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Synth. methods III
Synthetic methods
Named Reactions
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The Saucy-Marbet reaction
26 November 2008 - named reactions
What
: The Saucy-Marbet rearrangement
Who
: G. Saucy & R. Marbet (Hoffmann-La Roche) 1967 (
DOI
)
Why
: formation of a beta
keto
allene
by reaction of a
propargyl
alcohol
with an
alkenyl
ether
by heat or
acid catalysis
.
Mechanism
: the basic
reaction mechanism
is a variation of the
Claisen rearrangement
not with an
alkene
but with an
alkyne
.
Also known as
: propargyl Claisen rearrangement. Actually preceded by earlier work by Black & Landor in 1965 (
DOI
)
Industrial applications
: synthesis of beta -
ionone
starting from
Dehydrolinalool
and
ethyl acetoacetate
(
Link
)
Scope
: a 2002 patent (
Link
) describes synthesis of a
geranyl
acetone
.
The reaction can be
catalyzed by gold
(
DOI
):
An example of a
stereospecific
reaction is provided by Hsung in 2008 (
DOI
):
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