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Neue 21,22‐Dioxaporphyrin‐5(23 H )‐one, Sauerstoff‐Analoga der Oxophlorine
Author(s) -
Rusch Roland,
Gast Achim,
Breitmaier Eberhard
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1990199001212
Subject(s) - chemistry , dichloromethane , tautomer , annulene , acetic anhydride , medicinal chemistry , proton nmr , porphyrin , stereochemistry , organic chemistry , catalysis , solvent
New 21,22‐Dioxaporphyrin‐5(23 H )‐ones, Oxygen Analogues of Oxophlorins 12,13,17,18‐Tetraalkyl‐21,22‐dioxaporphyrin‐5(23 H )‐ones 10 (21,22‐dioxa‐5‐oxophlorins) have been synthesized by MacDonald cyclization from Bis(5‐formyl‐2‐furyl)methanone ( 4 ) and 3,3′,4,4′‐tetraalkyl‐2,2′‐dipyrrylmethanes 8 in dichloromethane with acetic anhydride. IR, UV and NMR spectroscopic data have been compared with those of 3,7,13,17‐tetraethyl‐2,8,12,18‐tetramethyl‐21 H ,23 H ‐porphyrin‐5(22 H )‐one ( 12 ) which has also been newly synthesized. NMR shifts did not provide evidence for the diaza[18]annulene tautomers 11 of the 21,22‐dioxaphlorin‐5‐ones 10 .