The Dissociative Route in the Alkaline Hydrolysis of Aryl 4-Hydroxy-β-styrenesulfonates

Abstract

Reactivity comparisons, activation parameters, and the substituent effect in the leaving group indicate that the hydrolysis of title esters in moderately to strongly alkaline aqueous solution follows a dissociative pathway with the probable participation of an extended sulfoquinone (thioquinone dioxide) intermediate. The interposition of a vinylene group between the internal nucleophile and the reaction site favors the elimination−addition process. Present results further suggest the high tendency of suitably substituted sulfonyl derivatives to hydrolyze through dissociative mechanism.