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Synlett 1999; 1999(9): 1375-1378
DOI: 10.1055/s-1999-2840
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Efficient Synthesis of 4-Fluorocyclohexa-2,5-dienone Derivatives Using N-Fluoro-1,4-diazoniabicyclo[2.2.2]octane Salt Analogues

Stojan Stavber* , Marjan Jereb, Marko Zupan
  • *Laboratory for Organic and Bioorganic Chemistry, "Josef Stefan" Institute and Department of Chemistry, University of Ljubljana, Jamova 39, 1000 Ljubljana, SLOVENIA; Fax +38 66 11 77-38 11; E-mail: stojan.stavber@ijs.si
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Publication Date:
31 December 1999 (online)

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4-Fluorocyclohexa-2,5-dienone derivatives were obtained in high yield by reaction of para substituted phenols with 1-fluoro-4-chloromethyl-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoro-borate) (1a, SelectfluorTM F-TEDA-BF4) or its 4-hydroxy analogue (1b, AccufluorTM NFTh) in acetonitrile. Estrogen steroids were readily converted to 10β-fluoro-1,4-estradiene-3-one derivatives in high yields.

fluorinated ketones - halogenation - phenols - steroids