Curtius Rearrangement

Schematic representation of the Curtius Rearrangement.
Mechanism of the Curtius Rearrangement
Mechanism of the Curtius Rearrangement
Sample reactions
intermediate structure
(PhO)2P(O)N3, Et3N
t-BuOH
Reflux, 17 h, 54%
intermediate structure
intermediate structure
(PhO)2P(O)N3, (4-MeOPh)CH2OH
PhMe, Et3N
Reflux, 12 h, 72%
intermediate structure
intermediate structure
PhH
90 °C
intermediate structure
intermediate structure
NaN3
PhMe
intermediate structure
intermediate structure
(PhO)2P(O)N3, Et3N
CH2Cl2
40 °C, 16 h, 78%
intermediate structure
intermediate structure
Ac2O
AcOH
RT, 49 h
intermediate structure
intermediate structure
(PhO)2P(O)N3, Et3N
PhH
RT to Reflux, 7.5 h, 84%
intermediate structure
intermediate structure
(PhO)2P(O)N3, Et3N
THF
Reflux, 15 h
intermediate structure
intermediate structure
ClCO2Et, Et3N, NaN3
PhMe
Reflux
intermediate structure