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 language | English |
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Pages (from-to) | 4875-4878 |
Number of pages | 4 |
Journal | European Journal of Inorganic Chemistry |
Volume | 2008 |
Issue number | 31 |
DOIs | |
Publication status | Published - Nov 2008 |
Externally published | Yes |
Keywords
- Trifluorovinyl group
- Ferrocene
- Stille coupling
- Hexafluorocyclobutane
- Cycloadditions