Lithiation of N,N,N',N'-Tetramethylethylenediamine and the Structure in a Mixed Organolithium Aggregate.
The dilithiation of 2-methyl-6-tert-butylphenol with 2 equiv BuLi/tmeda (tmeda = N,N,N',N'-tetramethylethylenediamine) in refluxing hexane results in low yields of the dilithiated product due to formation of lithiated tmeda as a side product. Excess BuLi/tmeda yields good conversion and crystals of a mixed aggregate consistent with the dilithiated product, lithiated tmeda, and tmeda. The structure of the mixed aggregate, revealed by single crystal x-ray diffraction, shows the 1st structural data for a lithiated tmeda mol.
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