Organic Synthesis
Bai,Zheng Wu
Part I Introduction
1,The development history of organic synthesis
2,The influences of organic synthesis on organic
chemistry
3,The research scope of organic synthesis
a,Find new reactions
b,Synthesize new compounds with special
functions
c,Research on natural products
Part I Introduction
4,Development trends of organic synthesis
a,Chiral synthesis
(stereo-chemistry in reactions)
b,Bio-catalytically organic synthesis
c,Utilization of special methods in organic
synthesis,
Part II Basic reactions
Oxidation reaction
1,Oxidation of side chain of aromatic
compounds
C H 3 C O O H
K M n O 4
H
+
Frequently used oxidants:
C C H 3
C H 3
H 3 C
K M n O 4
H
+
K M n O 4,K 2 C r 2 O 7,O 3 / Z n,O 3,
O 2,C H 3 C O O O H
2,Oxidation of aromatic
compounds
O 2
V 2 O 5
O
O
O
Reduction reaction
1,Hydrogenation (氢化 )
3,Oxidation of olefins
C C [ O ] C CO O+
C C [ O ] C C
O
C C [ O ] C C
O HH O
Reduction reactions
1,Hydrogenation
C C
[ H ]
[ H ]
C H C H
HH C C
HH
Stereo-chemistry of hydrogenation:
Cis-addition
2,Reduction of
-C=O to –CH-OH; NaBH4,LiAlH4,
H2/Cat.
- CN to –CH2NH2; LiAlH4,H2/Cat.
-NO2 to -NH2; LiAlH4,H2/Cat.
-CO2R to –CH2OH; Na/EtOH
Grignard reaction
Preparation of Grignard reagents:
R - X
M g
e t h e r R M g X
The ether used to prepare Grignard
reagents must be dried.
Reactions concerning Grignard
reagents
R M g X +
O
R
1
- C O - R
2
R
1
C O
2
R
2
R C H
2
C H
2
O H
R
1
- C - R
2
R
1
- C - R
R
O H
R
O H
Wittig reaction
R C H
2
X P P h
3
R - C H
2
-
+
P P h
3
X
-
+
B u L i
R - C H = P P h
3
R - C H = P P h
3
+
O
R
1
R
2
C H
2
- R
R
1
R
2
Nucelophilic reaction
O
R 1 R 2
+ C N -
R 1 R 2
H O C N
Diels-Alder reaction
H,T.,high temperature
C O 2 M e
C O 2 M e
+
H,T,
C O 2 M e
C O 2 M e