Selenium Radical Ions in Organic Synthesis

Abstract

Selenium radical anions are suggested to be the reactive intermediates in the reductive cleavage of aryl alkyl, vinyl alkyl or vinyl acyl selenides; the aryl and vinyl selenolate anions thus obtained have been used to synthetize several types of selenium containing compounds. Radical cations are suggested to intervene in the oxydeselenenylation of aryl alkyl selenides promoted by oxidizing agents in hydroxylated solvents. This process has been used to effect the conversions of alkenes and vinyl bromides into dialkoxyalkanes and α-alkoxy acetals, and of alkynes and methyl ketones into α-keto ketals and α-keto acetals which occur by treatment with persulphate ions and catalytic amounts of diphenyl diselenide.