Monatshefte für Chemie / Chemical Monthly

, Volume 120, Issue 8–9, pp 735–742 | Cite as

Stereochemie und1H-NMR-Spektren einiger vom Pentaerythrit abgeleiteten Spiro-1,3-dioxane

  • Sorin Mager
  • Mihai Horn
  • Ion Grosu
  • Mircea Bogdan
Organische Chemie Und Biochemie

Stereochemistry and1H-NMR spectra of some spiro-1,3-dioxanes obtained from pentaerythritol

Summary

Mono- and trispiro-1,3-dioxanes with mobile, fixed and “semimobile” structures were obtained by the condensation reaction of pentaerythritol with aldehydes and symmetrical or unsymmetrical ketones. The conformational analysis of the obtained compounds was undertaken by means of1H-NMR spectroscopy. The spiro-1,3-dioxanes obtained with aldehydes or nonsymmetrical ketones represent fixed (“anancomeric”) structures. Ketalisation with 4-t-butyl-cyclohexanone leads to a “semimobile” structure of a trispiro-1,3-dioxane in which the two marginal cyclohexanic rings are fixed, while the two middle ones are mobile, continuously flipping at room temperature. The solvent effect on the NMR spectra is also discussed. Utilisation of benzene-d6 makes it possible to interpret some of the complex spectra with superposed signals on the basis of the aromatic solvent induced shift (ASIS).

Keywords

Spiro-1,3-dioxanes Pentaerythritol (a)ketals Conformational analysis Aromatic solvent induced shift — ASIS 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literatur

  1. [1]
    Mager S., Eliel E. L. (1973) Rev. Roum. Chim.18: 1379Google Scholar
  2. [2]
    Mager S., Eliel E. L. (1973) Rev. Roum. Chim.18: 2097Google Scholar
  3. [3]
    Binsch G., Eliel E. L., Mager S. (1973) J. Org. Chem.38: 4079Google Scholar
  4. [4]
    Mager S., Hopârtean I., Horn M., Grosu I. (1979) Stud. Univ. Babeş-Bolyai, Chem.24: 32Google Scholar
  5. [5]
    Mager S., Tăranu R., Horn M., Mureşan M. (1982) Monatsh. Chem.113: 565Google Scholar
  6. [6]
    Lapuka L. F., Kantor E. A., Musavirov R. S., Rakhmankulov D. L. (1981) Zh. Obshch. Khim.51: 934Google Scholar
  7. [7]
    Eliel E. L. (1972) Angew. Chem.84: 779; Eliel E. L. (1972) Angew. Chem., Int. Ed. Engl.11: 739Google Scholar
  8. [8]
    Laszlo P. (1967) In: Emsley J. W., Feeney J., Sutcliffe L. H. (eds.) Progress in NMR Spectroscopy, Vol. 3. Pergamon Press, Oxford, S. 231Google Scholar
  9. [9]
    Anderson J. E. (1965) Tetrahedron Lett.: 4713Google Scholar
  10. [10]
    Mager S., Horn M. (unveröffentlicht)Google Scholar
  11. [11]
    Orthner L. (1928) Ber. Dtsch. Chem. Ges.61: 116Google Scholar
  12. [12]
    Moshchinskaya N. K., Stratienko V. T., Chekhuta O. M. (1965) Pat. UdSSR 173237; (1966) C. A.64: 652 cGoogle Scholar
  13. [13]
    Skrabal A., Zlatewa M. (1926) Z. physik. Chem.119: 305Google Scholar
  14. [14]
    Nec R. (1971) Chem. Prumyse21: 67Google Scholar
  15. [15]
    Read J. (1912) J. Chem. Soc.101: 2090Google Scholar
  16. [16]
    Klyushnik N. P. (1964) Ukr. Khim. Zh.30: 965Google Scholar

Copyright information

© Springer-Verlag 1989

Authors and Affiliations

  • Sorin Mager
    • 1
  • Mihai Horn
    • 1
  • Ion Grosu
    • 1
  • Mircea Bogdan
    • 2
  1. 1.Fakultät für Technologische ChemieUniversität Cluj-NapocaRumänien
  2. 2.Institut für Isotopische und Molekulare TechnologieCluj-NapocaRumänien

Personalised recommendations