Wolff-Kishner Reduction

Schematic representation of the Wolff-Kishner Reduction.
Mechanism of the Wolff-Kishner Reduction
Mechanism of the Wolff-Kishner Reduction
Original publication
J. Russ. Chem. Soc.. 1911, 43, 582. Liebigs Ann.. 1912, 394, 86. Tetrahedron. 2011, 67, 10203.
Review
Org. React.. 1948, 4, 378.
Sample reactions
info
intermediate structure
KOH, NH2NH2
Ethylene Glycol
80%
intermediate structure
info
intermediate structure
NaOH, NH2NH2.H2O
Triethylene glycol
Reflux, 2 h, 63-83 &
intermediate structure
info
intermediate structure
KOH, NH2NH2
Ethylene Glycol
Reflux, , 82%
intermediate structure
info
intermediate structure
K2CO3, NH2NH2
Diethylene glycol
260 °C, 19 h, 63% (2 steps)
intermediate structure
info
intermediate structure
NH2NH2, Na
Ethylene Glycol
190-195 °C, 16 h, 100%
intermediate structure
info
intermediate structure
K2CO3, NH2NH2.H2O
Diethylene glycol
150 to 200 °C, 7 h, 72%
intermediate structure
info
intermediate structure
K2CO3, NH2NH2.H2O
Diethylene glycol
190 °C, , 73%
intermediate structure
info
intermediate structure
KOH, NH2NH2
Diethylene glycol
155 °C, 60 min, 92%
intermediate structure
info
intermediate structure
KOH, NH2NH2.H2O
Sealed tube
Diethylene glycol
182 °C, 2.5 d, 90%
intermediate structure
info
intermediate structure
NaOMe, NH2NH2.H2O
MeOH
195-200 °C, 9 h, 52%
intermediate structure
info
intermediate structure
KOH, NH2NH2.H2O
Triethylene glycol
140 to 190 °C, 6 h, 40-49%
intermediate structure
info
intermediate structure
NH2NH2, Na
Diethylene glycol
RT to 227 °C, 6 h, 55%
intermediate structure
info
intermediate structure
NH2NH2, Na
Diethylene glycol
RT to 255 °C, 5.5 h, 71%
"The enantiomers were resolved with di-p-toluoyl-L-tartaric acid."
intermediate structure
info
intermediate structure
NH2NH2, Na
Ethylene Glycol
190-195 °C, 16 h, 76%
intermediate structure
info
intermediate structure
NH2NH2
EtOH
Reflux, 12 h, 90%
intermediate structure