Arylsulfonate-Based Nucleophile Assisting Leaving Groups

The synthesis and unique reactivity of a series of arylsulfonate-based nucleophile assisting leaving
groups (NALG) containing oligomeric ether units (including crown ethers) attached to the
arylsulfonyl ring in the ortho orientation are described. The reactions of a variety of these ether-containing alkyl sulfonates with metal halides proceeded at substantially greater rates than
electronically similar sulfonates. These ether-containing leaving groups also displayed marked
selectivity for lithium halides relative to the corresponding sodium and potassium salts in
nucleophilic displacement reactions.