Synthesis of an NHC-Coordinated Dialkyldisilavinylidene and Its Oxidation Providing a Silicon Analog of an Acetolactone

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Abstract

Although isolable silicon analogs of acetylene have been extensively studied, the silicon analogs of vinylidene, which is a short-lived isomer of acetylene, remain scarce. Herein, we report isolable NHC-coordinated dialkyldisilavinylidene 1 synthesized by the reduction of a tetrabromodisilane featuring a bulky alkyl protecting group. 1 was fully characterized by a combination of multinuclear NMR spectroscopy, high-resolution mass spectrometry, elemental analysis, and X-ray diffraction analysis. The UV-vis spectrum and DFT calculations disclosed that 1 possesses an SiaSi double bond and lone pair electrons on the terminal Si atom coordinated by the NHC. 1 reacted with N2O and B(C6F5)3 to provide a silicon analog of an acetolactone stabilized by a Lewis base and a Lewis acid (4).

Original languageEnglish
Pages (from-to)843-847
Number of pages5
JournalOrganometallics
Volume40
Issue number7
DOIs
Publication statusPublished - 2021 Apr 12

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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