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From 21,23‐Dioxaporphyrin to a 3‐Pyranone Dioxacorrole Skeleton: The Achmatowicz Rearrangement in the Porphyrin Frame
Author(s) -
Pawlicki Miłosz,
Bykowski Dominik,
Szterenberg Ludmiła,
LatosGrażyński Lechosław
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201109038
Subject(s) - tautomer , porphyrin , palladium , molecule , chemistry , ring (chemistry) , furan , aryl , stereochemistry , photochemistry , medicinal chemistry , crystallography , organic chemistry , catalysis , alkyl
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 sp 3 carbon atoms (oxygen red, water green, palladium purple, and the aryl group blue).