RING-CLOSURE REACTIONS INITIATED BY THE PEROXYDISULFATE ION OXIDATION OF DIPHENYL DISELENIDE

The oxidation of diphenyl diselenide with ammonium peroxydisulfate proceeded cleanly to afford phenylselenium cations and sulfate anions. This is a very simple and efficient method to produce phenylselenium cations in the absence of nucleophilic counterions. This reaction was employed to effect selenium-induced ring closure reactions starting from alkenes containing internal nucleophiles. Thus, unsaturated alcohols and amides, β-diketones and β-keto esters gave the products of phenylselenoetherification. The same process occurred with dienes and unsaturated ketones when the reaction was carried out in the presence of water or methanol, respectively. Unsaturated acids, esters, and imides afforded the phenylselenolactonization products. © 1990, American Chemical Society. All rights reserved.