Abstract
Hydrogenation of 6- or 8-R-substituted quinaldines [R=H, CH3, CH(CH3)2, C(CH3)3, or CF3] over platinum in trifluoroacetic acid gave higher yields (∼90%) of 5,6,7,8-tetrahydroderivatives than hydrogenation of the corresponding quinolines. ThepKa-values of 20 quinolines and quinaldines were determined by measuring the half-neutralization potentials in acetic anhydride. More basic quinolines gave higher yields of 5,6,7,8-tetrahydroproduct; exceptions are 6- and 8-methylquinoline and 8-tert. butylquinoline. Explanations for these observations are suggested.
Zusammenfassung
Katalytische Hydrierung von 6- oder 8-R-substituierten Chinaldinen [R=H, CH3, CH(CH3)2, C(CH3)3 oder CF3] über Platin in Trifluoressigsäure ergab höhere Ausbeuten (∼90%) an 5,6,7,8-Tetrahydroderivaten als die Hydrierung der entsprechenden Chinoline. DiepKa-Werte von 20 Chinolinen und Chinaldinen wurden durch die Messung der Halbneutralisationspotentiale in Essigsäureanhydrid bestimmt. Stärker basische Chinoline gaben höhere Ausbeuten an 5,6,7,8-Tetrahydroprodukten. Ausnahmen sind 6- und 8-Methyl-und 8-tert. Butylchinolin. Ein Versuch zur Erklärung der Beobachtungen wird unternommen.
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Dedicated to Prof. Dr.K. Schlögl on the occasion of his 60th birthday.
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Hönel, M., Vierhapper, F.W. Selectivity of hydrogenations. Part 4 6- and 8-substituted quinaldines yield of tetrahydroderivatives and basicities of quinolines. Monatsh Chem 115, 1219–1228 (1984). https://doi.org/10.1007/BF00809353
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DOI: https://doi.org/10.1007/BF00809353