Reactions of polyhalomethanes with olefins catalyzed by copper complexes with aromatic amino alcohols

Abstract

Copper complexes with amino alcohols structurally similar to ephedrin (1-phenyl-3-(N-methylamino)propan-1-ol and 1-phenyl-2-(N-methylamino)ethanol) are catalytically very active in the free-radical addition of CCl4 and CBr4 to linear alk-1-enes. These amino alcohols themselves are initiators of radical addition reactions, and, in the reaction with CBr4, they are more active than the metal complexes. In the presence of the amino alcohols, as distinct from classical radical initiators, the reaction is highly selective and affords an addition product. An analysis of kinetic equations and the data obtained for the reaction involving CHCl3 suggest that the amino alcohols and the corresponding metal complexes are involved in different ways in the addition of CCl4 and CBr4 to linear alk-1-enes.