Curtius Rearrangement

Schematic representation of the Curtius Rearrangement.
Mechanism of the Curtius Rearrangement
Mechanism of the Curtius Rearrangement
Original publication
Ber. Dtsch. Chem. Ges.. 1890, 23, 3023. Tetrahedron. 2008, 64, 5531.
Reviews
Chem. Rev.. 1988, 88, 297. Org. React.. 1946, 3, 337.
Sample reactions
info
intermediate structure
(PhO)2P(O)N3, Et3N
t-BuOH
Reflux, 17 h, 54%
intermediate structure
info
intermediate structure
(PhO)2P(O)N3, (4-MeOPh)CH2OH
Et3N, PhMe
Reflux, 12 h, 72%
intermediate structure
info
intermediate structure
PhH
90 °C
intermediate structure
info
intermediate structure
NaN3
PhMe
intermediate structure
info
intermediate structure
(PhO)2P(O)N3, Et3N
CH2Cl2
40 °C, 16 h, 78%
intermediate structure
info
intermediate structure
Ac2O
AcOH
RT, 49 h
intermediate structure
info
intermediate structure
(PhO)2P(O)N3, Et3N
PhH
RT to Reflux, 7.5 h, 84%
intermediate structure
info
intermediate structure
(PhO)2P(O)N3, Et3N
THF
Reflux, 15 h
intermediate structure
info
intermediate structure
ClCO2Et, Et3N, NaN3
PhMe
Reflux
intermediate structure