sulfenes

Sulfenes are a class of organic compounds with the general formula R1R2C=SO2. They are highly reactive and have not been isolated in pure form. Their existence is primarily inferred from their participation in chemical reactions. Sulfenes are considered the sulfur analogs of sulfones and are closely related to sulfenes.

The transient nature of sulfenes makes their study challenging. They are typically generated in situ, meaning they are produced and immediately react within the same reaction mixture. Common methods for generating sulfenes involve the dehydrohalogenation of sulfonyl halides or the oxidation of thiiranes. The highly electrophilic sulfur atom in the SO2 group is a key feature that drives their reactivity.

Sulfenes can undergo a variety of reactions, including cycloadditions, nucleophilic additions, and rearrangements. For instance, they can react with dienes in Diels-Alder-like reactions or with nucleophiles such as amines and alcohols. The products of these reactions often provide evidence for the fleeting existence of the sulfene intermediate. Despite their instability, the study of sulfenes is important for understanding reaction mechanisms and for potentially developing new synthetic methodologies.