sulfene

Sulfene is a sulfur-containing organic compound with the chemical formula CH2SO2. It is the simplest known sulfene, a class of compounds characterized by a sulfur dioxide group attached to a methylene group. Sulfenes are highly reactive and transient species, meaning they are difficult to isolate and are typically generated in situ for immediate use in chemical reactions.

The structure of sulfene features a sulfur atom double-bonded to two oxygen atoms and single-bonded to a methylene carbon. This arrangement gives the molecule a bent geometry around the sulfur atom. Due to the electron-withdrawing nature of the oxygen atoms, the hydrogen atoms on the methylene group are acidic, making sulfenes susceptible to nucleophilic attack and deprotonation.

Sulfenes are generally prepared by the dehydrohalogenation of sulfonyl halides, such as methanesulfonyl chloride. This reaction involves the removal of a hydrogen halide molecule, typically using a non-nucleophilic base. The high reactivity of sulfenes means they readily undergo various transformations, including cycloaddition reactions, nucleophilic additions, and polymerization. Their instability makes them challenging to study directly, and much of our understanding comes from trapping experiments and theoretical calculations. Despite their transient nature, sulfenes are valuable intermediates in organic synthesis, enabling the formation of various sulfur-containing heterocycles and other complex molecules.