Arylsulfonate esters in solid phase organic synthesis. I. Cleavage with amines, thiolate, and imidazole

Article abstract of DOI:10.1016/S0040-4039(97)10719-5

The arylsulfonate ester functionality connecting an alkyl chain to a polystyrene resin is cleaved with neat volatile primary or secondary amines to give secondary or tertiary amines, respectively, in high yields and purity. Non-volatile secondary amines, thiols, and imidazole also cleave the alkyl chain efficiently to afford the expected products which can be readily purified by an ion-exchange resin work-up method.