Skip to main content
SpringerLink
Log in

Gezielte Konformationsänderungen an cyclischen Systemen, 2. Mitt.: Konformere 2-Phenyl-1,3-dithiane

Selective conformational changes of cyclic systems, II: Conformers of 2-phenyl-1.3-dithianes

  • Organische Chemie und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

In 2-phenyl-1.3-dithiane (1) and its p-methyl derivative (2) theequatorial phenyl adopts a conformation coinciding with the symmetry plane of the molecule. For 2-(2′-methylphenyl)-1.3-dithiane (4) acisoid relation of theaxial hydrogen on C-2 and the aromatic methyl group was established. This conformation can be changed by substitution of position 2 by methyl: in this geminally substituted compound (3), phenyl no longer assumes theequatorial position, and the plane of the phenyl group isperpendicular to the symmetry plane of the molecule. These deductions depend on the deshielding effect of sulphur and the diamagnetic anisotropy of the aromatic ring in the NMR spectra influencing the chemical shifts of the orthoprotons and of the protons of the dithiane ring respectively. The influence of the conformation on both of these effects is taken into account.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. G. Riddell, Quart. Rev. Chem. Soc. [London]21, 364 (1967).

    Google Scholar 

  2. P. Groth, Acta Chem. Scand.18, 1301 (1964).

    Google Scholar 

  3. E. Langer undH. Lehner, Tetrahedron Letters1974, 1357.

  4. C. Glotzmann, E. Haslinger, E. Langer undH. Lehner, Mh. Chem.106, 187 (1975).

    Google Scholar 

  5. P. Laszlo undP. Stang, Organic Spectroscopy-Principles and Applications. New York: Harper and Row. 1971.

    Google Scholar 

  6. T. Schaefer undT. Yonemoto, Canad. J. Chem.42, 2318 (1964).

    Google Scholar 

  7. A. D. Buckingham, T. Schaefer undW. G. Schneider, J. Chem. Phys.32, 1227 (1960).

    Google Scholar 

  8. E. L. Eliel undR. O. Hutchins, J. Amer. Chem. Soc.91, 2703 (1969).

    Google Scholar 

  9. H. Kalff undC. Romers, Acta Cryst.20, 490 (1966).

    Google Scholar 

  10. N. L. Allinger undM. T. Tribble, Tetrahedron Letters1971, 3259.

  11. N. L. Allinger undC. D. Liang, J. Org. Chem.33, 3319 (1968).

    Google Scholar 

  12. J. P. Mazaleyrat undZ. Welvart, Chem. Commun.1969, 485.

  13. H. Friebolin, S. Kabuss, W. Maier undA. Lüttringhaus, Tetrahedron Letters1962, 683.

  14. C. A. Johnson undF. A. Bovey, J. Chem. Phys.29, 1012 (1958).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Lehrkanzel für Organische Chemie Organisch-Chemisches Institut, Universität Wien, Währinger Straße 38, A-1090, Wien, Österreich

    Elisabeth Langer &  Harald Lehner

Authors
  1. Elisabeth Langer
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Harald Lehner
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Mit 4 Abbildungen

1. Mitt.:H. Lehner, Mh. Chem.105, 895 (1974).

Rights and permissions

Reprints and permissions

About this article

Cite this article

Langer, E., Lehner, H. Gezielte Konformationsänderungen an cyclischen Systemen, 2. Mitt.: Konformere 2-Phenyl-1,3-dithiane. Monatshefte für Chemie 106, 175–185 (1975). https://doi.org/10.1007/BF00914511

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00914511

Search

Navigation