Investigation of the Scope of Heterogeneous and Homogeneous Procedures for Preparing Magnesium Chelates of Porphyrins, Hydroporphyrins, and Phthalocyanines.

A simple method has been developed for metalation of porphyrinic compounds under homogeneous conditions at room temperature using a stable ethereal solution of MgI(2) and N,N-diisopropylethylamine. A previously developed heterogeneous procedure employs a mixture of a magnesium halide and a nonnucleophilic amine in a noncoordinating solvent at room temperature. The scope of the heterogeneous and homogeneous magnesium insertion procedures has been investigated across a family of 19 porphyrinic compounds, including synthetic porphyrins, synthetic or naturally occurring chlorins, and organic-soluble phthalocyanines.