NNNS chemistry blog
April 2018
March 2018
February 2018
January 2018
December 2017
November 2017
October 2017
September 2017
August 2017
July 2017
June 2017
All blogs
May 2017
April 2017
March 2017
February 2017
January 2017
December 2016
November 2016
October 2016
September 2016
August 2016
July 2016
June 2016
May 2016
April 2016
Contact
March 2016
February 2016
January 2016
December 2015
November 2015
October 2015
September 2015
August 2015
July 2015
June 2015
May 2015
April 2015
March 2015
February 2015
January 2015
December 2014
November 2014
October 2014
September 2014
August 2014
July 2014
June 2014
May 2014
April 2014
March 2014
February 2014
January 2014
December 2013
November 2013
October 2013
September 2013
August 2013
July 2013
June 2013
May 2013
April 2013
March 2013
February 2013
January 2013
December 2012
November 2012
October 2012
September 2012
August 2012
July 2012
June 2012
May 2012
April 2012
March 2012
February 2012
January 2012
Synth. methods III
Synthetic methods
Named Reactions
Archive
Internet
Admin
RSS feed
Previous
|
Next
|
All
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
):
Tweet to @NNNS_chemistry
