Addition of N,N-dibromosulfonamides to internal olefins: Synthesis of N-sulfonylaziridines

Autor: Foglia, T. A., Haeberer, E. T., Maerker, G.
Zdroj: Journal of the American Oil Chemists' Society; February 1970, Vol. 47 Issue: 2 p27-32, 6p
Abstrakt: The addition of N,N-dibromobenzenesulfonamide (NNDBS) to internal acyclic olefins has been investigated. The major products formed were shown to be ß-bromosulfonamides. The reaction has been applied to pairs ofcis-transolefins and has been found to proceed in a stereoselective fashion. To account for this observed selectivity an ionic mechanism has been proposed. The ß-bromosulfonamides prepared have been cyclized with base to N-sulfonylaziridines. The configurations of the latter have been shown to be the same as those of the starting olefins.
Databáze: Supplemental Index