Advertisement

Chemistry of Heterocyclic Compounds

, Volume 4, Issue 4, pp 444–447 | Cite as

Six-membered heterocycles

I. The stereoisomerism of 2-alkyl-5-hexyl-1,3-dioxanes
  • A. V. Bogatskii
  • Z. D. Bogatskaya
  • Yu. Yu. Samitov
  • A. A. Andreeva
Article
  • 25 Downloads

Abstract

2-Methyl-5-hexyl- and 2-isopropyl-5-hexyl-1, 3-dioxanes have been synthesized for the first time by the condensation of 2-hexyl-1, 3-propane-diol with acetaldehyde and isobutyraldehyde, and they have been separated into their stereoisomers by fractionation in efficient columns. It has been shown by a study of their PMR spectra that the low-boiling isomers have the cis- and the high-boiling isomers the trans-configuration. A study of the PMR spectra has enabled us to show not only the configuration but also the predominant conformations of the isomers; the cis-isomer exists predominantly in the unsymmetrical boat conformation with a diequatorial location of the substituents and the trans-isomer in the chair conformation, also with a diequatorial arrangement of the substituents.

Keywords

Acetaldehyde Organic Chemistry Fractionation Chair Conformation Efficient Column 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    A. V. Bogatskii, Yu. Yu. Samitov, N. L. Garkovik, and S. A. Andronati, KhGS [Chemistry of Heterocyclic Compounds], 2, 674, 1966.Google Scholar
  2. 2.
    A. V. Bogatskii and N. L. Garkovik, ZhOKh, collection 2, p. 42, 1965.Google Scholar
  3. 3.
    C. Barbier, I. Delman, and T. Ranft, Tetrah. Let., 3339, 1964.Google Scholar
  4. 4.
    J. Delman and C. Barbier, J. Chem. Phys., 41, 1106, 1964.Google Scholar
  5. 5.
    H. Conroy, Adum. Org. Chem., [Russian translation], 265, 1960.Google Scholar
  6. 6.
    H. Gutowski, M. Karplus, and D. Granti, J. Chem. Phys., 31, 1278, 1959.Google Scholar
  7. 7.
    A. V. Bogatskii, Yu. Yu. Samitov, and N. L. Garkovik, ZhOrKh, 2, 1335, 1966.Google Scholar
  8. 8.
    M. Conrad and C. Bischoff, Ann., 204, 143, 1880.Google Scholar
  9. 9.
    E. Wiberg and M. Schmidt, Z. Naturforsch, 76-b, 59, 1952.Google Scholar
  10. 10.
    Z. D. Bogatskaya, Ti Fu-pao, V. E. Ivashchenko, and A. F. Galatin, ZhOKh, 32, 2282, 1962.Google Scholar

Copyright information

© Consultants Bureau 1971

Authors and Affiliations

  • A. V. Bogatskii
    • 1
    • 2
  • Z. D. Bogatskaya
    • 1
    • 2
  • Yu. Yu. Samitov
    • 1
    • 2
  • A. A. Andreeva
    • 1
    • 2
  1. 1.Mechnikov Odessa State UniversityUSSR
  2. 2.Ul'yanov-Lenin Kazan State UniversityUSSR

Personalised recommendations