Skip to main content
SpringerLink
Log in

8,8′-Bis(diphenylphosphinomethyl)-1,1′-binaphthyl. Synthese und Konformation

8,8′-Bis(diphenylphosphinomethyl)1,1′-binaphthyl. Synthesis and conformation (short commun.)

Kurze Mitteilung

  • Organische Chemie Und Bicchemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

The title compound3 was prepared from 8,8′-Bis(bromomethyl)-1,1′-binaphthyl (1) in two steps in approx. 10% overall yield. The crystal structure of the intermediate phosphinoxide2 was determined. Attempts to prepare chelate complexes of3 with Ni(II) or Pd(II) failed.

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

Literatur und Daten

  1. Noyori R., Kitamura M. (1989) Modern Synthetic Methods 1989; Scheffold R. (ed.). Springer, Berlin Heidelberg New York Tokyo, S. 115

    Google Scholar 

  2. Ojima I., Clos N., Bastos C. (1989) Tetrahedron45: 6901

    Google Scholar 

  3. Brunner H. (1988) In: Eliel E. L., Wilen S. H. (eds.). Top. Stereochem.18: 129.

    Google Scholar 

  4. Noyori R., Takaya H. (1990) Acc. Chem. Res.23: 345

    Google Scholar 

  5. Kyba E. P., Gokel G. W., deJong F., Koga K., Sousa L. R., Siegel M. G., Kaplan L., Sogah G. D. Y., Cram D. J. (1977) J. Org. Chem.42: 4173

    Google Scholar 

  6. Brown K. J., Berry M. S., Murdoch J. R. (1985) J. Org. Chem.50: 4345

    Google Scholar 

  7. Maygrot N., Mazaleyrat J.-P. (1985) Synthesis1985: 317

    Google Scholar 

  8. Hall D. M., Ridgewell S., Turner E. E. (1954) J. Chem. Soc.1954: 2498

    Google Scholar 

  9. Badar Y., Cooke A. S., Harris M. M. (1965) J. Chem. Soc.1965: 1412

    Google Scholar 

  10. Kagan H. B. (1985) In: Morrison, J. D. (ed.) Asymmetirc Synthesis Bd5: S. 4

  11. Harris M. M., Singh S. (1976) J. Chem. Soc. (Perkin Trans. II)1976: 793

    Google Scholar 

  12. Harris M. M., Patel P. K. (1977) J. Chem. Soc. (Perkin Trans. II)1977: 304

    Google Scholar 

  13. Tamao K., Yamamoto H., Masumoto H., Miyake N., Hayashi T., Kumada M. (1977) Tetrahedron Lett.1977: 1389

    Google Scholar 

  14. vgl. z.B. Harvey R. G. DeSombre E. R. (1964) Grayson M., Griffith E. J. (eds.) Top. Phosphorus Chem., Vol. 1. Interscience, Wiley, New York, p 57

    Google Scholar 

  15. „peri-Effekte“ [13]: C10-C1-C24 125.2°, C33-C24-C1 125.1°;, C10-C9-C11 126.2°;, C33-C32-C34 124.8 °;, C5-C10-C1-C24 179.0°;, C28-C33-C24-C1 173.8°;, C5-C10-C9-C11 175.0°;, C28-C33-C32-C34 172.6°; vgl. auch Balasubramaniyan, V. (1966) Chem. Rev.66: 567

    Google Scholar 

  16. Korp J. D., Bernat I., Harris M. M. und Patel P. K. (1981) J. Chem. Soc. (Perkin Trans. II), 1621.

Download references

Author information

Authors and Affiliations

  1. Institut für Organische Chemie, Universität Wien, A-1090, Wien, Österreich

    Michael Widhalm

  2. Institut für Physikalische Chemie, Universität Graz, A-8010, Graz, Österreich

    Christoph Kratky

Authors
  1. Michael Widhalm
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Christoph Kratky
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Widhalm, M., Kratky, C. 8,8′-Bis(diphenylphosphinomethyl)-1,1′-binaphthyl. Synthese und Konformation. Monatsh Chem 124, 103–108 (1993). https://doi.org/10.1007/BF00808514

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00808514

Keywords

Search

Navigation