P. Gros, S. Choppin, Y. Fort
Feb 12, 2003
Citations
1
Influential Citations
24
Citations
Journal
The Journal of organic chemistry
Abstract
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.