Wolf rearrangement

1. It involves migration of a substituent to
an uncharged, electron deficient, carbon
atom called carbene
That is a molecule containing a neutral
carbon atom with two unshared valence
electrons. The general formula is RR'C:

2. The term "carbene" may also refers to the
compound H
2C:, also called methylene
Carbenes are classified as either singlets or triplets
depending upon their electronic structure
Most of the carbenes are very short lived, although
persistent carbenes are known

3. In this rearrangement α-diazoketones
lose nitrogen to form highly reactive
ketenes

4. R C
O
CHN
2
R
C
O
CHNN
+
**
-N
2
R
C
O
CH
**
R
C
O
C
H

5. - Synthesis of analogues of carboxylic
acids
- Synthesis of acid amides from
carboxylic acids
- Synthesis of esters from carboxylic
acids

6. RC
O
OH
SOCl
2
RC
O
Cl
CH
2N
2
R
C
O
CHNN
+
**
-N
2
R
C
O
CH
**
R
C
O
C
H
H
2
O
R-CH
2-C-OH
O
R-CH
2-C-NH
2
O
R-CH
2-C-O CH
3
O
N
H
3
C
H
3
O
H
Diazomethane