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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The chemistry of pyrrolic compounds. XX. Bilenes-b as intermediates in the synthesis of porphyrins related to protoporphyrin IX. meso-Pyrrolylporphyrins

PS Clezy, AJ Liepa and NW Webb

Australian Journal of Chemistry 25(9) 1991 - 2001
Published: 1972

Abstract

α-Formyl-α'-methyldipyrrylmethanes have been shown to react with α,α'- dicarboxydipyrrylmethanes to give hexapyrrenes which cyclize with copper acetate in pyridine to yield meso-pyrrolylporphyrins. However, if an α,α'-dicarboxydipyrrylmethane is decarboxylated in N,N-dimethylformamide and the product converted into its monoimmonium salt (Vilsmeier-Haack intermediate) with benzoyl chloride this salt with an α-formyl-α'-methyldipyrrylrnethane affords a bilene-b which with copper acetate-pyridine gives a normal porphyrin. This latter procedure has been adapted to prepare tetrapyrroles of the protoporphyrin IX type. A synthesis of pemptoporphyrin dimethyl ester is reported.

https://doi.org/10.1071/CH9721991

© CSIRO 1972

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