Low-Pressure Hydrogenation of Alkoxyanilines with Noble Metal Catalysts

Freifelder, Morris; Ng, Yew Hay; Helgren, Preston F.

doi:10.1021/jo01018a524

Cited by 16 publications

(3 citation statements)

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“…A. Perjéssy, P. Hrnciar, and R. Sokolová, ibid., in press (10). A. Perjéssy, P. Hrnóiar, R. Frimm, and L. FiSera, Tetrahedron, 28,3781 (1972).those for a series of írans-l-phenyl-3-arylpropenones (III) (chalcones) reported earlier.1,2 Results and Discussion Carbonyl Stretching Frequencies.…”

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confidence: 85%

“…When comparing the data from Tables I and II with that for chalcones III2,3 (see Table III), we found that the insertion of the furan or thiophene intervening group in the chalcone system produces a significant decrease in both the ivcis and ivtrans frequency similar to the other previously described cases. [7][8][9][10] In passing from CCI4 to CHCI3 we observe a decrease of 6.0-6.5 cm-1 in the «8 frequency of compounds in both series I and II. However, in the case (12) S. V. Tsukerman, V. M, Nikitchenko, J. S. Rozum, and V. F. Lavrushin, Khim.…”

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confidence: 95%

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Carbonyl stretching frequencies and transmission of electronic effects in 1-phenyl-3-(5-aryl-2-furyl)propenones and 1-phenyl-3-(5-aryl-2-thienyl)propenones

Perjéssy¹,

Boykin²,

Fisera³

et al. 1973

J. Org. Chem.

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The s-cis and s-trans carbonyl stretching frequencies of a series of fraras-l-phenyl-3-(5-aryl-2-furyl )propenones (I) and ¿raras-l-phenyl-3-(5-aryl-2-thienyl)propenones (II) have been measured in carbon tetrachloride and chloroform solutions. Statistically significant linear free-energy relationships were obtained between y(C=0) and + constants; poorer correlations using values were obtained in all cases. The data were also treated using the Swain-Lupton F and R constants, and poorer correlations than noted with + were obtained. The influence of the conformation on the transmission of electronic effects is discussed and compared with that in analogous systems. The parameters of the linear free-energy relationships for series I and II were compared with those for a series of ¿raras-l-phenyl-3-arylpropenones (III). Using the slopes of y(C=0) vs. + correlations in series I-III the transmissive factors for the furan and thiophene rings were calculated and related to data published earlier. The determined order of transmission for the intervening groups was furan > thiophene > benzene.

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confidence: 85%

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confidence: 95%

Carbonyl stretching frequencies and transmission of electronic effects in 1-phenyl-3-(5-aryl-2-furyl)propenones and 1-phenyl-3-(5-aryl-2-thienyl)propenones

Perjéssy¹,

Boykin²,

Fisera³

et al. 1973

J. Org. Chem.

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“…cis-and trans-3-Aminocyclohexanol. 3-Acetamidophenol (20g) in methanol (75ml) was hydrogenated for lOOh at a pressure of 351b/in2 (241kN-mM2) at room temperature by using a 5 % rhodium-alumina catalyst (Freifelder et al, 1965). Analysis by g.l.c.…”

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confidence: 99%

The metabolites of cyclohexylamine in man and certain animals

Renwick

Williams

1972

Biochemical Journal

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1. [1-(14)C]Cyclohexylamine hydrochloride was synthesized and given orally or intraperitoneally to rats, rabbits and guinea pigs (dose 50-500mg/kg) and orally to humans (dose 25 or 200mg/person). The (14)C is excreted mainly in the urine, most of the excretion occurring in the first day after dosing. Only small amounts (1-7%) are found in the faeces. 2. In the rat, guinea pig and man, the amine is largely excreted unchanged, only 4-5% of the dose being metabolized in 24h in the rat and guinea pig and 1-2% in man. In the rabbit about two-thirds of the dose is excreted unchanged and about 30% is metabolized. 3. In the rat, five minor metabolites were found, namely cyclohexanol (0.05%), trans-3- (2.2%), cis-4- (1.7%), trans-4- (0.5%) and cis-3-aminocyclohexanol (0.1% of the dose in 24h). 4. In the rabbit, eight metabolites were identified, namely cyclohexanol (9.3%), trans-cyclohexane-1,2-diol (4.7%), cyclohexanone (0.2%), cyclohexylhydroxylamine (0.2%) and trans-3- (11.3%), cis-3- (0.6%), trans-4- (0.4%) and cis-4-aminocyclohexanol (0.2%). 5. In the guinea pig, six minor metabolites were found, namely cyclohexanol (0.5%), trans-cyclohexane-1,2-diol (2.5%) and trans-3- (1.2%), cis-3- (0.2%), trans-4- (0.2%) and cis-4-aminocyclohexanol (0.2%). 6. In man only two metabolites were definitely identified, namely cyclohexanol (0.2%) and trans-cyclohexane-1,2-diol (1.4% of the dose), but man had been given a smaller dose (3mg/kg) than the other species (50mg/kg). 7. The hydroxylated metabolites of cyclohexylamine were excreted in the urine in both free and conjugated forms. 8. Although cyclohexylamine is metabolized to only a minor extent, in rats the metabolism was mainly through hydroxylation of the cyclohexane ring, in man by deamination and in guinea pigs and rabbits by ring hydroxylation and deamination.

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By Rhodium Catalysts

Gras¹

1993

Inorganic Reactions and Methods

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Low-Pressure Hydrogenation of Alkoxyanilines with Noble Metal Catalysts

Cited by 16 publications

References 1 publication

Carbonyl stretching frequencies and transmission of electronic effects in 1-phenyl-3-(5-aryl-2-furyl)propenones and 1-phenyl-3-(5-aryl-2-thienyl)propenones

Carbonyl stretching frequencies and transmission of electronic effects in 1-phenyl-3-(5-aryl-2-furyl)propenones and 1-phenyl-3-(5-aryl-2-thienyl)propenones

The metabolites of cyclohexylamine in man and certain animals

By Rhodium Catalysts

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