Mechanistic studies involving organolithium intermediates

The mechanisms of two reactions involving organolithium intermediates were studied. Several conditions were examined to determine the mechanism of the reaction of Ph Li with E-cinnamaldehyde and the carbonylation of o-anisyl lithium. The effect of radical scavengers and the isolation of some stable derivatives intermediates suggest a mechanism initiated by electron transfer giving a radical anion-radical cation pair in the first step. Further reaction within the solvent cage leads to a transient intermediate which subsequently rearrangements gives other intermediates that allow the conversion to the different products. On the other hand, the reaction showed an interesting application in organic synthesis. Reactions with a wide range of electrophiles gave substituted products with high diastero selectivity and good yields. (author)