SNAr reactions of β-substituted porphyrins and the synthesis of meso substituted tetrabenzoporphyrins |
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Authors: | Mathias O Senge Ines Bischoff |
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Institution: | Institut für Chemie, Universität Potsdam, Karl-Liebknecht-Str. 24-25, D-14476 Golm, Germany |
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Abstract: | Reaction of 2,3,7,8,12,13,17,18-octaethylporphyrin with LiR reagents containing functional groups readily yields meso substituted derivatives suitable for further transformations with residues such as -p-C6H5Br, -p-C6H5-CCH, -p-C6H5-NH2 or -(CH2)3-CHCH2. Similar reactions of tetrabenzoporphyrin with alkyllithium reagents afforded the first entry into meso mono- and dialkylsubstituted tetrabenzoporphyrins while reaction of bicyclo2.2.2]oct-type masked isoindole precursors with LiR followed by in situ retro-Diels-Alder reaction also afforded the 5-phenyl and 5,10-diphenyltetrabenzoporphyrins in high purity. |
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Keywords: | Nucleophilic aromatic substitution Tetrabenzoporphyrins C-C coupling reactions Organolithium reagents Tetrapyrroles |
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