Grob Fragmentation

Schematic representation of the Grob Fragmentation.
Mechanism of the Grob Fragmentation
Mechanism of the Grob Fragmentation
Sample reactions
intermediate structure
Dimsyl lithium
DMSO
RT, 30 min
intermediate structure
intermediate structure
t-BuOOH, Ti(Oi-Pr)4
CH2Cl2
0 °C to Reflux, 9.5 h
intermediate structure
intermediate structure
DABCO, TIPSOTf, 2,6-Lutidine
CH2Cl2
-78 °C to Reflux, 14 h, 85% (2 steps)
intermediate structure
intermediate structure
KOt-Bu
t-BuOH
35 °C, 60 min, 100%
intermediate structure
intermediate structure
KOH
H2O
intermediate structure
intermediate structure
i-Bu2AlH
PhMe
Reflux, 72 h, 71%
intermediate structure