THE USE OF SELENIUM CONTAINING INTERMEDIATES TO MEDIATE OR CATALYZE NEW ORGANIC-REACTIONS

Ammonium peroxydisulfate reacts with diphenyl diselenide to produce phenylselenenyl sulfate which acts as a strong selenenylating agent of unsaturated compounds. The same oxidizing agent also reacts with alkyl phenyl selenides giving rise to substitution or elimination products and regenerating the selenenylating species. A multi step one pot procedure, which requires only catalytic amounts of diphenyl diselenide, is presented and illustrated by several new or traditional conversions of functional groups. Iodobenzene diacetate can also be employed to oxidize PhSeSePh and to effect the selenenylation of unsaturated compounds. When sodium azide is employed the fastest process becomes the oxidation of the azido anions to azido radicals. The azido phenylselenenylation products are thus formed as the result of a radical addition. These versatile compounds have been employed to effect the syntheses of pyridine derivatives and of lactams.