Micellar catalysis of the deamination of O-alkylhydroxylamines

Abstract

The bromide and thiocyanate ion-catalysed deamination of long-chain O-alkylhydroxylamines show normal reactivities at low substrate concentrations. There is a rapid increase in reactivity at the critical micelle concentration, the bromide-catalysed reaction showing a rather greater increase than the thiocyanate-catalysed reaction. The reactivity of the micelle increased with increased chain length. The origin of the micellar catalysis is discussed, and is ascribed to the association of catalytic anions at or close to the surface of the cationic micelle, in the immediate vicinity of the substrate amine groups.