A Chemical, Spectroscopic, and Theoretical Assessment of the Lewis Acidity of LiClO4 in Diethyl Ether

Article abstract of DOI:10.1021/jo00063a037

Moderate diastereoselectivity is observed in the reaction of cyclopentadiene with dimethyl maleate and optically active dimenthyl fumarate in LiClO4/diethyl ether.Moderate regioselectivity is also seen in the reaction of isoprene and methyl acrylate in the same medium.NMR experiments and MNDO calculations, in conjunction with published work on Li(1+) in the gas phase, demonstrate that the strong, intrinsic Lewis acidity of Li⁺ is moderated in ether by complexation to the solvent and the counterion.