Hexafluorocyclobutene is the
organofluorine compound
Organofluorine chemistry describes the chemistry of organofluorine compounds, organic compounds that contain a carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, ...
with the formula (CF
2)
2(CF)
2. A colorless gas, it is a precursor to a variety of compounds, including
squaric acid
Squaric acid or quadratic acid (so named because its four carbon atoms approximately form a square) is a diprotic organic acid with the chemical formula .
The conjugate base of squaric acid is the hydrogensquarate anion ; and the conjugate base ...
. Hexafluorocyclobutene is prepared in two steps from
chlorotrifluoroethylene
Chlorotrifluoroethylene (CTFE) is a chlorofluorocarbon with chemical formula CFCl=CF2. It is commonly used as a refrigerant in cryogenic applications. CTFE has a carbon-carbon double bond and so can be polymerized to form polychlorotrifluoroethy ...
. The thermal dimerization gives 1,2-dichloro-1,2,3,3,4,4-hexafluorocyclobutane. Dechlorination of the latter gives hexafluorocyclobutene:
:C
4F
6Cl
2 + Zn → C
4F
6 + ZnCl
2
Safety
Reminiscent of
perfluoroisobutene, hexafluorocyclobutene is quite toxic with an LD = 6000 mg/min/m
−3 (mice).
[{{cite book , doi=10.1016/B978-008043405-6/50040-2, chapter=Highly-toxic fluorine compounds, title=Fluorine Chemistry at the Millennium, year=2000, last1=Timperley, first1=Christopher M., pages=499–538, isbn=9780080434056]
See also
*
Hexafluoro-2-butyne
Hexafluoro-2-butyne (HFB) is a fluorocarbon with the chemical structure CF3C≡CCF3. HFB is a particularly electrophilic alkyne, acetylene derivative (chemistry), derivative, and hence a potent dienophile for Diels–Alder reactions.
Synthesis a ...
*
Hexafluorobutadiene
Hexafluorobutadiene is an organofluorine compound
Organofluorine chemistry describes the chemistry of organofluorine compounds, organic compounds that contain a carbon–fluorine bond. Organofluorine compounds find diverse applications ranging f ...
References
Fluorocarbons
Cycloalkenes