Tetraphenylbenziporphyrin--a ligand for organometallic chemistry.
6,11,16,21-Tetraphenylbenziporphyrin (TPBPH)H, an analogue of tetraphenylporphyrin with one of the pyrrole groups replaced by a benzene ring, is formed in good yield in the condensation of the appropriate precursor with pyrrole and benzaldehyde. (TPBPH)H gives organometallic complexes with palladium(II) and platinum(II), [(TPBP)PdII] and [(TPBP)PtII], in which the metal ion is bound in the macrocyclic cavity by three pyrrolic nitrogen atoms and a carbon atom of the benzene ring. In the reaction with silver(I) acetate benziporphyrin does not yield a stable complex but undergoes selective acetoxylation at the internal carbon atom. (TPBPH)H is reversibly reduced to 6-benziphlorin and reacts with a water or methanol molecule to give 6-hydroxy- or 6-methoxy-6-benziphlorin, respectively.
Stepień
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M
Department of Chemistry, University of Wrocław, Poland.
Latos-Grazyński
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L
D001547:Benzaldehydes / Q000737:chemistry; D018360:Crystallography, X-Ray; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D010984:Platinum / Q000737:chemistry; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry
D001547:Benzaldehydes; D008024:Ligands; D009942:Organometallic Compounds; D011166:Porphyrins; C409084:tetraphenylporphyrin; D010984:Platinum; D010165:Palladium; C032175:benzaldehyde