Wolff-Kishner Reduction

Schematic representation of the Wolff-Kishner Reduction.
Mechanism of the Wolff-Kishner Reduction
Mechanism of the Wolff-Kishner Reduction
Sample reactions
intermediate structure
NH2NH2, KOH
Ethylene Glycol
80%
intermediate structure
intermediate structure
NH2NH2.H2O, NaOH
Triethylene glycol
Reflux, 2 h, 63-83 &
intermediate structure
intermediate structure
NH2NH2, KOH
Ethylene Glycol
Reflux, , 82%
intermediate structure
intermediate structure
NH2NH2, K2CO3
Diethylene glycol
260 °C, 19 h, 63% (2 steps)
intermediate structure
intermediate structure
Na, NH2NH2
Ethylene Glycol
190-195 °C, 16 h, 100%
intermediate structure
intermediate structure
NH2NH2.H2O, K2CO3
Diethylene glycol
150 to 200 °C, 7 h, 72%
intermediate structure
intermediate structure
NH2NH2.H2O, K2CO3
Diethylene glycol
190 °C, , 73%
intermediate structure
intermediate structure
NH2NH2, KOH
Diethylene glycol
155 °C, 60 min, 92%
intermediate structure
intermediate structure
NH2NH2.H2O, KOH
Diethylene glycol
182 °C, 2.5 d, 90%
intermediate structure