Swern Oxidation

Schematic representation of the Swern Oxidation.

Mechanism of the Swern Oxidation

Mechanism of the Swern Oxidation

Original publication	Tetrahedron. 1978, 34, 1651. Tetrahedron: Asymmetry. 2007, 18, 2021.
Reviews	Comp. Org. Syn.. 1991, 7, 291. Org. React.. 1990, 39, 297. Synthesis. 1981, 0, 165. Synthesis. 1990, 0, 857.

Sample reactions

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 90 min, 85%

intermediate structure

intermediate structure

DMSO, i-Pr2NEt, (CF3CO)2O

CH2Cl2

-60 to 0 °C, , 85% (2 steps)

intermediate structure

intermediate structure

DMSO, i-Pr2NEt, (CF3CO)2O

CH2Cl2

-60 to 0 °C, , 76% (2 steps)

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 6 d, 91% (2 steps)

intermediate structure

intermediate structure

Phosgene, DMSO, Et3N

CH2Cl2

-78 °C to RT, 30 min, 83% (2 steps)

intermediate structure

intermediate structure

(COCl)2, DMSO, i-Pr2NEt

CH2Cl2

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 to 0 °C, 90 min, 92% (3 steps)

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 35 min

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 30 min, 95%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 10 h

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 to 0 °C, ON, 92%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 75 min, 97%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 75 min, 94% (2 steps)

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 45 min, 97%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 75 min, 95%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C, 70 min, 98%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C, , 96%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-70 °C to RT, 40 min, 99%

intermediate structure

intermediate structure

DBU, DMSO, (CF3CO)2O

CH2Cl2

-78 °C to RT, 21 h

intermediate structure

intermediate structure

DMSO, Et3N, (CF3CO)2O

CH2Cl2

-78 °C to RT, 50 min, 57-68% (3 steps)

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 2.5 h, 93%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C

intermediate structure

intermediate structure

(COCl)2, Et3N

DMSO

-78 °C to RT, 2.5 h, 83%

intermediate structure

intermediate structure

(COCl)2, DMSO, i-Pr2NEt

CH2Cl2

-78 °C to RT, 40 min

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 5.5 h, 100%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 2 h

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 2 h

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C

intermediate structure

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 22 min, 62% (2 steps)

"Also isolated was the C4-ketone (10 % yield)."

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 to 0 °C, 105 min, 91%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 2 h, 98%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 85 min, 87%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 to 0 °C, 90 min

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C, , 91%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N, Ph3P=CHCO2Et

CH2Cl2

-65 °C to RT, 5 h

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

THF

-78 °C to RT, 23 min, 93%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-60 °C to RT, 50 min, 80%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT

intermediate structure

intermediate structure

DMSO, Et3N, (CF3CO)2O

CH2Cl2

-78 °C to RT, 100 mnin, 85%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 80 min

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 to 0 °C, 2.5 h, 98%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C, 80 min, 100%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

99%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

95%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 to 4 °C, 13 h

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 70 min, 95%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 20 min, 98%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 1 h

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C, , 97%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 to -30 °C, 5 h

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 to 0 °C, 2.5 h

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N, TsNHNH2

CH2Cl2

-78 °C to RT, 35 min

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 110 min, 90%

intermediate structure

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 50 min, 97%

intermediate structure