zenesulf

Sulfenes are a class of organic compounds with the general formula R1R2C=SO2, where R1 and R2 are hydrogen atoms or organic substituents. They are characterized by a carbon-sulfur double bond where the sulfur atom is also bonded to two oxygen atoms, forming a sulfonyl group. Sulfenes are highly reactive and often transient intermediates in organic reactions.

The simplest sulfene is CH2=SO2. Due to their instability, sulfenes are rarely isolated and are typically generated in situ. They are usually prepared by the dehydrohalogenation of alkanesulfonyl chlorides or by the oxidation of thiiranes. Another common method involves the thermolysis of cyclic sulfones or the reaction of sulfur dioxide with carbenes.

Sulfenes readily undergo a variety of reactions, including cycloaddition reactions with dienes and dipolarophiles. They can also react with nucleophiles, leading to the formation of sulfinic acids or their derivatives. The reactivity of sulfenes makes them valuable synthons in organic chemistry, enabling the formation of various sulfur-containing heterocycles and other complex molecules. Research into sulfene chemistry continues to explore their synthetic potential and understand their reaction mechanisms.