Grob Fragmentation

Schematic representation of the Grob Fragmentation.

Mechanism of the Grob Fragmentation

Mechanism of the Grob Fragmentation

Original publication	Helv. Chim. Acta. 1955, 38, 594. Tetrahedron. 2004, 60, 5013.
Reviews	Chem. Rev.. 2010, 110, 3741. Comp. Org. Syn.. 1991, 6, 1041.

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

2,6-Lutidine, TIPSOTf, DABCO

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

intermediate structure

intermediate structure

t-BuLi

Et2O, Pentane

25 - 30 °C, , 50% (2 steps)

intermediate structure

intermediate structure

HCl

H2O, MeCN

RT, 24 h, 91%

intermediate structure