Summary: Silicon Enolate Analogues
Isolation of Silenolates (R3Si)2Si=C(OLi)Ad with a Doubly Bonded
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.
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.
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 crown-6.
Silenolates also exist in