Prilezhaev Reaction

Schematic representation of the Prilezhaev Reaction.
Mechanism of the Prilezhaev Reaction
Mechanism of the Prilezhaev Reaction
Sample reactions
intermediate structure
AcOOH, NaOAc
AcOH, H2O
RT to 80 °C, 16 h, 85% (2 steps)
intermediate structure
intermediate structure
AcOOH, Na2HPO4
DCE
4 °C, 15 h
intermediate structure
intermediate structure intermediate structure
AcOOH, Na2HPO4
DCE
RT
intermediate structure intermediate structure
intermediate structure
mCPBA
CH2Cl2
RT, 2 h
intermediate structure
intermediate structure
mCPBA
CH2Cl2
RT, 2 h
intermediate structure
intermediate structure
mCPBA
CHCl3
80% (2 steps)
intermediate structure
intermediate structure
mCPBA, NaHCO3
CH2Cl2
RT, 11 h, 80%
intermediate structure
intermediate structure
mCPBA, NaHCO3
CH2Cl2
RT, 10.5 h, 45%
intermediate structure
intermediate structure
mCPBA, Na2CO3
CH2Cl2
-78 to -15 °C, 14 h
intermediate structure
intermediate structure
mCPBA
CH2Cl2
10 °C to RT, , 89%
"Mixture of isomers."
intermediate structure
intermediate structure
mCPBA
CH2Cl2
74%
intermediate structure
intermediate structure
mCPBA, NaHCO3
CH2Cl2
RT, 15 h, 81%
intermediate structure
intermediate structure
Camphorsulfonic acid
CH2Cl2
0 °C, , 60%
intermediate structure
intermediate structure
mCPBA
CH2Cl2
0 °C, 2 h, 92%
intermediate structure
intermediate structure
mCPBA, NaHCO3
CH2Cl2
-20 °C, 30 min
intermediate structure
intermediate structure
mCPBA
CHCl3
0 °C to RT, ON, 100%
intermediate structure
intermediate structure
AcOOH, NaOAc
AcOH, CH2Cl2
92%
intermediate structure
intermediate structure
mCPBA, NaOAc
CH2Cl2
RT, 24 h
intermediate structure
intermediate structure
mCPBA, NaHCO3
CH2Cl2
80%
intermediate structure
intermediate structure
mCPBA
DCE
40 °C, 24 h, 84%
intermediate structure
intermediate structure
mCPBA
CH2Cl2
RT, 30 min, 98%
intermediate structure
intermediate structure
MMPP, NaHCO3
MeOH
110 °C, 7 d, 22% (α), 65 % (β)
"The yield were 67% (α) and 93 % (β) brsm."
intermediate structure
intermediate structure
mCPBA
CH2Cl2
0 °C to RT, 16 h, 85%
intermediate structure intermediate structure
intermediate structure
mCPBA
CH2Cl2, Buffer (pH = 6.5)
RT, 2 h
intermediate structure
intermediate structure
AcOOH, Na2CO3
CH2Cl2
RT, 24 h, 68%
intermediate structure
intermediate structure
mCPBA, Na3PO4
CH2Cl2, H2O
RT, 24 h, 73%
intermediate structure
intermediate structure
mCPBA, NaHCO3
CH2Cl2
RT, 72 h, 86%
intermediate structure