Anion translocation in organolithiums: A mechanism for the lithiation and cyclisation of tertiary naphthamides

Deuterium labelling shows that an intramolecular proton transfer ('anion translocation') is a key step in the mechanism leading to an α-lithiated tertiary naphthamide and thence to the products of anionic cyclisation. The kinetic isotope effect means that proton transfer from the ortho position can become the sole mechanism for α-lithiation, though for undeuterated amides a parallel mechanism also operates in which lithiation occurs directly at the position α to nitrogen.