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
CF3CO2H, MeNO2
intermediate structure
intermediate structure
Ph3P
CF3CO2H, CH2Cl2
intermediate structure
intermediate structure intermediate structure
NaHCO3
CH2Cl2
Reflux
intermediate structure