New methodology has been developed for the synthesis of so-called sapphyrins, pentapyrrolic 'expanded porphyrins'. An efficient approach involving acid-catalyzed condensation of 1,19-diunsubstituted a,c-biladienes and 3,4-dialkylpyrrole-2-carbaldehydes eliminates the preparation of bipyrrolic intermediates and allows the synthesis of sapphyrins with an unsymmetrical array of peripheral substituents. The β-substitution pattern of 2,3,13,17-tetraethyl-7,8,12,18,22,23-hexamethylsapphyrin has been unambiguously confirmed by single crystal X-ray crystallography. 1H NMR spectra of the dication salts of sapphyrins are strongly dependent upon the counterions, and the pattern of resonances observed in solution is related to the stacking interactions between the macrocycles.

Paolesse, R., Licoccia, S., Spagnoli, M., Boschi, T., Khoury, R., & Smith, K. (1997). A novel synthetic route to sapphyrins. JOURNAL OF ORGANIC CHEMISTRY, 62(15), 5133-5137 [10.1021/jo9704117].

A novel synthetic route to sapphyrins

PAOLESSE, ROBERTO;LICOCCIA, SILVIA;
1997

Abstract

New methodology has been developed for the synthesis of so-called sapphyrins, pentapyrrolic 'expanded porphyrins'. An efficient approach involving acid-catalyzed condensation of 1,19-diunsubstituted a,c-biladienes and 3,4-dialkylpyrrole-2-carbaldehydes eliminates the preparation of bipyrrolic intermediates and allows the synthesis of sapphyrins with an unsymmetrical array of peripheral substituents. The β-substitution pattern of 2,3,13,17-tetraethyl-7,8,12,18,22,23-hexamethylsapphyrin has been unambiguously confirmed by single crystal X-ray crystallography. 1H NMR spectra of the dication salts of sapphyrins are strongly dependent upon the counterions, and the pattern of resonances observed in solution is related to the stacking interactions between the macrocycles.
Pubblicato
Rilevanza internazionale
Articolo
Sì, ma tipo non specificato
Settore CHIM/07 - Fondamenti Chimici delle Tecnologie
English
Con Impact Factor ISI
PENTAPYRROLIC EXPANDED PORPHYRIN
Paolesse, R., Licoccia, S., Spagnoli, M., Boschi, T., Khoury, R., & Smith, K. (1997). A novel synthetic route to sapphyrins. JOURNAL OF ORGANIC CHEMISTRY, 62(15), 5133-5137 [10.1021/jo9704117].
Paolesse, R; Licoccia, S; Spagnoli, M; Boschi, T; Khoury, Rg; Smith, Km
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2108/53583
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