Chemistry Reference
In-Depth Information
Tab. 4.51.
Oxidation of alcohols using the triphosgene/DMSO system
a
[1362].
Entry
Substrate
Product
b
Yield
(%)
c
HH
HH
Et
Et
CHO
OH
a
82
1886
N
N
PMP
PMP
O
O
O
HH
HH
HH
i-Pr
i-Pr
CHO
OH
b
80
N
N
N
PMP
PMP
O
O
O
HH
HH
PhO
PMP
PhO
PMP
H
O
c
95
N
N
Ph
Ph
O
O
OH
OH
O
H
H
H
H
Ph
Ph
d
79
N
N
PMP
PMP
O
O
HH
HH
Et
Et
CHO
OH
e
83
N
N
O
O
OSiMe
2
t
Bu
OSiMe
2
t
Bu
f
83
OH
H
3
C
H
3
C
CHO
H
H
OSi
i
Pr
3
OSi
i
Pr
3
g
84
OH
H
3
C
H
3
C
CHO
H
H
H
H
CHO
OH
h
81
N
N
O
O
Boc
Boc
a
Reactions conducted on a 10-mmol scale, except for entry a and b;
b
All compounds are racemic except entries f, g, and h;
c
Yield of pure isolated product checked by GLC/EIMS.
Table 4.52 compares the results obtained for the oxidation of alcohols with the tri-
phosgene/DMSO reagent with those obtained using the traditional Swern method
(oxalyl chloride/DMSO) [1363].
Typical procedure. 2-(p-Anisyl)ethanal 1889 (Table 4.52) with triphosgene [1363]:
To
a solution of triphosgene (0.29 g, 0.97 mmol) in dry dichloromethane (40 mL) at
