| Abstract: | Several intermediates from the reactions of nitrogen heterocycles with organolithium compounds were successfully isolated and were characterized by their proton magnetic resonance (pmr) spectra. Using TMED (N,N,N',N ' -tetramethylethylenediamine) and THF ( tetra - hydrofuran) as solvents, the pmr parameters were obtained for the intermediates from the reaction of phenyllithium with the following nitrogen heterocycles: pyridine ; 4-t-butylpyridine; 3-picoline ; 3,5-lutidine; 4-phenylpyridine; quinoline; 6-methylquinoline; 7- methylquinoline; and 8-methylquinoline. The pmr spectrum of the 2-phenylpyridine-phenyllithium intermediate was also taken in THF. Also, the pmr parameters were reported for the intermediates from the reactions of t-butyllithium with pyridine, 3 -picoline , 4 --t-butylpyridine , and quinoline, respectively. In the case of the reaction with 3 -picoline , the pmr spectrum of the reaction mixture gave evidence of the existence of two isomeric intermediates resulting from 1 ,2 - and 1 ,6 -addition of the t-butyllithium to the 3 --picoline.. |
|---|