New Approach towards meso-Substituted trans-A2B-Corroles from Alkyl Oxalyl Chlorides and Dipyrromethanes

Beata Koszarna; Roman Voloshchuk; Daniel T. Gryko

doi:10.1055/s-2007-965988

PAPER

New Approach towards meso-Substituted trans-A₂B-Corroles from Alkyl Oxalyl Chlorides and Dipyrromethanes

Beata Koszarna, Roman Voloshchuk, Daniel T. Gryko*
Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
Fax: +48(22)6326681; e-Mail: daniel@icho.edu.pl;

Abstract

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Abstract

A one-pot synthesis of trans-A₂B-corroles via the condensation of dipyrromethanes with alkyl oxalyl chlorides followed by the macrocyclization mediated by DDQ has been developed. After thorough examination of different substrates, only reactive acid chlorides have been found to be suitable for this transformation. It was proved that these conditions work well for dipyrromethanes possessing various electron-withdrawing or sterically hindered substituents. No porphyrins are formed under these conditions. The whole sequence implies the formation of a ketone followed by its reaction with the second molecule of dipyrromethane and oxidation of a bilene to the respective corrole. Under the present reaction conditions, the use of typical dipyrromethanes and aromatic/aliphatic acid chlorides did not lead to the formation of corroles.

Key words

aldehydes - corroles - macrocycles - oxidations - pyrroles

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References

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