Conclusions
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1.
The rate of hydrogenation of cresol, alkylanillnes, aminophenols, and alkoxyanilines on Ru-Al2O3 in aqueous medium is 1.5–5 times as high as in ethanol. The reaction rate decreases in the series p- > m- > o-, as well as with increasing size of the alkyl substituent (C1-C6) and the introduction of alkyl and acetyl substituents into the amino group.
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2.
Alkylanilines, aminophenols, phenylenediamines, and N-acetyltoluidines are hydrogenated with high selectivity; the yield of the basic product reaches 82–98%.
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3.
In the case of hydrogenation of disubstituted benzenes under the investigated conditions, the composition of the stereoisomers formed is not determined by their thermodynamic stability — in all cases the cis-isomer predominates.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 976–982, May 1976.
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Freidlin, L.K., Litvin, E.F., Yakubënok, V.V. et al. Investigation of the catalytic hydrogenation of disturbed benzenes and the configurational isomerization of the corresponding cyclohexanes. Russ Chem Bull 25, 952–958 (1976). https://doi.org/10.1007/BF00921971
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DOI: https://doi.org/10.1007/BF00921971