Summary
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1.
A study was made of the oxidation of 4-ethynyldecahydro-L,2-dimethyl-4-quinolinol and two isomeric 4-ethyldecahydro-1,2-dimethyl-4-quinolinols with hydrogen peroxide and with peroxyacetic acid.
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2.
With the aid of thin-layer chromatography on alumina and the crystallization of picrates it was shown that in the oxidation of each of these amino alcohols two isomeric (cis and trans) N-oxides are formed.
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3.
It was found for the first time that in the thin-layer chromatography of the picrates of the isomeric N-oxides on alumina the picrates break down into their components. Because of this it is possible to use the individual picrates of the isomeric N-oxides as reference compounds for N-oxides in the chromatography of mixtures of the latter. This method can probably be extended to other types of molecular compounds.
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Literature cited
A. A. Akhrem, L. I. Ukhova, and N. F. Uskova, Izv. AN SSSR. Otd. khim. n. 2 (1962).
H. Mills et al., J. Chem. Soc. 2613 (1927); see also I. Meisenheimer, et al., Liebigs Ann. Chem.449, 191 (1926).
I. N. Nazarov, L. I. Ukhova, and V. A. Rudenko, Izv. AN SSSR. Otd. khim. n. 730 (1953).
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Akhrem, A.A., Ukhova, L.I. & Sakovich, N.F. Synthesis and stereoisomerism of N-oxides of the decahydroquinoline series. Russ Chem Bull 12, 758–762 (1963). https://doi.org/10.1007/BF01134720
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DOI: https://doi.org/10.1007/BF01134720