Faculté des sciences

Catalytic Hydrogenation of meso-Octamethylporphyrinogen (Calix[4]pyrrole)

Journot, Guillaume ; Letondor, Christophe ; Neier, Reinhard ; Stoeckli-Evans, Helen ; Savoia, Diego ; Gualandi, Andrea

In: Chemistry - A European Journal, 2010, vol. 16, no. 4, p. 4224-4230

Hydrogenation of meso-octamethylporphyrinogen (calix[4]pyrrole) with a number of heterogeneous catalysts under different experimental conditions has been investigated. GC-MS analyses of the reaction mixtures showed the formation of one to four products in low to moderate yields: three of them were diastereoisomers of the product derived from half-hydrogenation of the substrate, and displayed... Mehr

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    Summary
    Hydrogenation of meso-octamethylporphyrinogen (calix[4]pyrrole) with a number of heterogeneous catalysts under different experimental conditions has been investigated. GC-MS analyses of the reaction mixtures showed the formation of one to four products in low to moderate yields: three of them were diastereoisomers of the product derived from half-hydrogenation of the substrate, and displayed alternating pyrrolidine and pyrrole rings, while the fourth was the all-cis saturated product. An acidic medium was necessary to achieve hydrogenation. However, the use of too strongly acidic solvents or additives was detrimental to the stability of the substrate and/or the catalyst.