Über die katalytische Dehydrierung cyclischer Basen, III. Mitteil.: Das Verhalten der stereoisomeren Dekahydro‐chinoline bei der Dehydrogenisations‐Katalyse

Ehrenstein, Maximilian; Bunge, Wilhelm

doi:10.1002/cber.19340671014

Cited by 15 publications

(5 citation statements)

References 11 publications

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“…proceeds more rapidly than that of the trans isomer (206). Similar behavior has been reported for the decahydroquinolines and the decalins on palladium (80).…”

Section: H2 H H2 Hsupporting

confidence: 77%

Sterochemistry and Heterogeneous Catalysis

Burwell¹

1957

Chem. Rev.

105

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“…proceeds more rapidly than that of the trans isomer (206). Similar behavior has been reported for the decahydroquinolines and the decalins on palladium (80).…”

Section: H2 H H2 Hsupporting

confidence: 77%

Sterochemistry and Heterogeneous Catalysis

Burwell¹

1957

Chem. Rev.

105

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“…analysis, JH NMR (see below), and 13G NMR7 spectral study. In the tricyclic series, 1,2,3,4,5,6,7,8-octahydroacri-dine1 (11) was reduced in high yield to trans-syn-transperhydroacridine (12, Scheme II).8 The stereoisomeric mixture of 5,6,6a,7,8,9,10,10a-octahydrobenzo[/z]quinolines (13) obtained by catalytic hydrogenation of the aromatic precursor1 was reduced to a mixture of three perhydrobenzo[/i]quinolines (14)(15)(16) in which the juncture of the piperidine to the adjacent cyclohexane ring was trans and the decalinoid ring fusion displayed the two possible cis junctures and one of the possible trans junctures (Scheme II).8…”

Section: Scheme Imentioning

confidence: 99%

Selective hydrogenation of quinoline and its homologs, isoquinoline, and phenyl-substituted pyridines in the benzene ring

Vierhapper¹,

Eliel²

1975

J. Org. Chem.

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Hydrogenation of quinoline, its 2-, 3-, 6-, and 8-methyl and 2-isopropyl homologs, isoquinoline, acridine, benzo[h]quinoline, 2-phenylpyridine, 4-phenylpyridine, and 4-(3-phenylpropyl)pyridine over platinum oxide (and, in some instances, palladium or rhodium on charcoal) in strong acid (12 N HC1,12 N H2SO4, CF3COOH) leads to selective hydrogenation of the benzene ring. The fastest procedure is one employing PtOs in trifluoroacetic acid.

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“…Dehydrogenation of the isomers of 2-n-butyl-S-methylpiperidine. The procedure and apparatus adapted from those described by Ehrenstein and Bunge (14) for the dehydrogenation of decahydroquinoline were used for the 2-n-butyl-3-methylpiperidines A and B. The dehydrogenation tube was charged with 1.0 g. of palladized asbestos.…”

Section: Stereoisomers Of 2-n-butyl-3-mbthylpiperidinementioning

confidence: 99%

“…The decision as to which is the cfs-form (IX, only one enantiomorph is shown) and which the trans-(X) was reached by dehydrogenation studies. Ehrenstein and Bunge (14) found that cfs-decahydroquinoline is more readily dehydrogenated than ¿raws-decahydroquinoline. Similarly, Witkop (15) found that cisdecahydroisoquinoline is more readily dehydrogenated with palladium than írans-decahydroisoquinoline, and concluded that the difference may be due to the relatively easier approach of the cis compound to the catalyst surface for removal of pairs of adjacent hydrogen atoms.…”

mentioning

confidence: 99%