Abstract
A new macrocyclic hexaaza binucleating Schiff base ligand 3,7,11,19,23,27-hexaazatricyclo[27.3.1.1 13,17]tetratriaconta-1(32),2,11,13(14),15,17(34),18,27,29(33),30-decaene (MX 2DIPN 2 or 1) has been prepared in good yield by direct condensation of m-phthalaldehyde and 3,3′-iminobis(propylamine). MX 2DIPN 2 forms a dinuclear Cu(I) complex that reacts with molecular oxygen to form [(MX 2DIPN 2)Cu 2(O 2)] 2+. This oxygen complex does not undergo intramolecular oxygen insertion into the phenyl ring in sharp contrast with its macrocyclic analog [(MX 2DIEN 2)Cu 2(O 2)] 2+ (MX 2DIEN 2 is the macrocyclic ligand formed by the condensation of m-phthalaldehyde and diethylenetriamine), the result of the enlargement of the macrocyclic cavity. It has been shown that [(MX 2DIPN 2)Cu 2(O 2)] 2+ is an efficient and selective catalyst for the oxidation of 3,5-di- t-butylcatechol to 3,5-di- t-butyl-1,2-benzoquinone in the presence of 1 atm O 2. Furthermore, the measured initial rate constants reveal that it reacts much faster than any of the related macrocyclic systems reported to date.
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