Synthesis 2006(9): 1408-1414  
DOI: 10.1055/s-2006-926430
PAPER
© Georg Thieme Verlag Stuttgart · New York

2-Lithioindenyllithium: An Easily Accessible Intermediate for the One-Pot Synthesis of Single- and Double-Functionalised 2-Indene Derivatives

Edwin G. Ijpeij*, Gert-Jan M. Gruter
DSM Research, P.O. Box 18, 6160 MD Geleen, The Netherlands
Fax: +31(4647)63949; e-Mail: edwin.ijpeij@dsm.com;
Further Information

Publication History

Received 29 September 2005
Publication Date:
11 April 2006 (eFirst)

Abstract

We found that double-silicon-bridged bisindenyl complexes of early transition metals of group 4 are able to produce polyethylenes with high molecular weights and narrow molecular-weight distributions having high α-olefin incorporation. The bottle-neck for the synthesis of these complexes is the ligand synthesis. The corresponding ligands could be obtained via a three-step procedure with low (15%) overall yields. We found that the use of the new 2-lithioindenyllithium enhanced the overall yield to 50% in a one-pot procedure.

    References

  • 2 Wang B, and Gruter GJM. inventors; (DSM) Patent Appl. WO  02079272.  Chem. Abstr. 2002, 137, 777999
  • 4 Hedberg FC. Rosenberg H. Tetrahedron Lett.  1969,  4011 
  • 5 Eliasson B. Edlund U. J. Chem. Soc., Perkin Trans. 2  1981,  403 
  • 6 Rhine W. Stucky GD. J. Am. Chem. Soc.  1975,  97:  737 
  • 8 MacDowell DWH. Lindley WA. J. Org. Chem.  1982,  47:  705 
  • 9a Weidler A.-M. Bergson G. Acta Chem. Scand.  1964,  18:  1484 
  • 9b Weidler A.-M. Bergson G. Acta Chem. Scand.  1964,  18:  1487 
1

Currently employed with Avantium Technologies Amsterdam.

3

Yields determined by 1H NMR of the crude reaction mixture.

7

Wang, B.; unpublished results.