Dess-Martin Oxidation

Schematic representation of the Dess-Martin Oxidation.

Mechanism of the Dess-Martin Oxidation

Mechanism of the Dess-Martin Oxidation

Original publication	J. Org. Chem.. 1983, 48, 4155. Chem. Eur. J.. 2010, 16, 4091.
Review

Sample reactions

intermediate structure

Dess-Martin Periodinane

CH2Cl2

0 °C to RT, 3 h, 85% (2 steps)

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 3 h, 90%

intermediate structure

intermediate structure

Dess-Martin Periodinane, NaHCO3

CH2Cl2

0 °C, 90 min

intermediate structure

intermediate structure

Dess-Martin Periodinane, NaHCO3

CH2Cl2

0 °C, 20 min

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 3.5 h

intermediate structure

intermediate structure

Dess-Martin Periodinane, Pyr

CH2Cl2

RT, 8 h, 94%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 2 h

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 2 h

intermediate structure

intermediate structure

Dess-Martin Periodinane, Et3N, NaHCO3, H2CN+Me2 I-

CH2Cl2

RT, ON, 97%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, ON, 77%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 60 min, 92%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 60 min

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

-40 to 10 °C, 90 min, 74%

intermediate structure

intermediate structure

Dess-Martin Periodinane, NaHCO3

CH2Cl2

0 °C to RT, 6 h, 89%

intermediate structure

intermediate structure

Dess-Martin Periodinane, NaHCO3

CH2Cl2

0 to 25 °C, 4 h, 96%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

4 °C to RT, 3 h, 88%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CHCl3

RT, 60 min, 96%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 2 h

intermediate structure

intermediate structure

Dess-Martin Periodinane, SeO2

Dioxane

75 °C to RT, 4.5 h, 58%

intermediate structure

intermediate structure

Dess-Martin Periodinane, NaHCO3

CH2Cl2

0 °C, 60 min, 59% (2 steps)

"The yield was 73 % brsm."

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

0 °C to RT, 2 h, 96%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 60 min, 90%

intermediate structure

intermediate structure

Dess-Martin Periodinane, NaHCO3

CH2Cl2

RT, 2 h, 80% (2 steps)

intermediate structure

intermediate structure

Dess-Martin Periodinane, NaHCO3

CH2Cl2

RT, 2 h, 87% (2 steps)

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

4 °C to RT, 25 min, 90%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

0 °C to RT, 3.5 h

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

0 °C, 4.5 h, 90%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

0 °C to RT, 35 min, 69% (3 steps)

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

0 °C, 60 min, 91%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

0 °C to RT, 10 h, 84% (2 steps)

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 3 min, 90%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2, Pyr

RT, 5 min, 90%

intermediate structure

intermediate structure

Dess-Martin Periodinane, Pyr

CH2Cl2

13 °C to RT, 25 min, 90%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 30 min, 91%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2, H2O

intermediate structure

intermediate structure

Dess-Martin Periodinane, NaHCO3

CH2Cl2

RT, 2.5 h, 77% (3 steps)

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 4 h, 80% (2 steps)

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 2 h

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 30 min, 95%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 20 min, 86% (2 steps)

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 2 h, 83%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 1 min, 83%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 20 min, 72%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 30 min, 60% (5 steps)

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 90 min

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 10 min, 100%

intermediate structure

intermediate structure

Dess-Martin Periodinane

CH2Cl2

92% (2 steps)

intermediate structure

intermediate structure

Dess-Martin Periodinane, Pyr

CH2Cl2

0 °C to RT, 2.5 h, 92%

intermediate structure