Jasmone 1 - ChemistforChrist

Synthesis of JASMONE
Additional information:
Reaction of Perkow: JACS 1955, 77, 2871
Perkow:
O
O
Cl Cl
O
Cl Cl
Arbusow:
EtO
EtO P
EtO
P(OEt) 3
∆
P(OEt) 3
R Br
Cl
Cl
O
O
EtO
EtO P
O
P(OEt) 2
P(OEt) 3
Et
Br
HWE-Reagent (HWE = Horner-Wadsworth-Emmons)
Synthesis by McMurry
JOCS 1973, 38, 4367-4373
JACS 1971, 93 5309-5311
New approach to create the 1,4 diketone
2
3
O
1
4
O
O
+
R
O
R
R
S S
NO 2
The conditions of the Nef-reaction are rather harsh:
O O
N
H
OH
NaOH
O O
N
H 2SO 4
conc.
reflux
R
R
Cl
Cl
HO OH
N
O
O
O
EtO
EtO P
O
P(OEt) 2
P(OEt) 2
Et
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O
H 2O
R
+ EtBr
S S
E
E
NO 2
R
R
O
Hg(II)
1. NaOH
2. H 2SO 4
Nef-reaction
Et
Et
O
O
R
R