T. Foglia, E. T. Haeberer, G. Maerker
Feb 1, 1970
Citations
1
Influential Citations
7
Citations
Journal
Journal of the American Oil Chemists Society
Abstract
The addition of N,N-dibromobenzenesulfonamide (NNDBS) to internal acyclic olefins has been investigated. The major products formed were shown to be β-bromosulfonamides. The reaction has been applied to pairs ofcis-trans olefins and has been found to proceed in a stereoselective fashion. To account for this observed selectivity an ionic mechanism has been proposed. The β-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.