Abstract
The synthesis, characterization, and examination of the monooxygenase activity of tetrapyrrolic macrocyclic complexes with an accordion porphyrin-like ligand framework are described. Cyanovinyl protection techniques were used to obtain a diformyl dipyrromethane, which was condensed with 1,3-diaminopropane in the presence of metal acetate template to achieve manganese(II), nickel(II), and copper(II) complexes. The macrocycle was found to be in the dipyrromethene form for both the manganese(II) and copper(II) complexes, and in the dipyrromethane form for the nickel(II) complex. The crystal structure of the acetate salt of the manganese(II) complex was obtained. The manganese(II) complex was found to catalyze the epoxidation of cyclohexene, yielding primarily the epoxide (40%) with only minor side products, while the nickel(II) and copper(II) complexes showed little catalytic activity. A lack of stereoselectivity was observed in the epoxidation of cis- and trans-stilbene by the manganese(II) complex, which yielded only trans-epoxide in the reaction with trans-stilbene, but both cis and trans products in the reaction with cis-stilbene.
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