Xenon difluoride fluonnation

Xenon difluoride has been used to oxidize a number of antimony compounds [102, 109] in yields ranging from 73 to 98%. Elemental fluorine oxidized tris(pen-tafluorophenyl)stibine to tris(pentafluorophenyl)stibine difluoride in 98% yield [706]. Oxidative fluonnation of stibines has also been accomplished with iodine pentafluoride [707]. 

Pentafluorophenylditelluridc yields 79-80% pentafluorophenyltellunum tri fluoride on treatment with fluorine or xenon difluoride [105] The fluonnated tetravalent tellurium can be further oxidized to hexavalent tellurium with either xenon difluoride [/22] or fluorine [123]... 

Xenon difluoride may be used as the pure reagent or as a graphi te intercalate for the effective fluonnation of polynuclear aromatics [86 87] (equations 49 and 50)... 

Carboxylic acids react with xenon difluoride to produce unstable xenon esters The esters decarboxylate to produce free radical intermediates, which undergo fluonnation or reaction with the solvent system Thus aliphatic acids decarboxylate to produce mainly fluoroalkanes or products from abstraction of hydrogen from the solvent Perfluoro acids decarboxylate in the presence of aromatic substrates to give perfluoroalkyl aromatics Aromatic and vinylic acids do not decarboxylate [91] (equation 51)... 

Xenon difluoride reaction with nitro enolates provides a useful entry into a wide variety of fluonnated synthetic intermediates [91 92] (equation 52)... 

Silyl enol ethers are fluonnated in high yields with xenon difluoride [62 93, 94 95] Applications of this reaction to the preparation of fluonnated... 

On the other hand, oxidizing fluonnating agents like silver difluoride, xenon difluoride, or bromine trifluoride replace one chlorine group and then cleave the sulfur-nitrogen bond [56],... 

Diselenides can also be oxidatively fluonnated, as shown in equation 18 [775, 779]. Benzene selenyl fluoride is postulated as an intermediate during the fluo-roselenation of alkenes with diphenyl diselemde and xenon difluoride [73, 120]... 

Xenon difluoride [4, 5, 7, S, 10] is a white crystalline material obtained through the combination of fluorine and xenon m the presence of light The reagent is commercially available and possesses a relatively long shelf-life when stored cold (freezer) Xenon difluoride is very effective for small-scale fluonnation of alkenes and activated nucleophilic substrates. The reactions are usually conducted between 0 °C and room temperature in chloroform or methylene chlonde solutions Hydrogen fluoride catalysis is sometimes helpful Xenon difluoride reacts in a manner that usually involves some complexation between the substrate and reagent followed by the formation of radical and radical cation intermediates... 

Preparation of 2-Fluoro-4-methylacetanilide, 166 Fluorination with N-terr-Butyl-N-fluorobenzenesulfonamide Preparation of 1-Fluoro-l-octene, 166 Fluonnation with N-Fluoro-2,4,6-tnmethylpyridinium Triflate Preparation of Diethyl Fluorophenylmalonate, 166 Fluorination with Xenon Difluoride... 

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