Chapter 60. The Acid-Induced Rearrangement of α-Functionalized Alkylpolysilanes

  1. Prof. Norbert Auner2 and
  2. Prof. Johann Weis3
  1. F. Luderer,
  2. H. Reinke and
  3. H. Oehme

Published Online: 28 APR 2008

DOI: 10.1002/9783527619917.ch60

Organosilicon Chemistry IV: From Molecules to Materials

Organosilicon Chemistry IV: From Molecules to Materials

How to Cite

Luderer, F., Reinke, H. and Oehme, H. (2000) The Acid-Induced Rearrangement of α-Functionalized Alkylpolysilanes, in Organosilicon Chemistry IV: From Molecules to Materials (eds N. Auner and J. Weis), Wiley-VCH Verlag GmbH, Weinheim, Germany. doi: 10.1002/9783527619917.ch60

Editor Information

  1. 2

    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. 3

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

Author Information

  1. Fachbereich Chemie der Universität Rostock D-18051 Rostock, Germany Tel.: Int. code + (381)498 1765 — Fax: Int. code + (381)498 1763

Publication History

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

ISBN Information

Print ISBN: 9783527298549

Online ISBN: 9783527619917

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Keywords:

  • polysilanes;
  • rearrangements;
  • silylium ion;
  • carbenium ion

Summary

In the presence of acids, α-functionalized alkylpolysilanes undergo a rapid rearrangement, a 1, 2-Si, C exchange, which is interpreted as an acid-catalyzed abstraction of the respective functional group (e.g. OSiMe3, OH, Cl) from the alkylpolysilane derivative affording a polysilanyl carbenium ion, which stabilizes under 1, 2-migration of one trimethylsilyl group and nucleophilic attack of the conjugate base of the acid used to give the thermodynamically favored product.