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Paper | Regular issue | Vol 57, No. 9, 2002, pp.1615-1626
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9514
On Selective Functionalization of meso-Tetraphenylporphyrin Derivatives by Vicarious Nucleophilic Substitution of Hydrogen

Stanislaw Ostrowski,* Agnieszka Mikus, Young Key Shim, Jong-Cheol Lee, Eun-Young Seo, Kee-In Lee, and Marian Olejnik

*Institute of Chemistry, University of Podlasie, ul. 3-go Maja 54, 08-110 Siedlce, Poland

Abstract

The studies on selective derivatization of meso-tetraphenylpor-phyrin (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.