Abstract: Sulfonate leaving groups include a cation chelating moiety, e.g. a polyether or crown ether. The chelating moiety stabilizes the sulfonate leaving group by forming a complex with a cation of a cation-nucleophile combination. The stabilized leaving group is more easily displaced under many conditions than are standard arylsulfonate leaving groups such as the toxyl group. The chelating moiety also favors certain cations depending on the identity of the moiety thereby enhancing the reaction rate with nucleophilic salts containing the preferred cation. Use of the inventive leaving groups results in improved yields, decreased reaction times and improved product purity.

Abstract: Sulfonate leaving groups include a cation chelating moiety, e.g. a polyether or crown ether. The chelating moiety stabilizes the sulfonate leaving group by forming a complex with a cation of a cation-nucleophile combination. The stabilized leaving group is more easily displaced under many conditions than are standard arylsulfonate leaving groups such as the toxyl group. The chelating moiety also favors certain cations depending on the identity of the moiety thereby enhancing the reaction rate with nucleophilic salts containing the preferred cation. Use of the inventive leaving groups results in improved yields, decreased reaction times and improved product purity.