Abstract:Several approaches to the synthesis of porphyrins bearing fused six- membered ring systems were explored with the aim of obtaining the petroporphyrin (4a). This was ultimately achieved by an intramolecular cyclization of a porphyrin with a propanoyl chloride side chain in the presence of stannic chloride. Methylation of the intermediate ketone with CH3Li and reduction of the resultant alcohol with NaBH3CN/Znl2 furnished (4a).
“…These molecules have been most popular for their use in the synthesis of porphyrins, − chlorins, , and tetrahydrocorrins. , The 1,19-dimethyl-derivatives, sometimes formed in situ, have also been used to synthesize metalloporphyrins by cyclization in the presence of metal ions. − From the earliest of these metal cyclization reactions it was discovered that bilene- b analogues form homoleptic metal complexes . This work was extended to investigate the metal-complex geometries of dipyrrins through a study upon bilene- b metal complexes such as compound 72 : it was shown that they displayed complexation behavior similar to that of 1,9-sterically hindered dipyrrins (Figure ). , 72 Structure of a zinc(II) bilene- b complex.…”
“…These molecules have been most popular for their use in the synthesis of porphyrins, − chlorins, , and tetrahydrocorrins. , The 1,19-dimethyl-derivatives, sometimes formed in situ, have also been used to synthesize metalloporphyrins by cyclization in the presence of metal ions. − From the earliest of these metal cyclization reactions it was discovered that bilene- b analogues form homoleptic metal complexes . This work was extended to investigate the metal-complex geometries of dipyrrins through a study upon bilene- b metal complexes such as compound 72 : it was shown that they displayed complexation behavior similar to that of 1,9-sterically hindered dipyrrins (Figure ). , 72 Structure of a zinc(II) bilene- b complex.…”
ChemInform Abstract The title compound (V) is synthesized by a strategy involving formation of the porphyrin macrocycle (III), followed by cyclization of a propanoyl chloride side chain in the presence of SnCl4. The macrocycles fused with a six-membered ring system are of interest in connection with the question, if petroporphyrins found in petroleum and similar deposits in general have their origin in chlorophylls which were part of living systems of past geological ages (yields in g).
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