Synthesis and reactions of trifluorovinylferrocene

Max Roemer, Dieter Lentz*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

Trifluorovinylferrocene (1) is obtained in high yield by a Stille coupling of iodoferrocene with tributyltrifluorovinylstannane. [2+2] Cycloaddition of 1 yields the cyclobutane derivatives 2a and 2b under mild conditions. At higher temperature a defluoration reaction takes place yielding the cyclobutane derivative 3 under inert conditions whereas in the presence of air and water the cyclobuta-1,2-dion derivative 4 is formed presumably by an unusual hydrolysis of an aliphatic difluoromethylene group. Nucleophilic attack of the CF 2 group of 1 yields specifically the trans isomer of 1,2-Diferrocenyl-1,2-difluoroethene 5. The crystal and molecular structures of 1, 2a, 2b, 3 and 5 were elucidated by X-ray diffraction.

Original languageEnglish
Pages (from-to)4875-4878
Number of pages4
JournalEuropean Journal of Inorganic Chemistry
Volume2008
Issue number31
DOIs
Publication statusPublished - Nov 2008
Externally publishedYes

Keywords

  • Trifluorovinyl group
  • Ferrocene
  • Stille coupling
  • Hexafluorocyclobutane
  • Cycloadditions

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