addition to the C = C bond in the fluorination of cyclohexene the ij f7-adduct 4 is obtained in 60% yield, while the reaction with dodec-l-ene gives 2-acctoxy-l-fluorododccanc (5) in 30% yield.10... 

The effect of the reagent structure on the fluorination of phenyl-substituted alkenes 6 has been studied in great detail and the higher svn addition observed with trifluoroacetyl hypofluorite in comparison with acetyl hypofluorite explained on the basis of an intermediately formed... 

Reaction of acetyl hypofluorite with 5//-dibenzo[n. r/]cyclohepten-5-one gives the. vm-adduct 8 trifluoroacetyl hypofluorite appears to be too reactive and only tars are produced. 0... 

Enol acetates, oxo esters, nilroalkenes33 and sodium salts of various esters have been successfully converted into fluoro ketones and esters by acetyl hypofluorite, trifluoroacetyl hypofluorite or mixtures containing acetyl hypofluorite and fluoroxy compounds.3 4 -10-12-13 Examples are the formation of l-fluoro-l,3-diphenylacetone (12), a-fluoro-/i-oxo esters 13, a-fluoro ketones 14 and 15. ethyl l-fluoro-2-oxocyclopentanecarboxylate (16), and 2-fluoromalonate 17. 

Reactions with acetylenes have been much less intensively studied, but important and large differences between trifluoromethyl hypofluorite and trifluoroacetyl hypofluorite have been observed.2 An example of the reactivity of trifluoroacetyl hypofluorite with acetylenes is given by the reaction with 1,2-diphenylacetylene (23) acetyl hypofluorite is unreactive even at room temperature.10... 

The product from fluorination 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] Trifluoroacetyl hypofluorite adds cleanly only to benzylic or electron-rich double bonds... 

Af-Trifluoroacetoxy-2,4-dinitroaniline, 2887 Trifluoroacetyl azide, 0623 2-Trifluoroacetyl-1,3,4-dioxazalone, 1044 0-Trifluoroacetyl-5-fluoroformyl thioperoxide, 1047 Trifluoroacetyl hypochlorite, 0591 Trifluoroacetyl hypofluorite, 0629 Trifluoroacetyhminoiodobenzene, 2898 Trifluoroacetyl nitrite, 0622 Trifluoroacetyl trifluoromethanesulfonate, 1054 Trifluoroacryloyl fluoride, 1046... 

Acetyl hypobromite, 0725 Acetyl hypofluorite, 0748 Caesium fluoroxysulfate, 4250 Chlorodifluoroacetyl hypochlorite, 0600 Difluoroacetyl hypochlorite, 0649 Fluorine fluorosulfate, 4318 Heptafluorobutyryl hypochlorite, 1348 Heptafluorobutyryl hypofluorite, 1365 Hexafluoroglutaryl dihypochlorite, 1800 Pentafluoropropionyl hypochlorite, 1030 Pentafluoropropionyl hypofluorite, 1053 Propionyl hypobromite, 1150 Rubidium fluoroxysulfate, 4303 Trifluoroacetyl hypochlorite, 0591 Trifluoroacetyl hypofluorite, 0629 See Acetyl hypobromite, Propionyl hypobromite... 

SAFETY PROFILE Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. Human teratogenic effects by ingestion developmental abnormalities of the endocrine system. Experimental teratogenic and reproductive effects. Mutation data reported. Explosive reaction with charcoal + ozone, trifluoroacetyl hypofluorite, fluorine perchlorate. Violent reaction or ignition on contact with diazonium salts, diisopropyl peroxydicarbonate, bromine pentafluoride, chlorine trifluoride. Incompatible with oxidants, BrFs, FCIO, metallic salts, calomel. When heated to decomposition it emits very toxic fumes of K20 and I . See also IODIDES. 

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