112197-01-0Relevant academic research and scientific papers
Lithiation of 2-chloro- and 2-methoxypyridine with lithium dialkylamides: Initial ortho-direction or subsequent lithium ortho-stabilization?
Gros, Philippe,Choppin, Sabine,Fort, Yves
, p. 2243 - 2247 (2003)
The lithiation pathway of 2-chloro and 2-methoxypyridine with LDA and LTMP has been investigated using deuterated probes. The availability of both H-6 and H-3 protons on the pyridine nucleus was found to be critical to ensure complete C-3 lithiation. We thus concluded that the C-3 lithiation was not a straightforward process. A mechanism involving precomplexation of lithium dialkylamides near the H-6 proton and formation of a 3,6-dilithio pyridine intermediate is proposed.
