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Synthesis and stereoisomerism of N-oxides of the decahydroquinoline series

IV. Establishment of the configuration of epimeric N-oxides of 4-substituted 1,2-dimethyldecahydro-4-quinolols by PMR spectroscopy

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Abstract

The orientation of the substituents attached to the nitrogen atom in epimeric N-oxides of 1,2-dimethyl-4-ethynyl (vinylethynyl, vinyl, acetyl) decahydro-4-quinolols was established by means of PMR spectroscopy with the aid of the dependence of the chemical shifts of the 3-Ha and 3-He protons on the orientation of the N→O bond and the effect of the diamagnetic anisotropy of the C-C and C-H bonds of the rings. It was found that the equatorial methyl group attached to the nitrogen atom resonates at weaker field than the axial methyl group. The quantitative ratio of the epimeric N-oxides in the mixtures was determined.

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Literature cited

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, Academy of Sciences of the Belorussian SSR, Minsk

    A. A. Akhrem, V. M. Gorul'ko, L. I. Ukhova, N. F. Marchenko & A. P. Marochkin

Authors
  1. A. A. Akhrem
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  2. V. M. Gorul'ko
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  3. L. I. Ukhova
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  4. N. F. Marchenko
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  5. A. P. Marochkin
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Additional information

See [1] for communication III.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1372–1377, October, 1976.

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Akhrem, A.A., Gorul'ko, V.M., Ukhova, L.I. et al. Synthesis and stereoisomerism of N-oxides of the decahydroquinoline series. Chem Heterocycl Compd 12, 1136–1140 (1976). https://doi.org/10.1007/BF00945600

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  • DOI: https://doi.org/10.1007/BF00945600

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