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

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

Research output: Contribution to journalArticlepeer-review

Abstract

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

Original languageEnglish (US)
Pages (from-to)99-113
Number of pages15
JournalJournal of Fluorine Chemistry
Volume31
Issue number1
DOIs
StatePublished - Feb 1986

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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