Equilibrium between a cyclotrisilene and an isolable base adduct of a disilenyl silylene

Michael J. Cowley, Volker Huch, Henry S. Rzepa*, David Scheschkewitz

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

In organic chemistry, compounds with adjacent alkene and carbene functionalities (vinyl carbenes) are studied widely as fleeting intermediates and in the coordination sphere of transition metals. Stable derivatives of vinyl carbenes remain elusive, including the corresponding heavier group 14 homologues. Here we report the isolation and full characterization of a base-stabilized silicon version of a vinyl carbene that features a silicon-silicon double bond as well as a silylene functionality, coordinated by an N-heterocyclic carbene (NHC). In solution, the intensely green disilenyl silylene adduct exists in equilibrium with the corresponding silicon analogue of a cyclopropene and free NHC, which was quantified by nuclear magnetic resonance spectroscopy and ultraviolet-visible spectroscopy. The reversibility of this process raises exciting possibilities for the preparation of extended conjugated pi systems of silicon.

Original languageEnglish
Pages (from-to)876-879
Number of pages4
JournalNature Chemistry
Volume5
Issue number10
DOIs
Publication statusPublished - Oct 2013

Keywords

  • CARBENE
  • SILICON
  • BONDS
  • CHEMISTRY
  • ISOMERS
  • ANALOGS

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