Pummerer Rearrangement

Schematic representation of the Pummerer Rearrangement.
Mechanism of the Pummerer Rearrangement
Mechanism of the Pummerer Rearrangement
Original publication
Ber. Dtsch. Chem. Ges.. 1909, 42, 2282.
Reviews
Angew. Chem. Int. Ed.. 2010, 49, 5832. Chem. Rev.. 2004, 104, 2401. Comp. Org. Syn.. 1991, 6, 937. Curr. Org. Chem.. 2000, 4, 175. Org. React.. 1991, 40, 157. Synlett. 2002, 0, 851. Synthesis. 1997, 0, 1353.
Sample reactions
info
intermediate structure
2,6-Lutidine, NaOAc, (CF3CO)2O
Ac2O
RT, 60 min
intermediate structure
info
intermediate structure
(CF3CO)2O, 2,6-Di-tert-butyl-4-methylpyridine
CH2Cl2
RT, 3 h
intermediate structure
info
intermediate structure
(CF3CO)2O
CH2Cl2
0 °C to RT, 2.5 d, 95%
intermediate structure
info
intermediate structure
Ac2O, DMSO
RT, 24 h, 99%
intermediate structure