Crystal structure and Hirshfeld surface analysis of 2-picolyllithium·3thf.

In the title compound, (2-methyl-idene-1,2-di-hydro-pyridinium-κ)tris-(tetra-hydro-furan-κ)lithium, [Li(CHN)(CHO)], the lithium ion adopts a distorted LiNO tetra-hedral coordination geometry and the 2-picolyl anion adopts its enamido form with the lithium ion lying close to the plane of the pyridine ring. A methyl-ene group of one of the thf ligands is disordered over two orientations. In the crystal, a weak C-H⋯O inter-action generates inversion dimers.

Tuning Reactivities of tert-Butyllithium by the Addition of Stoichiometric Amounts of Tetrahydrofuran.

In alkyllithium chemistry the highest reactivity has historically been linked to the smallest degree of aggregation possible. Since tert-butyllithium is known to form a monomer in tetrahydrofuran solution, using just stoichiometric amounts of the lewis base to selectively form a dimeric species seemed irrational. In this study, we showed a considerable increase of the reactivity of t-BuLi when using stoichiometric amounts of THF in the non-polar solvent n-pentane in order to enable the deprotonation of simple methyl silanes and other low C-H-acidic substrates.