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

Autor: Foglia, T., Haeberer, E., Maerker, G.
Zdroj: Journal of the American Oil Chemists' Society (JAOCS); Feb1970, 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 β-bromosulfonamides. The reaction has been applied to pairs of cis-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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index