Lithiation of lithium (2-pyridylmethyl)(tert-butyldimethylsilyl)amide – synthesis and structural characterization of a 1,2-dilithiated (2-pyridylmethyl)(tert-butyldimethylsilyl)amine

The lithiation of (2-pyridylmethyl)(tert-butyldimethylsilyl)amine in THF yields semi(tetrahydrofuran)lithium (2-pyridylmethyl)(tert-butyldimethylsilyl)amide (1), which reacts with another equivalent of methyllithium to the octameric dilithium (2-pyridylmethanidyl)(tert-butyldimethylsilyl)amide (2). The molecular structure of 2 indicates that the negative charges are delocalized within the pyridyl moiety with a localization mainly on the nitrogen atoms.