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%
