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Formation of I- and III-Type Porphyrins by the Polymerization of Pyrroles

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Abstract

IN a recent paper1 we discussed the alkylation of tri- and tetra-alkylpyrroles and referred to the 2 : 3 : 4-trialkylpyrroles which on alkylation could give either 2 : 3 : 4 : 5-tetra-alkylpyrroles or 2 : 2 : 3 : 4-tetra-alkyl-2(H)pyrroles (for example, I). The factors which decided the course of this reaction were delicately balanced, for whereas the methylation of the Grignard derivative of 2 : 3 : 4-trimethylpyrrole gave 2 : 3 : 4 : 5-tetramethylpyrrole almost exclusively, a similar methylation of 2 : 4-dimethyl-3-ethylpyrrole (cryptopyrrole) gave 3-ethyl-2 : 2 : 4-trimethyl-2(H)pyrrole (I) as the major product.

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References

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Authors and Affiliations

  1. Department of Chemistry, The University, Nottingham,

    E. BULLOCK, A. W. JOHNSON, E. MARKHAM & K. B. SHAW

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  1. E. BULLOCK
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  2. A. W. JOHNSON
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  3. E. MARKHAM
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  4. K. B. SHAW
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BULLOCK, E., JOHNSON, A., MARKHAM, E. et al. Formation of I- and III-Type Porphyrins by the Polymerization of Pyrroles. Nature 185, 607–609 (1960). https://doi.org/10.1038/185607a0

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