Dv. Yashunsky et al., SYNTHESIS OF MESO-MONOSUBSTITUTED ETHANE-ETHYLENEBIS(PORPHYRINS) AND TRANS-ETHYLENEBIS(PORPHYRINS), Tetrahedron letters, 36(46), 1995, pp. 8485-8488
Vilsmeier reaction of mono-Ni 1,2-ethanebis(octaethylporphyrin) favour
ed 10-substitution. Functional group interconversions led to pure 10-d
imethylaminomethyl, -azomethine, -methoxymethyl, and -formyl derivativ
es. Demetallation gave a range of labile 10-substituted free base dime
rs. Oxidation of the mono-Ni compounds in AcOH gave the corresponding
trans-ethylene mono-Ni derivatives, while the free bases were all conv
erted to 10'-formyl-1,2-ethylenebis(octaethylporphyrin) under the same
conditions.