Prilezhaev Reaction

Mechanism of the Prilezhaev Reaction

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Reviews |
Sample reactions

AcOOH, NaOAc
AcOH, H2O
RT to 80 °C, 16 h, 85% (2 steps)


AcOOH, Na2HPO4
DCE
4 °C, 15 h



AcOOH, Na2HPO4
DCE
RT



mCPBA
CH2Cl2
RT, 2 h


mCPBA
CH2Cl2
RT, 2 h


mCPBA
CHCl3
80% (2 steps)


mCPBA, NaHCO3
CH2Cl2
RT, 11 h, 80%


mCPBA, NaHCO3
CH2Cl2
RT, 10.5 h, 45%


mCPBA, Na2CO3
CH2Cl2
-78 to -15 °C, 14 h


mCPBA
CH2Cl2
10 °C to RT, , 89%
"Mixture of isomers."


mCPBA
CH2Cl2
74%


mCPBA, NaHCO3
CH2Cl2
RT, 15 h, 81%


Camphorsulfonic acid
CH2Cl2
0 °C, , 60%


mCPBA
CH2Cl2
0 °C, 2 h, 92%


mCPBA, NaHCO3
CH2Cl2
-20 °C, 30 min


mCPBA
CHCl3
0 °C to RT, ON, 100%


AcOOH, NaOAc
AcOH, CH2Cl2
92%


mCPBA, NaOAc
CH2Cl2
RT, 24 h


mCPBA, NaHCO3
CH2Cl2
80%


mCPBA
DCE
40 °C, 24 h, 84%


mCPBA
CH2Cl2
RT, 30 min, 98%


NaHCO3, MMPP
Sealed tube
MeOH
110 °C, 7 d, 22% (α), 65 % (β)
"The yield were 67% (α) and 93 % (β) brsm."


mCPBA
CH2Cl2
0 °C to RT, 16 h, 85%



mCPBA
CH2Cl2, Buffer (pH = 6.5)
RT, 2 h


AcOOH, Na2CO3
CH2Cl2
RT, 24 h, 68%


mCPBA, Na3PO4
CH2Cl2, H2O
RT, 24 h, 73%


mCPBA, NaHCO3
CH2Cl2
RT, 72 h, 86%


mCPBA, NaOAc
CH2Cl2
-20 to 0 °C, 90 min
