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■ Synthesis of Porphyrin — Acetylene and Porphyrin-Diene Building Blocks for New Dyads Preparation

Stanislaw Ostrowski* and Agnieszka Mikus

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

Abstract

A new synthetic approach to porphyrin-acetylene and porphyrin-diene derivatives utilizing tetraphenylporphyrin (TPP) and two new reactions (vicarious nucleophilic substitution and metathesis) is described. 5-(4-Nitrophenyl)-10,15,20-triphenylporphyrin zinc complex reacts with ^-CHXY type carbanions, affording the nucleophilic substitution of hydrogen products containing CH₂SO₂Tol, CH₂SO₂Ph, CH₂SO₂NMe₂, and CH₂CN groups, respectively. The products obtained when alkylated with alkyl halides, bearing an acetylenic function in the terminal position, resulted in the formation of TPP-acetylene building blocks. These systems were subjected to cross-enyne metathesis reaction with ethylene (with the use of efficient ruthenium catalysts) to give the porphyrin-diene dyads - the excellent substrates for further transformations.