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 H2C:, 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 CHN2
O
R
C CH N N
** +
O -N2
R R
C C C CH
**
H
O O
5. - Synthesis of analogues of carboxylic
acids
- Synthesis of acid amides from
carboxylic acids
- Synthesis of esters from carboxylic
acids
6. SOCl2
R C OH R C Cl Diazomethane
O O CH2N2
R
C CH N N
** +
O -N2
R R
C C C CH
**
H
O O
CH OH
NH
H2O
3
3
O
O
O R-CH2-C-NH2
R-CH2-C-OH
R-CH2-C-O CH3