Hexafluorobutadiene is an organofluorine compound with the formula (CF2=CF)2. A colorless gas, it has attracted attention as an etchant in microelectronics. It is the perfluoroanalogue of butadiene.
Preparation It can be prepared by coupling of fluorinated C2 precursors. Addition of iodine monochloride to chlorotrifluoroethylene gives iododichlorotrifluoroethane that can be coupled in the presence of mercury to give 1,2,3,4-tetrchlorohexafluorobutane:
2 CF2Cl−CFCl(I) + Hg → CF2Cl−CFCl−CFCl−CF2Cl + HgI2 Zn-induced dechlorination of this tetrachloride gives the desired perfluorinated diene:
CF2Cl−CFCl−CFCl−CF2Cl + 2 Zn → CF2=CF−CF=CF2 + 2 ZnCl2
Reactions The diene can be rehalogenated, e.g. with bromine upon UV irradiation:
CF2=CF−CF=CF2 + 2 Br2 → CF2Br−CFBr−CFBr−CF2Br Hexafluorobutadiene dimerizes via a [2+2] process at 150 °C to give perfluorinated divinylcyclobutanes. In the presence of the strong Lewis acid aluminium chlorofluoride, hexafluorobutadiene isomerizes to hexafluoro-2-butyne:
CF2=CFCF=CF2 → CF3C≡CCF3
See also Hexafluorocyclobutene, an isomer of C4F6 Hexachlorobutadiene
References




