arylisulfonates

Aryl sulfonates are organic compounds containing the functional group ArSO3R, where Ar represents an aromatic ring and R is typically an alkyl or aryl group. These compounds are derived from sulfonic acids, specifically aromatic sulfonic acids. The aryl sulfonate moiety, ArSO3-, is a good leaving group, making aryl sulfonates valuable intermediates in organic synthesis.

The synthesis of aryl sulfonates can be achieved through various methods. One common approach involves the reaction of an aromatic alcohol or phenol with an arenesulfonyl halide, such as benzenesulfonyl chloride, in the presence of a base. Alternatively, aryl sulfonates can be prepared by esterification of sulfonic acids with alcohols. The properties of aryl sulfonates vary depending on the nature of the aromatic ring and the R group. They are generally stable compounds, though they can undergo hydrolysis under acidic or basic conditions to regenerate the sulfonic acid and the corresponding alcohol or phenol.

Due to the excellent leaving group ability of the sulfonate anion, aryl sulfonates are widely employed in nucleophilic substitution reactions. They are often used to activate hydroxyl groups for displacement by various nucleophiles, facilitating the formation of new carbon-heteroatom bonds. This reactivity makes them important in the synthesis of pharmaceuticals, dyes, and other fine chemicals. For example, they can be used to convert alcohols into alkyl halides or amines. The versatility and predictable reactivity of aryl sulfonates contribute to their widespread use in synthetic organic chemistry.