Chapter 27. Reactions of Trimethylsiloxychlorosilanes (Me3SiO)RPhSiCl (R = H, Me, Et, iPr, iBu, Ph, Mes) with Lithium — Formation and Reactivity of Trimethylsiloxysilyllithiums

  1. Prof. Dr. Norbert Auner2 and
  2. Prof. Dr. Johann Weis3
  1. Jörg Harloff and
  2. Eckhard Popowski

Published Online: 5 MAY 2008

DOI: 10.1002/9783527619924.ch27

Organosilicon Chemistry V: From Molecules to Materials

Organosilicon Chemistry V: From Molecules to Materials

How to Cite

Harloff, J. and Popowski, E. (2008) Reactions of Trimethylsiloxychlorosilanes (Me3SiO)RPhSiCl (R = H, Me, Et, iPr, iBu, Ph, Mes) with Lithium — Formation and Reactivity of Trimethylsiloxysilyllithiums, in Organosilicon Chemistry V: From Molecules to Materials (eds N. Auner and J. Weis), Wiley-VCH Verlag GmbH, Weinheim, Germany. doi: 10.1002/9783527619924.ch27

Editor Information

  1. 2

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

  2. 3

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

Author Information

  1. Fachbereich Chemie, Universität Rostock Albert-Einstein-Straße 3a, D-18059 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:

  • trimethylsiloxysilyllithiums;
  • trimethylsiloxydisilanes;
  • trimethylsiloxy-trisilanes;
  • self-condensation;
  • silylenoids

Summary

Reaction of chlorosilanes (Me3SiO)RPhSiCl (1a: R = H, 1b: R = Me, 1c: R = Et, 1d: R = iPr, 1e: R = tBu, 1f: R = Ph, 1g: R = Mes) with lithium metal in THF at −78 °C and in a mixture of THF/diethyl ether/n-pentane in volume ratio 4:1:1 (Trapp mixture) at −110 °C gives the silyllithium derivatives (Me3SiO)RPhSiLi (2b-g), (Me3SiO)RPhSiRPhSiLi (3a-g), Me3SiRPhSiLi (4a-g) and the trisiloxanes (Me3SiO)2SiRPh (5a-g). The siloxydisilanyllithiums 3a-g are formed by self-condensation of the corresponding siloxysilyllithiums 2a-g. Reaction of (Me3SiO)RPhSiLi (2f: R = Ph, 2g: R = Mes) with n-butyllithium leads to the silyllithiums nBuRPhSiLi (14f, 14g). Silacyclopentene 16 is obtained in the reaction of 2g with 2,3–dimethylbutadiene.