Jones Oxidation

Schematic representation of the Jones Oxidation.

Mechanism of the Jones Oxidation

Mechanism of the Jones Oxidation

Original publication	J. Chem. Soc.. 1946, 0, 39. Org. Lett.. 2007, 9, 1951.
Review	Comp. Org. Syn.. 1991, 7, 251.

Sample reactions

intermediate structure

CrO3

AcOH, H2O

0 to 50 °C, ON, 30% (2 steps)

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

-5 °C, , 97%

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

5 °C, 2.5 h, 92%

intermediate structure

intermediate structure

CrO3

AcOH, H2O

RT, 10 h, 60% (2 steps)

intermediate structure

intermediate structure

CrO3, HIO4

H2O, MeCN

0 °C, 30 min, 78%

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone

RT, 45 min, 75%

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone

RT, 30 min, 95%

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone

92% (2 steps)

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone

54% (2 steps)

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone

89%

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O, MeOH

0 °C, 30 min, 16%

intermediate structure

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

RT, 2.5 h, 97%

intermediate structure

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

98%

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

0 °C to RT, 8.5 h, 98%

intermediate structure

intermediate structure

CrO3, H2SO4

H2O

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

RT, 30 min, 49% (2 steps)

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

93% (2 steps)

intermediate structure

intermediate structure

H2SO4, Na2Cr2O7

Acetone, H2O

80%

intermediate structure

intermediate structure

CrO3, H2SO4, Celite

Acetone, H2O

0 °C, 30 min

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

0 °C

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

95%

intermediate structure

intermediate structure

H2SO4, Na2Cr2O7

Et2O, H2O

RT, 2.5 h, 72% (3 steps)

"Mixture of positional isomers."

intermediate structure

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

RT, , 28%

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

0 °C, , 47% (2 steps)

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

0 °C to RT, 100 min, 92%

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

RT, 12 h, 94%

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

0 °C, 60 min, 97%

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

RT, 45 min, 95%

intermediate structure

intermediate structure

CrO3, H2SO4

CH2Cl2, H2O

0 °C, 60 min, 68%

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

-30 °C, 5 h, 61%

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

0 °C, 4 h

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

70%

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

-10 °C

"The starting material was synthesized in part 1"

intermediate structure

intermediate structure

AcOH, CrO3

H2O

RT, 22 h

intermediate structure

intermediate structure

CrO3

AcOH, H2O

RT, 24 h, 32% (4 steps)

"First relay molecule."

intermediate structure

intermediate structure

CrO3

AcOH

RT, 24 h, 84%

"See: Z. Physiol. Chem. 1935, 234, 218."

intermediate structure

intermediate structure

CrO3

AcOH

RT, 24 h, 86% (2 steps)

"See: Helv. Chim. Acta 1946, 29, 468."

intermediate structure

intermediate structure

CrO3, H2SO4

Acetone, H2O

0 °C, , 86%

intermediate structure