Design of New Organoselenium Reagents and Their Utilization in Organic Synthesis

Abstract

The results of the search for new organoselenium reagents and their utilization in organic synthesis are described herein. They include 1) phenylselenenyl chloride in acetonitrile/water (hydroxyselenation of olefins), 2) phenylselenenyl chloride/trifluoromethanesulphonic acid/water in acetonitrile (amidoselenation of olefins), 3) phenylselenenyl chloride/mercury (II) thiocyanate [selective synthesis of β- (phenylseleno) alkyl isothiocyanates], 4) phenylselenenyl bromide (intramolecular amidoselenation of N-alkenyl amides), 5) phenylselenenyl iodide (carbon-carbon bond formation in diolefins), 6) 2-pyridylselenenyl bromide (2-pyridylseleno group is a better leaving group than phenylseleno group in selenoxide elimination), 7) phenyl selenocyanate/copper or nickel halide/alcohol (oxyselenation of olefins), and 8) potassium selenocyanate/copper (II) halide (selenium-containing heterocycles from diolefins) and related reactions.