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The Trichlorovinylsilane/tert-Butyllithium ReagentsA Source for Transient Silenes?

Summary: The Trichlorovinylsilane/tert-Butyllithium ReagentsA
Source for Transient Silenes?
Thomas Mušller, Michael Bendikov, Norbert Auner, and Yitzhak Apeloig*,
Institut fušr Anorganische Chemie der Goethe-Universitašt Frankfurt am Main,
Marie-Curie Strasse 11, 60439 Frankfurt, Federal Republic of Germany, and Department of
Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry,
Technion-Israel Institute of Technology, 32000 Haifa, Israel
Received September 27, 2000
Summary: Quantum-mechanical calculations suggest
that silenes are probably not involved as intermediates
in the reaction of the trichlorovinylsilane/t-BuLi reagent
with alkynes. Instead, the product 7 is obtained via a
carbometalation-elimination reaction.
The reaction of trichlorovinylsilane (1) with t-BuLi in
the presence of suitable scavengers provides a facile
approach to silaheterocycles, i.e., 2 and 3 (eq 1), which
serve as precursors to novel silicon-containing organic
molecules with new, exciting properties.1
The formation of silaheterocycles in these reactions
was generally rationalized by the intermediate forma-


Source: Apeloig, Yitzhak - Department of Chemistry, Technion, Israel Institute of Technology


Collections: Chemistry