Remote-controlled nucleophilicity III: A valuable model to explain and predict the observed regioselectivity of the electrophilic attack on substituted 4-methylpyridine anions

In a comparative study, the stability of lithiated methylpyridine and the reactivity of side chain functionalized 4-methylypridines were investigated. In contrast to gas phase calculations, the observed N-coordination of the lithium to 4-methylpyridine anions is shown to be a solvent effect. Furthermore, lithiated methylpyridines are predicted to be dimeric in THF. The regioselectivity of the picoline anion alkylation was subject to an in-depth...