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From 21,23-Dioxaporphyrin to a 3-Pyranone Dioxacorrole Skeleton: The Achmatowicz Rearrangement in the Porphyrin Frame


  • Financial support from the Ministry of Science ang Higher Education (Grant N N204 021939 is kindly acknowledged. DFT calculations were carried out it the Poznań Supercomputer Centre.


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Be independent: Under basic conditions a furan ring entrapped in an aromatic macrocycle readily recovered the properties characteristic for a free molecule and assimilated a water molecule forming the Achmatowicz rearrangement product with a 3-pyranone subunit built in. Coordination of palladium(II) created a complex stabilizing the second tautomer with two sp3 carbon atoms (oxygen red, water green, palladium purple, and the aryl group blue).