New route to macrocycles : synthesis of macrocycle via McMurry coupling

Abstract

Named after its discoverer, John McMurry, McMurry coupling involves reductive dimerization of carbonyl compounds to yield olefins on treatment with low-valent titanium reagent. In this project, this mechanism had been adopted in order to synthesize an interesting macrocycle molecule. A TiCl4/Zn reagent system was employed. Isophthaloyl chloride had first undergone Friedel-Crafts acylation with octyl benzene. The diketone formed from acylation was the precursor for the McMurry coupling reaction.