Parikh-Doering Oxidation
Mechanism of the Parikh-Doering Oxidation
Sample reactions
Et3N, Pyr.SO3
DMSO
RT, 30 min, 85%
Et3N, Pyr.SO3
DMSO
RT, 10 min, 97%
DMSO, Et3N, Pyr.SO3
CH2Cl2
0 °C, 90 min, 94% (2 steps)
DMSO, Et3N, Pyr.SO3
CH2Cl2
0 °C, 90 min, 100%
DMSO, Et3N, Pyr.SO3
CH2Cl2
0 °C, 2 h, 78%
DMSO, Et3N, Pyr.SO3
CH2Cl2
5 °C to RT, , 75%
DMSO, Et3N, Pyr.SO3
CH2Cl2
0 °C, 30 min, 90%
DMSO, Et3N, Pyr.SO3
CH2Cl2
0 °C, 30 min, 93%
Et3N, Pyr.SO3
DMSO
RT, 4 h, 70%
Et3N, Pyr.SO3
DMSO
RT, 60 min
DMSO, i-Pr2NEt, Pyr.SO3
CH2Cl2
0 °C, 30 min
DMSO, i-Pr2NEt, Pyr.SO3
CH2Cl2
0 °C, 2 h
Et3N, Pyr.SO3
DMSO
RT, , 80%
Et3N, Pyr.SO3
DMSO
RT, 30 min
DMSO, Et3N, Pyr.SO3
CH2Cl2
0 °C to RT, 16.5 h, 81% (2 steps)
Et3N, Pyr.SO3
DMSO
RT, 20 min, 81%
DMSO, i-Pr2NEt, Pyr.SO3
CH2Cl2
0 °C, 20 min
"The crude aldehyde was used in the next step (see part 3)"
DMSO, i-Pr2NEt, Pyr.SO3
CH2Cl2
0 °C, 20 min, 91%
DMSO, i-Pr2NEt, Pyr.SO3
CH2Cl2
0 °C, 25 min
DMSO, i-Pr2NEt, Pyr.SO3
CH2Cl2
0 °C, 15 min, 66%
"93:07 d.r."
DMSO, Et3N, Pyr.SO3
CH2Cl2
-5 °C, 90 min, 99%
DMSO, Et3N, Pyr.SO3
CH2Cl2
RT, ON, 25% (2 steps)
"Also isolated was 26% of the C2 epimer which was epimerized to the desired isomer (Et3N/DCM) in 80% yield."
DMSO, Et3N, Pyr.SO3
CH2Cl2
0 °C, 65 min, 46%