Chapter 21. Intramolecularely π-Stabilized Silyl Cations

  1. Prof. Norbert Auner3 and
  2. Prof. Johann Weis4
  1. Norbert Auner1,
  2. Thomas Müller1,
  3. Markus Ostermeier1,
  4. Julia Schuppan2 and
  5. Hans-Uwe Steinberger2

Published Online: 28 APR 2008

DOI: 10.1002/9783527619917.ch21

Organosilicon Chemistry IV: From Molecules to Materials

Organosilicon Chemistry IV: From Molecules to Materials

How to Cite

Auner, N., Müller, T., Ostermeier, M., Schuppan, J. and Steinberger, H.-U. (2000) Intramolecularely π-Stabilized Silyl Cations, in Organosilicon Chemistry IV: From Molecules to Materials (eds N. Auner and J. Weis), Wiley-VCH Verlag GmbH, Weinheim, Germany. doi: 10.1002/9783527619917.ch21

Editor Information

  1. 3

    Inst. für Anorganische Chemie, der Universität Frankfurt, Marie-Curie-Strasse 11, D-60439 Frankfurt am Main, Germany, Phone: 0 69/7 98-29180, -29591, Fax: 069/798-29188

  2. 4

    Wacker-Chemie GmbH, Geschäftsbereich S, Werk Burghausen, Johannes-Hess-Strasse 24, D-84489 Burghausen, Germany

Author Information

  1. 1

    Institut für Anorganische Chemie Johann Wolfsang Goethe-Universität Frankfurt Marie-Curie-Str.11, D-60439 Frankfurt am Main, Germany Tel: Int. code + (69)798 29180 — Fax: Int. code f (69)798 29188

  2. 2

    Fachinstitut für Anorganische Chemie der Humboldt Universität Berlin Hessische Str. 1–2, D-10115 Berlin, Germany

Publication History

  1. Published Online: 28 APR 2008
  2. Published Print: 17 JAN 2000

ISBN Information

Print ISBN: 9783527298549

Online ISBN: 9783527619917



  • silyl cations;
  • ab initio calculations;
  • density functional calculations;
  • NMR spectroscopy;
  • silanorbornenes;
  • silanorbornadienes


The synthesis of intramolecularely π-stabilized silylium ions such as 7-sila-norbomadienyl- and 2-silanorbornyl cations was attempted. While benzo-7-sila-norbomadienyl cation 7 could not be detected at room temperature in hydrocarbon solvents, its donor-acceptor complex 8 was identified by NMR spectroscopy. In contrast, persistent 2-silanorbomyl cations could be synthesized and characterized by NMR spectroscopy and modem quantum chemical methods. Silanorbornyl cations 5 and 25 are stable at room temperature and have a bridged structure in which the silicon adopts a [3+2] coordination.