Jasmone 1 - ChemistforChrist

Synthesis of JASMONE
Synthesis of Hiyama Bull. Chem. Soc. Jpn 1980, 53, 169-173
O
OH
O
HCOOH,
H 3PO 4
Difficult mechanism:
Tautomerization,
Isomerization,
Eliminatation....
For more details consult
literature given.
Some commercially available 5-memebered rings:
O O O
O
O
O
OH
O
is like other 1,3 diketones
in equilibrium with its
enol.
O H
OH
H
O
More resources available at
www.chemistforchrist.de
O
O H
best nucleophile
in the mixture
cyclopentane-1,3-dione
Is an important starting material
for the industrial synthesis of
steroids.
O O
The Keto-Enol Tautomerization can be seen in the 1 H-NMR.
O
Examples for E :
O
soft E
E
R I
OH
hard E
Vinylogous Behaviour:
O
OH
behaves like a
carboxlic acid
pK a = 9-10
O
OH
O
OH
E
O
,
EtO Cl
Synthesis by Piers et al Can. J. Chem. 1982, 60, 1256-1263
O O
O
R
O
O
This one also
O
O
O
OH
H
O O