Trifluoromethylsulfonyl

Trifluoromethylsulfonyl (also known as triflyl) is a functional group in organic chemistry. It is represented by the formula -SO2CF3 and is derived from trifluoromethylsulfonic acid. The trifluoromethylsulfonyl group is a strong electrophile, which makes it a useful reagent in organic synthesis.

Structure and Bonding

The trifluoromethylsulfonyl group consists of a sulfur atom bonded to two oxygen atoms and a trifluoromethyl group. The sulfur-oxygen bonds are double bonds, and the sulfur-carbon bond is a single bond. The trifluoromethyl group consists of a carbon atom bonded to three fluorine atoms.

Properties

Trifluoromethylsulfonyl compounds are typically colorless liquids or solids that are stable under normal conditions. They are highly reactive due to the presence of the electrophilic sulfur atom, which can readily accept electrons from a nucleophile.

Applications

Trifluoromethylsulfonyl compounds are used as reagents in organic synthesis. They can act as sulfonylating agents, introducing the trifluoromethylsulfonyl group into other molecules. This can be useful for modifying the properties of these molecules, for example by increasing their acidity or reactivity.

See Also

• Trifluoromethanesulfonic acid
• Sulfonyl group
• Organic synthesis