TWO GROUP C-X

DISCONNECTION
 1,1-Dfunctionalized Compounds

 Two heteroatoms joined to the same carbon

atom

X HX
O +
Y HY
  Bagaimanakah menganalisis dan mensintesis
senyawa berikut?

OH
OM e 5.
NH 2
HO
1. Ph
OM e 3.
H 2N C O 2H
HO
Cl NH 2 6.
2.
O O 4. R
Cl
C O 2H O
 OM e
1. Ph
OM e

A n a l i s is

O M e 1 ,1 -d iX O
Ph C + 2 M eO H
Ph
A c e ta l H
O M e

S in te s is
M eO H O M e
O
Ph C Ph
+
H H O M e
 1,2-Difuncionalised Compounds
1. Alcohol

N u
O CO R

N u -
N u + OH =
N u OH O
Cl
 Contoh
H 2N
OH
A n a l i s is

H 2N 1 ,2 - d iX
RN H + O
O H 2

S in te s is

O H 2N
RNH 2
OH
+
H
Bagaimana mensintesis senyawa berikut
dengan 1,2-diX?
O O H
1. 2. N
N E t2

N H 2 O

O H

3. O
Ph
 1,2-Difuntionalised Compounds
2. Carbonyl Compounds

O O
O
1 ,2 - d i X
Nu - = H al
Nu + R
R R
 Contoh
O C O 2H

Cl Cl

A n a li s is

O C O 2H O H O H
C -C l
1 ,2 - d i X Cl C O 2H +

Cl Cl Cl Cl

S in t e s is

OH OH O C O 2H
C l2 1. N aO H
F e C l3 Cl C O 2H
Cl Cl Cl Cl
Bagaimana mensintesis senyawa berikut?

O
1. 2.
O R O

N E t2
O
Br

3. O
4. SH

O
 1,3-Difunctionalised Compounds
 Disconnect only at the carbonyl oxidation level

R R
Nu R Nu
-
+ =

O O
O
 Contoh
Pada analisis, CN kepanjangen

O N H 2

A n a l i s is
FG I
R O N H 2 R O CN -
R O + CN
r e d u c tio n

S in te sis

N aO M e CN H 2
O H O O N H 2

CN R h , A l2O 3
Bagaimana mensintesis senyawa berikut?

2. O
1.
O O CH 3
Cl
H O

B r
C H 2C H 3

O 4. O
3.

N H 2

O H