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A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
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Published on: November 12, 2016

Persistent dialkyl(silyl)stannylium ions.

Annemarie Schäfer1, Wolfgang Saak, Detlev Haase

  • 1Institut für Reine und Angewandte Chemie, Carl von Ossietzky Universität Oldenburg, Carl-von-Ossietzky-Strasse 9-11, D-26111 Oldenburg, Federal Republic of Germany.

Journal of the American Chemical Society
|August 16, 2011
PubMed
Summary

Researchers synthesized dialkyl(silyl)stannylium borates. Experimental and theoretical data revealed these stannylium ions are not stabilized by β-silyl hyperconjugation or C-H/Sn(+) interactions.

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Area of Science:

  • Organometallic Chemistry
  • Main Group Chemistry
  • Boron Chemistry

Background:

  • Stable stannylenes are valuable synthetic intermediates.
  • Silyl-substituted stannylenes offer unique reactivity pathways.
  • Borate anions like tetrakis(pentafluorophenyl)borate are weakly coordinating and useful counterions.

Purpose of the Study:

  • To report the synthesis of novel dialkyl(silyl)stannylium borates.
  • To investigate the electronic structure and bonding in these stannylium species.
  • To determine the factors responsible for the stabilization of the stannylium ion.

Main Methods:

  • Reaction of a β-silyl-substituted stannylene with silylarenium borates.
  • Characterization using Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Single-crystal X-ray diffraction analysis.
  • Quantum mechanical calculations.

Main Results:

  • Successful synthesis of dialkyl(silyl)stannylium borates was achieved.
  • Structural analysis confirmed the proposed stannylium structure.
  • Computational studies provided insights into electronic distribution and bonding.
  • Evidence suggests that β-silyl hyperconjugation does not stabilize the stannylium ion.
  • Intramolecular C-H/Sn(+) interactions were found to be insignificant.

Conclusions:

  • Dialkyl(silyl)stannylium borates can be synthesized from stable stannylene precursors.
  • The electronic structure indicates a lack of stabilization from common hyperconjugative effects.
  • Alternative stabilization mechanisms, if any, require further investigation.