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Paper | Regular issue | Vol 65, No. 10, 2005, pp.2339-2346
Published online, 9th August, 2005
DOI: 10.3987/COM-05-10467
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


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.