Halofluorination of olefins: elucidation of reaction characteristics and applications in labeling with the positron-emitting radionuclide fluorine-18

作者: Yoon Chi Dae , Dale O. Kiesewetter , John A. Katzenellenbogen , Michael R. Kilbourn , Michael J. Welch

DOI: 10.1016/S0022-1139(00)85091-5

关键词: Yield (chemistry)Inorganic chemistryCombinatorial chemistrySolventOlefin fiberChemistryPyridineReaction rate constantHalogenationSolvent effectsReagent

摘要: Abstract Olefin halofluorination involves the in situ generation of a halogen-fluoride reagent and subsequent addition to an olefin. The characteristics this reaction were investigated with three model olefins (allylbenzene, 1-hexene propene) order assess its potential for labeling molecules positron-emitting radionuclide fluorine-18 at no-carrier-added level. most favorable conditions bromofluorination utilized 1,3-dibromo-5,5-dimethyl- hydantoin, dichloromethane as solvent. Halofluorination proceeds rapidly efficiently using either equivalent or substoichiometric quantities fluoride ion; HF/pyridine metal fluorides acid can be used, up equivalents water present. By reaction, allylbenzene was labeled 32% yield, under carrier-added conditions. Thus, we anticipate that will prove very useful other fluorine-18.

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