Swern Oxidation
Mechanism of the Swern Oxidation
Sample reactions
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 90 min, 85%
DMSO, i-Pr2NEt, (CF3CO)2O
CH2Cl2
-60 to 0 °C, , 85% (2 steps)
DMSO, i-Pr2NEt, (CF3CO)2O
CH2Cl2
-60 to 0 °C, , 76% (2 steps)
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 6 d, 91% (2 steps)
Phosgene, DMSO, Et3N
CH2Cl2
-78 °C to RT, 30 min, 83% (2 steps)
(COCl)2, DMSO, i-Pr2NEt
CH2Cl2
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, 90 min, 92% (3 steps)
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 35 min
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 30 min, 95%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 10 h
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, ON, 92%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 75 min, 97%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 75 min, 94% (2 steps)
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 45 min, 97%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 75 min, 95%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C, 70 min, 98%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C, , 96%
(COCl)2, DMSO, Et3N
CH2Cl2
-70 °C to RT, 40 min, 99%
DBU, DMSO, (CF3CO)2O
CH2Cl2
-78 °C to RT, 21 h
DMSO, Et3N, (CF3CO)2O
CH2Cl2
-78 °C to RT, 50 min, 57-68% (3 steps)
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 2.5 h, 93%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C
(COCl)2, Et3N
DMSO
-78 °C to RT, 2.5 h, 83%
(COCl)2, DMSO, i-Pr2NEt
CH2Cl2
-78 °C to RT, 40 min
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 5.5 h, 100%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 2 h
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 2 h
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 22 min, 62% (2 steps)
"Also isolated was the C4-ketone (10 % yield)."
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, 105 min, 91%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 2 h, 98%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 85 min, 87%
(COCl)2, DMSO, Et3N
CH2Cl2
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, 90 min
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C, , 91%
(COCl)2, DMSO, Et3N, Ph3P=CHCO2Et
CH2Cl2
-65 °C to RT, 5 h
(COCl)2, DMSO, Et3N
CH2Cl2
(COCl)2, DMSO, Et3N
THF
-78 °C to RT, 23 min, 93%
(COCl)2, DMSO, Et3N
CH2Cl2
-60 °C to RT, 50 min, 80%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT
DMSO, Et3N, (CF3CO)2O
CH2Cl2
-78 °C to RT, 100 mnin, 85%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 80 min
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, 2.5 h, 98%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C, 80 min, 100%
(COCl)2, DMSO, Et3N
99%
(COCl)2, DMSO, Et3N
95%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 4 °C, 13 h
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 70 min, 95%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 20 min, 98%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 1 h
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C, , 97%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to -30 °C, 5 h
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, 2.5 h
(COCl)2, DMSO, Et3N, TsNHNH2
CH2Cl2
-78 °C to RT, 35 min
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 110 min, 90%
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 50 min, 97%