cheminform abstract: a novel synthetic route to sapphyrins

1997 pyrrole derivatives pyrrole derivatives R 0120 49 - 138 A Novel Synthetic Route to Sapphyrins. — The title compounds are increasing in interest notably due to their unusual chemical, physical, and spectroscopic characteristics. A novel synthetic approach is reported, which allows the preparation of sapphyrins such as (III) with an unsymmetrical distribution of the peripheral substituents by an acid-catalyzed condensation of 1,19- diunsubstituted a,c-biladienes and pyrrol-2-carbaldehydes. (III) is isolated as its dihydrochloride. Such substances were previously impossible to obtain using the classical MacDonald-type approach. The 1H NMR spectra of the dication salts of sapphyrins are strongly dependent upon the counterions. — (PAOLESSE, R.; LICOCCIA, S.; SPAGNOLI, M.; BOSCHI, T.; KHOURY, R. G.; SMITH, K. M.; J. Org. Chem. 62 (1997) 15, 5133-5137; Dip. Sci. Tecnol. Chim., Univ. Tor Vergata, I-00133 Roma, Italy; EN) 1

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Page 1: ChemInform Abstract: A Novel Synthetic Route to Sapphyrins

1997 pyrrole derivatives

pyrrole derivativesR 0120

49 - 138A Novel Synthetic Route to Sapphyrins. — The title compoundsare increasing in interest notably due to their unusual chemical, physical, andspectroscopic characteristics. A novel synthetic approach is reported, whichallows the preparation of sapphyrins such as (III) with an unsymmetricaldistribution of the peripheral substituents by an acid-catalyzed condensation of1,19- diunsubstituted a,c-biladienes and pyrrol-2-carbaldehydes. (III) is isolatedas its dihydrochloride. Such substances were previously impossible to obtainusing the classical MacDonald-type approach. The 1H NMR spectra of thedication salts of sapphyrins are strongly dependent upon the counterions. —(PAOLESSE, R.; LICOCCIA, S.; SPAGNOLI, M.; BOSCHI, T.; KHOURY, R.G.; SMITH, K. M.; J. Org. Chem. 62 (1997) 15, 5133-5137; Dip. Sci. Tecnol.Chim., Univ. Tor Vergata, I-00133 Roma, Italy; EN)

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