Jones Oxidation

Mechanism of the Jones Oxidation

Original publication | |
---|---|
Review |
Sample reactions

CrO3
AcOH, H2O
0 to 50 °C, ON, 30% (2 steps)


CrO3, H2SO4
Acetone, H2O
-5 °C, , 97%


CrO3, H2SO4
Acetone, H2O
5 °C, 2.5 h, 92%


CrO3
AcOH, H2O
RT, 10 h, 60% (2 steps)


CrO3, HIO4
H2O, MeCN
0 °C, 30 min, 78%


CrO3, H2SO4
Acetone
RT, 45 min, 75%


CrO3, H2SO4
Acetone
RT, 30 min, 95%


CrO3, H2SO4
Acetone
92% (2 steps)


CrO3, H2SO4
Acetone
54% (2 steps)


CrO3, H2SO4
Acetone
89%


CrO3, H2SO4
Acetone, H2O


CrO3, H2SO4
Acetone, H2O, MeOH
0 °C, 30 min, 16%



CrO3, H2SO4
Acetone, H2O
RT, 2.5 h, 97%



CrO3, H2SO4
Acetone, H2O
98%


CrO3, H2SO4
Acetone, H2O
0 °C to RT, 8.5 h, 98%


CrO3, H2SO4
H2O


CrO3, H2SO4
Acetone, H2O
RT, 30 min, 49% (2 steps)


CrO3, H2SO4
Acetone, H2O
93% (2 steps)


H2SO4, Na2Cr2O7
Acetone, H2O
80%


CrO3, H2SO4, Celite
Acetone, H2O
0 °C, 30 min


CrO3, H2SO4
Acetone, H2O
0 °C


CrO3, H2SO4
Acetone, H2O
95%


H2SO4, Na2Cr2O7
Et2O, H2O
RT, 2.5 h, 72% (3 steps)
"Mixture of positional isomers."



CrO3, H2SO4
Acetone, H2O
RT, , 28%


CrO3, H2SO4
Acetone, H2O
0 °C, , 47% (2 steps)


CrO3, H2SO4
Acetone, H2O
0 °C to RT, 100 min, 92%


CrO3, H2SO4
Acetone, H2O
RT, 12 h, 94%


CrO3, H2SO4
Acetone, H2O
0 °C, 60 min, 97%


CrO3, H2SO4
Acetone, H2O
RT, 45 min, 95%


CrO3, H2SO4
CH2Cl2, H2O
0 °C, 60 min, 68%


CrO3, H2SO4
Acetone, H2O
-30 °C, 5 h, 61%


CrO3, H2SO4
Acetone, H2O
0 °C, 4 h


CrO3, H2SO4
Acetone, H2O
70%


CrO3, H2SO4
Acetone, H2O
-10 °C
"The starting material was synthesized in part 1"


AcOH, CrO3
H2O
RT, 22 h


CrO3
AcOH, H2O
RT, 24 h, 32% (4 steps)
"First relay molecule."


CrO3
AcOH
RT, 24 h, 84%
"See: Z. Physiol. Chem. 1935, 234, 218."


CrO3
AcOH
RT, 24 h, 86% (2 steps)
"See: Helv. Chim. Acta 1946, 29, 468."


CrO3, H2SO4
Acetone, H2O
0 °C, , 86%
