Uses
(Trimethylsilyl)allene is used as propargylic anion equivalent; substrate for ene reaction, participating in the following synthesis reactions Propargylic Anion Equivalent, Synthesis of Silylacetylenes via Ene Reaction etc.
Preparation
Two methods have been reported for the
preparation of (trimethylsilyl)allene [(TMS)allene]). Reductive
deoxygenation of the tosylhydrazone derivative affords the
title compound in 51% yield.4b The tosylhydrazone is readily
prepared from the corresponding aldehyde, which in turn is
accessed by formylation of (trimethylsilyl)ethynylmagnesium
bromide with DMF (eq 1). (TMS)allene has also been prepared
by flash vacuum pyrolysis of methyl (trimethylsilyl)-
propargyl ether, which is obtained from silylation of methyl
propargyl ether (eq 2).
