High-field NMR study of the tautomers resulting from the condensation of 2-methylindole and phenalenone in the presence of p-toluenesulphonic acid

As phenalene is an alternant hydrocarbon it is oxidized very easily to phenalenone, which condenses with various nitrogen nucleophiles in the presence of p‐toluenesulphonic acid. 2‐Methylindolylphenalene is obtained with 2‐ methylindole, together with other products. This product is a mixture of fiv...

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Veröffentlicht in:Magnetic resonance in chemistry 1992-08, Vol.30 (8), p.689-696
Hauptverfasser: Tort, F., Waegell, B., Zahra, J. P., Bernasconi, C., Germanaud, L., Bessibes, C., Bounoure, J.
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Sprache:eng
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Zusammenfassung:As phenalene is an alternant hydrocarbon it is oxidized very easily to phenalenone, which condenses with various nitrogen nucleophiles in the presence of p‐toluenesulphonic acid. 2‐Methylindolylphenalene is obtained with 2‐ methylindole, together with other products. This product is a mixture of five tautomers in equilibrium, and these were analysed by homo‐ and heteronuclear two‐dimensional high‐field NMR (500 MHz) spectroscopy.
ISSN:0749-1581
1097-458X
DOI:10.1002/mrc.1260300802