Chapter 14. Synthesis, Structure and Reactivity of Intramolecularly Donor-Stabilized Silenes

  1. Prof. Dr. Norbert Auner3 and
  2. Prof. Dr. Johann Weis4
  1. Martin Mickoleit1,
  2. Matthias Pötter1,
  3. Ute Bäumer1,
  4. Kathleen Schmohl1,
  5. Hartmut Oehme1 and
  6. Rhett Kempe2

Published Online: 5 MAY 2008

DOI: 10.1002/9783527619924.ch14

Organosilicon Chemistry V: From Molecules to Materials

Organosilicon Chemistry V: From Molecules to Materials

How to Cite

Mickoleit, M., Pötter, M., Bäumer, U., Schmohl, K., Oehme, H. and Kempe, R. (2003) Synthesis, Structure and Reactivity of Intramolecularly Donor-Stabilized Silenes, in Organosilicon Chemistry V: From Molecules to Materials (eds N. Auner and J. Weis), Wiley-VCH Verlag GmbH, Weinheim, Germany. doi: 10.1002/9783527619924.ch14

Editor Information

  1. 3

    Department of Inorganic Chemistry, University of Frankfurt, Marie-Curie-Straße 11, 60439 Frankfurt am Main, Germany

  2. 4

    Consortium of Electrochemical Industry GmbH, Zielstattstraße 20, 81379 Munich, Germany

Author Information

  1. 1

    Fachbereich Chemie der Universitat Rostock, D-18051 Rostock, Germany Tel: +49 381 498 1765 — Fax: +49 381 498 1763

  2. 2

    Institut für Organische Katalyseforschung an der Universität Rostock, Germany

Publication History

  1. Published Online: 5 MAY 2008
  2. Published Print: 26 SEP 2003

ISBN Information

Print ISBN: 9783527306701

Online ISBN: 9783527619924

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Keywords:

  • silanes;
  • silenes;
  • donor-acceptor systems;
  • structure elucidation

Summary

Using a new synthetic pathway, four intramolecularly donor-stabilized silenes, R(Me3Si)Si[DOUBLE BOND]C(SiMe3)2 (10: R = 8-dimethylamino-1-naphthyl; 11: R = 2 -(dimethylaminomethyl)phenyl; 14: R = 2,6–bis(dimethylaminomethyl)phenyl; 15: R = 2,6–bis(diethylaminomethyl)phenyl)), were prepared by the reaction of (dichloromethyl)tris(trimethylsilyl)silane (1c) with the respective dialkylamino substituted aryllithium compounds (molar ratio 1:2). X-ray structural analyses of the four silenes revealed strong donor-acceptor interactions between the dialkylamino groups and the electrophilic silene silicon atoms, leading to pyramidalization at the silicon centers. The configuration at the silene carbon atoms was found to be planar. The chemical behavior of the new silenes, particularly reactions with water and methanol, treatment with methyl iodide or methyl triflate and conversions with benzaldehyde, are discussed.