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.
From 21,23-Dioxaporphyrin to a 3-Pyranone Dioxacorrole Skeleton: The Achmatowicz Rearrangement in the Porphyrin Frame†
Article first published online: 26 JAN 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 10, pages 2500–2504, March 5, 2012
How to Cite
Pawlicki, M., Bykowski, D., Szterenberg, L. and Latos-Grażyński, L. (2012), From 21,23-Dioxaporphyrin to a 3-Pyranone Dioxacorrole Skeleton: The Achmatowicz Rearrangement in the Porphyrin Frame. Angew. Chem. Int. Ed., 51: 2500–2504. doi: 10.1002/anie.201109038
- Issue published online: 1 MAR 2012
- Article first published online: 26 JAN 2012
- Manuscript Received: 21 DEC 2011
- Ministry of Science ang Higher Education. Grant Number: N204 021939
- Achmatowicz reaction;
- solid-supported reactions
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).