Isolation of silenolates (R3Si)2Si=C(OLi)Ad with a doubly bonded silicon atom

Roman Dobrovetsky*, Lieby Zborovsky, Dennis Sheberla, Mark Botoshansky, Dmitry Bravo-Zhivotovskii, Yitzhak Apeloig

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


(Figure Presented) The first enol silenolates, (tBuMe2Si) 2Si= C(OLi)Ad and (tBu2MeSi)2Si=C(OLi)Ad, were synthesized and characterized by X-ray spectroscopy. Calculations show that, in contrast to organic enolates, which exist predominantly in the enol form regardless of solvation, the enol form of silenolates (left) is favored in nonpolar solvents, and the keto form (right) when strongly solvated. Ad = 1-adamantyl.

Original languageEnglish
Pages (from-to)4084-4087
Number of pages4
JournalAngewandte Chemie - International Edition
Issue number24
StatePublished - 1 Jun 2010
Externally publishedYes


  • Density functional calculations
  • Enols
  • Silenes silicon
  • Tautomerism


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