Fritsch-Buttenberg-Wiechell Rearrangement

Mechanism of the Fritsch-Buttenberg-Wiechell Rearrangement

Original publication	Liebigs Ann.. 1894, 279, 319. Liebigs Ann.. 1894, 279, 324. Liebigs Ann.. 1894, 279, 337.
Reviews	Chem. Commun.. 2010, 46, 3235. Chem. Rev.. 1978, 78, 383. Chem. Rev.. 2004, 104, 3795.

Sample reactions

(CH2O)n, n-BuLi

THF

-78 °C to RT, 2 h, 91%

MeLi.LiBr

THF

-78 to -20 °C, 3 h, 97% (α), 93 % (β)

"The epimers are carried out separately."

n-BuLi, TMSCHN2

-78 to 0 °C, 3.5 h, 83%