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Silicon Enolate Analogues DOI: 10.1002/anie.201001024

Summary: Silicon Enolate Analogues
DOI: 10.1002/anie.201001024
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,* and Yitzhak Apeloig*
Dedicated to Professor Paul von RaguĜ Schleyer on the occasion of his 80th birthday
Metal enolates are an important class of reactive intermedi-
ates widely employed in organic synthesis.[1]
In contrast, little
is known about silenolates, the silicon analogues of eno-
Enolates exist in two tautomeric forms, the enol form
and the keto form, and their reactions reflect the coexistence
of these two forms.[1]
The dominant structure of alkali metal
enolates is the enol form both in nonsolvating media and in
various solvating media such as THF, N,N,N',N'-tetramethy-
lethylenediamine, and [18]crown-6.[1]
Silenolates also exist in


Source: Apeloig, Yitzhak - Department of Chemistry, Technion, Israel Institute of Technology


Collections: Chemistry