sulfinylsubstituted

Sulfinylsubstituted refers to molecules in which a sulfinyl group is installed as a substituent on a parent framework. The sulfinyl group comprises a sulfur atom double bonded to one oxygen and bonded to the rest of the molecule, typically through the sulfur atom, giving sulfur an oxidation state of +4. When the sulfinyl group is attached to carbon, the fragment is encountered as a sulfoxide derivative of the parent compound; sulfinyl substituents can also be attached to heteroatoms.

In IUPAC nomenclature, the substituent is called sulfinyl, and compound names may feature prefixes such as methylsulfinyl- or phenylsulfinyl-. The term is widely used in the chemistry of sulfoxides and in synthetic contexts where a sulfinyl group acts as a activating or directing moiety. A well-known application is the tert-butylsulfinyl group, used as a chiral auxiliary in asymmetric synthesis, where the sulfinyl group assists in achieving stereochemical control.

Preparation and reactions: Sulfinyl substituents are commonly introduced by oxidation of sulfides (thioethers) to sulfoxides, using oxidants such as hydrogen peroxide or mCPBA. They can be reduced back to sulfides or further oxidized to sulfones. Sulfinyl-containing compounds participate in typical sulfoxide chemistry, including sulfoxide–olefin reactions and rearrangements under activation, such as Pummerer-type transformations.

See also: sulfoxide, sulfone, sulfinyl chloride, tert-butanesulfinyl group, Ellman sulfinamide.