Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 9. New reagents for amination of the ethylenic linkage

Abstract

Treatment of disulphides, especially diphenyl disulphide, with chloramine-T affords a series of reagents which react with olefins to give adducts. These reactions are electrophilic in nature, with PhS⁺ initiating the reaction and a complex nitrogen anion terminating the process. Similar, but less extensive, experimentation has been carried out with diselenides, especially diphenyl diselenide. These new reagents provide a novel procedure for the amination of the ethylenic linkage.