Chapter 19. Hexaaryltetrasilabuta-1, 3-Diene: Synthesis and Some Reactions

  1. Prof. Norbert Auner2 and
  2. Prof. Johann Weis3
  1. Stefan Willms and
  2. Manfred Weidenbruch

Published Online: 28 APR 2008

DOI: 10.1002/9783527619917.ch19

Organosilicon Chemistry IV: From Molecules to Materials

Organosilicon Chemistry IV: From Molecules to Materials

How to Cite

Willms, S. and Weidenbruch, M. (2000) Hexaaryltetrasilabuta-1, 3-Diene: Synthesis and Some Reactions, in Organosilicon Chemistry IV: From Molecules to Materials (eds N. Auner and J. Weis), Wiley-VCH Verlag GmbH, Weinheim, Germany. doi: 10.1002/9783527619917.ch19

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, Universität Oldenburg Carl-von-Ossietzky-Straße 9, D-26111 Oldenburg, Germany Tel.: Int. code + (441)798 3655 — Fax: Int. code + (441)798 3352

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:

  • disilenes;
  • tetrasilabutadiene;
  • oxidation reactions;
  • hydrolysis reactions

Summary

Hexakis(2, 4, 6-triisopropylphenyl)tetrasilabuta-1, 3-diene (12), the first molecule containing conjugated Si-Si double bonds, was prepared according to the following reaction sequence. Treatment of tetrakis(2, 4, 6-triisopropylphenyl)disilene with excess lithium furnished the disilenyllithium compound 10. In the second step half of 10 reacted with mesityl bromide to give the bromodisilene 11. Intermolecular LiBr elimination from 10 and 11 afforded the butadiene s-cis-12 in the form of reddish brown crystals. On account of the large 1, 4-separation of the silicon atoms, all attempted [4+2] cycloadditions of 12 with several alkenes failed. However, reactions of 12 with water, atmospheric oxygen, and m-chloroperbenzoic acid yielded the corresponding hydrolysis and oxidation products including the oxatetrasilacyclopentane ring system 16 analogous to tetrahydrofuran.