Get access

Taming a Functional Group: Creating Air-Stable, Chiral Primary Phosphanes

Authors

  • Rachel M. Hiney,

    1. School of Chemistry and Chemical Biology, Centre for Synthesis and Chemical Biology, Conway Institute for Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland, Fax: (+353) 1-716-2127
    Search for more papers by this author
  • Lee J. Higham Dr.,

    1. School of Chemistry and Chemical Biology, Centre for Synthesis and Chemical Biology, Conway Institute for Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland, Fax: (+353) 1-716-2127
    2. Current address: School of Natural Sciences-Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK
    Search for more papers by this author
  • Helge Müller-Bunz Dr.,

    1. School of Chemistry and Chemical Biology, Centre for Synthesis and Chemical Biology, Conway Institute for Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland, Fax: (+353) 1-716-2127
    Search for more papers by this author
  • Declan G. Gilheany Dr.

    1. School of Chemistry and Chemical Biology, Centre for Synthesis and Chemical Biology, Conway Institute for Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland, Fax: (+353) 1-716-2127
    Search for more papers by this author

  • We thank the Irish Research Council for Science, Engineering, and Technology (IRCSET) for a scholarship for R.M.H. and the EU for a Marie Curie Host Development Fellowship (HMPD-CT-2000-00053) for L.J.H. We also thank Prof. R. O'Neill for electrochemistry advice and apparatus as well as Dr. G. Docherty (Rhodia) for discussions on phenylphosphane.

Abstract

original image

No rings of fire! Enantiopure primary phosphanes have been developed which are remarkably stable to air oxidation in both solid and solution states (see example). This new class of stable ligand synthon appears to owe its stability to conjugation in their aryl backbones with the extended π ring system. Even one extra ring is good enough.

Get access to the full text of this article

Ancillary