trifluoroacetoxy

Trifluoroacetoxy refers to the anion, radical, or functional group derived from trifluoroacetic acid. Its chemical formula is CF3COO. In organic chemistry, the trifluoroacetoxy group is often abbreviated as OC(O)CF3 or OAcCF3. It is characterized by the presence of a trifluoromethyl group (CF3) attached to a carbonyl group. This electron-withdrawing trifluoromethyl group significantly impacts the properties of the trifluoroacetoxy moiety.

The trifluoroacetoxy group can act as a leaving group in various reactions, often exhibiting good leaving group ability due to the inductive effect of the fluorine atoms, which stabilizes the negative charge that develops upon departure. This property makes it useful in certain synthetic transformations. For example, trifluoroacetates can be employed in acylation reactions, where the trifluoroacetyl group is transferred to another molecule. They can also serve as precursors for other trifluoromethyl-containing compounds.

In terms of reactivity, the trifluoroacetoxy group is generally more reactive than its non-fluorinated counterpart, the acetoxy group. This increased reactivity is a consequence of the strong electron-withdrawing nature of the trifluoromethyl group, which makes the carbonyl carbon more electrophilic and the O-CF3 bond more susceptible to cleavage. Trifluoroacetates are often used as protecting groups or as activating groups in specific chemical syntheses.