Eschenmoser Sulfide Contraction

Schematic representation of the Eschenmoser Sulfide Contraction.
Mechanism of the Eschenmoser Sulfide Contraction
Mechanism of the Eschenmoser Sulfide Contraction
Original publication
Review
Sample reactions
intermediate structure
P(OEt)3
Xylene(s)
125 °C, , 85% (2 steps)
intermediate structure
intermediate structure
P(CH2CH2CN)3
MeNO2, CF3CO2H
intermediate structure
intermediate structure
Ph3P
CH2Cl2, CF3CO2H
intermediate structure
intermediate structure intermediate structure
NaHCO3
CH2Cl2
Reflux
intermediate structure