Metal template reactions. III. Synthesis of macrocyclic quadridentate nickel(II) complexes from a suitable diamino dialdehyde

Abstract

N,N-Bis(2-formyl-4-nitrophenyl)ethyleneiamine has been synthesized by a sequence of reactions involving the alkylation of ethylenediamine with the ethylene-dioxy derivative of 6-chloro-3-nitrobenzaldehyde and hydrolysis of the resulting product. Neutral macrocyclic nickel(11) complexes have been prepared by the reaction of this diaminodialdehyde with ethylenediamine, o-phenylenediamine, and 1,8-diaminonaphthalene respectively, in the presence of nickel(11) acetate tetrahydrate. Macrocyclic complexes could not be obtained by the reaction of the neutral nickel(11) complex of N,N'-bis(2-formyl-4-nitrophenyl)ethylenediamine with ethylene-diamine. Other experiments towards the synthesis of a diamino dialdehyde suitable for metal template reactions are described.