Trifluoromethyl hypofluorite

Trifluoromethyl hypofluorite is an organofluorine compound with the chemical formula. Its chemical structure resembles methanol, but every hydrogen atom is replaced by a fluorine atom. Trifluoromethyl hypofluorite is a toxic gas at room temperature, exploding when condensed; but in small quantities the compound is useful for certain fluorination reactions in organic chemistry.

Structure

It exists as a colorless gas at room temperature and is highly toxic.
It is a rare example of a hypofluorite, the trifluoromethyl ester of hypofluorous acid.

Generation

It is prepared by the reaction of fluorine gas with carbon monoxide, over a cesium fluoride catalyst:
The reaction is too dangerous for commercial use. The process is highly exothermic, each reagent is either extremely toxic or corrosive, and the product is liable to explode when condensed.

Reactions

The gas hydrolyzes only slowly at neutral pH.
In organic chemistry, the compound adds electrophilic fluorine to multiple bonds. It has been used for the preparation of α-fluoroketones from silyl enol ethers and N-fluoroamides from iminoethers. It directly fluorinates activated arenes.
Behaving like a pseudohalogen, CF₃OF adds to ethylene to give the ether:
With saturated compounds, it usually performs an indiscriminate radical fluorination. But radical traps cause the reaction to instead selectively fluorinate tertiary carbons.