Polymer-Supported Acetylenic Sulfones

Significance

Acetylenic sulfones were anchored onto the Merrifield resin by an ester linker. Sulfonhydrazide 1 was converted into selenosulfonate 2, followed by free radical selenosulfonation of actylenes to give adducts 3a-c. Esterification of resin 4 with 3a-c afforded the desired products 5a-c, respectively. Desilylation of 5c gave the terminal acetylene 5d. Resins 5a,b,d were subjected to a variety of cyclization and cycloaddition reactions with chloroamines 6 and 7, cyclopentadiene 8, and nitrile N-oxide 9 to give the corresponding cycloadducts (17 examples, 34-100% yield).