Issue 7, 1978
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Bile pigment studies. Part 4. Some novel reactions of metalloporphyrins with thallium(III) and cerium(IV) salts. Ring cleavage of meso-tetraphenylporphyrin

Brian Evans,   Kevin M. Smith  and  José A. S. Cavaleiro  

Abstract

Treatment of zinc(II)meso-tetraphenylporphyrin (5) with thallium(III) trifluoroacetate or nitrate, or cerium(IV) ammonium nitrate gives a mixture of the 5,15-dihydroxy-5,10,15,20-tetraphenylporphodimethenes (7), the 5-hydroxy-15-methoxy-derivatives (8), and the ring-opened bilinone (10) after acidic demetallation. An extra product when thallium(III) trifluoroacetate is employed is the trifluoroacetyl derivative (12) or (13). When thallium(III) nitrate or cerium(IV) ammonium nitrate are used, the β-nitro-meso-tetraphenylporphyrin (14) is also isolated. Nitration of zinc(II) octa-alkylporphyrins with these two salts is shown to be a general reaction which can be controlled to give mono- or di-nitration at the meso-positions. Mechanistic implications of the ring-cleavage and nitration reactions are discussed.

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Article information

DOI
https://doi.org/10.1039/P19780000768
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1978, 768-773

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Bile pigment studies. Part 4. Some novel reactions of metalloporphyrins with thallium(III) and cerium(IV) salts. Ring cleavage of meso-tetraphenylporphyrin

B. Evans, K. M. Smith and J. A. S. Cavaleiro, J. Chem. Soc., Perkin Trans. 1, 1978, 768 DOI: 10.1039/P19780000768

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