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Issue 0, 1972
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Sulphur extrusion reactions applied to the synthesis of corroles and related systems

Abstract

The preparation of 21,24-dioxacorroles by condensation of dipyrromethane-5,5′-dicarboxylic acids with 5,5′-diformyl-2,2′-bifuryl or bis-(5-formyl-2-furyl) sulphide is described. It is suggested that the latter reaction involves a non-aromatic meso-thia-macrocyclic intermediate which loses sulphur by a disrotatory cyclisation to a thiiran intermediate followed by cheletropic loss of sulphur. Some evidence for this proposal is provided by the preparation of meso-thiaphlorins and a study of their thermolyses to give corroles. Further examples of sulphur extrusion from a meso-dithiaphlorin, to give a meso-thiacorrole, are given and rate enhancements, in the sulphur extrusion process, which are observed in metal complexes are discussed. Some electrophilic deuteriation studies on the 21,24-dioxa-corroles are reported.

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Article type: Paper
DOI: 10.1039/P19720001124
Citation: J. Chem. Soc., Perkin Trans. 1, 1972,0, 1124-1135

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    Sulphur extrusion reactions applied to the synthesis of corroles and related systems

    M. J. Broadhurst, R. Grigg and A. W. Johnson, J. Chem. Soc., Perkin Trans. 1, 1972, 0, 1124
    DOI: 10.1039/P19720001124

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