Reaction of carbonyl compounds with xenon difluoride in the presence of silicon tetrafluoride

Masanori Tamura*, Yasuhisa Matsukawa, Heng Dao Quan, Junji Mizukado, Akira Sekiya

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

Reaction of various carbonyl compounds with xenon difluoride in the presence of silicon tetrafluoride was investigated. Aromatic aldehyde, ketones, and α-ketoester react with xenon difluoride to give α,α-difluoroalkyl phenyl ethers. However, acid fluoride, ester, acid cyanide, α-ketocarboxylic acid, or thioester do not afford the corresponding products. In the case of cinnamaldehyde, fluorination was accompanied by intramolecular cyclization to afford fluorinated epoxide.

Original languageEnglish
Pages (from-to)705-709
Number of pages5
JournalJournal of Fluorine Chemistry
Volume125
Issue number5
DOIs
Publication statusPublished - May 2004
Externally publishedYes

Keywords

  • Carbonyl compound
  • Cinnamaldehyde
  • Cyclization
  • Fluorination
  • Rearrangement
  • Silicon tetrafluoride
  • Xenon difluoride

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