Donor-Acceptor Adducts of a 1,3-Disila-2-oxyallyl Zwitterion

Michael J. Cowley, Volker Huch, David Scheschkewitz*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

In the presence of a Lewis acid or base, cyclotrisilene cSi3Tip4 (Tip=2,4,6-triisopropylphenyl) reacts with CO to form stable adducts of a 1,3-disila-2-oxyallyl zwitterion. Coordination of an N-heterocyclic carbene (NHC) to one silicon center results in a localized Si=C bond, where-as B(C6F5)3 bonds to the carbonyl moiety leading to the delocalization of the positive charge over the oxyallyl moiety. Computational analysis of the electronic structure of the Lewis acid adduct reveals a considerable interaction between the two silicon atoms in 1,3-position and thus aromaticity akin to the homocyclopropenium cation.

Original languageEnglish
Pages (from-to)9221-9224
Number of pages4
JournalChemistry - A European Journal
Volume20
Issue number30
Early online date14 May 2014
DOIs
Publication statusPublished - 21 Jul 2014

Keywords

  • density functional calculations
  • donor-acceptor systems
  • silicon
  • small molecule activation
  • small ring systems
  • ALLYL CATIONS
  • DOUBLE-BOND
  • CYCLOTRISILENES
  • MOLECULES
  • SILICON
  • KETONE
  • SILYL

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