07/12/2012 - Organolithium Ether Cleavage

There comes a point in a compound's life when there is a question of whether there is an easier way to make it, and in 1930 Karl Ziegler questioned this with organolithium compounds.  Not only did he find more simpler ways of preparing such organolithium compounds but he developed many applications for the use of the light metal.  The largest application of these compounds is in organic chemistry as organolithium reagents, used in creating those precious carbon-carbon bonds. But one of the first applications that Ziegler developed was the ability of Lithium to cleave an ether bond, demonstrated in the following reaction:

PhCH₂OMe + 2Li → PhCH₂Li + MeOLi