On Selective Functionalization of meso-Tetraphenylporphyrin Derivatives by Vicarious Nucleophilic Substitution of Hydrogen

Abstract

The studies on selective derivatization of meso-tetraphenylporphyrin (TPP) using nitration and Vicarious Nucleophilic Substitution of Hydrogen (VNS) are reported.TPP, its metal complexes and N,N-dimethyl substituted derivatives do not enter the VNS reaction.On the other hand, meso-substituted TPP results in the mono-nitration of one phenyl ring and the intermediate obtained, after simple transformation to its metal complex, reacts with carbanions bearing leaving groups at the carbanionic center, according to VNS scheme.This gives new opportunities for the peripheral functionalization of porphyrins.In this work the copper and zinc complexes were investigated.