Jasmone 1 - ChemistforChrist

Synthesis of JASMONE
O
O
O
O
R 1
R 1
1
2
O
O
O
O
R 1
R 1
R 2
R 2
S S +
Synthesis by S. Mann Synth. Comm. 1985, 15, 1147-1151
O
O
O N
O O Li
Solution: Hydrazone
O H 2N NMe 2
O
O
O
R 2
made out of:
O
+
N
H
N NMe 2
n-Bu Li
Cl
O
R 1
XMg
O
More resources available at
www.chemistforchrist.de
+
Nu
Br
R 2
O O R2
O O R2
Br R 2
Enamine is a too weak nucleophile.
O
To weak as a nucleophile?!
N NMe 2
Li
O
R 2
O O R2
very strong nucleophile
(charge is not delocalized)