Journal of Organic Chemistry p. 2130 - 2133 (1983)
Update date:2022-08-25
Topics:
Bassfield, Ronald L.
Houminer, Yoram
The selectivity in the LDA-promoted lithiation of 2,3,5-trimethylpyrazine was studied by using the perdeuterated substrate 1-d9.Quenching of the lithium salts of the latter with H2O gave a 1-d8 isomer mixture which was analyzed by NMR.The order of reactivity of the three CH3 groups in 1-d9 was found to be 3 > 2 > 5.The metalation studies were extended also to isomeric dimethylpyrazines.It was established that the two ortho CH3 groups in 2,3-dimethylpyrazine are more easily metalated than either of the CH3 groups in the other isomeric dimethylpyrazines.
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