Stable Silenolates and Brook-Type Silenes with Exocyclic Structures

Michael Haas, Roland Fischer, Michaela Flock, Stefan Müller, Martin Rausch, Robert Saf, Ana Torvisco Gomez, Harald Stüger*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


The first silenolates with exocyclic structures [(Me3Si)2Si(Si2Me4)2SiC(R)O]−K+ (2a: R = 1-adamantyl; 2b: mesityl; 2c: o-tolyl) were synthesized by the reaction of the corresponding acylcyclohexasilanes 1a–c with KOtBu. NMR spectroscopy and single-crystal X-ray diffraction analysis suggest that the aryl-substituted silenolates 2b,c exhibit increased character of functionalized silenes as compared to the alkyl-substituted derivative 2a due to the different coordination of the K+ counterion to the SiC(R)O moiety. 2b,c, thus, reacted with ClSiiPr3 to give the exocyclic silenes (Me3Si)2Si(Si2Me4)2Si═C(OSiiPr3)R (3b: R = Mes; 3c: o-Tol), while 2a afforded the Si-silylated acylcyclohexasilane 1d. The thermally remarkably stable compound 3b, which is the first isolated silene with the sp2 silicon atom incorporated into a cyclopolysilane framework, could be fully characterized structurally and spectroscopically.
Original languageEnglish
Pages (from-to)5956-5959
Issue number21
Publication statusPublished - 2014

Fields of Expertise

  • Advanced Materials Science

Treatment code (Nähere Zuordnung)

  • Basic - Fundamental (Grundlagenforschung)


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