Journal of Organometallic Chemistry p. 107 - 118 (1982)
Update date:2022-08-16
Topics:
Neugebauer, Wolfgang
Kos, Alexander J.
Schleyer, Rague
Lithiation of biphenyl with 2.4 mol of n-butyllithium in the presence of TMEDA led directly to the 2,2'-dilithio derivative (I) in modest, but preparatively useful yields.I, in turn, was converted to a variety of products.The activation of the 2'-position of 2-lithiobiphenyl was shown directly by a separate experiment.MNDO calculations indicate stabilization in I by double bridging and in 2-lithiobiphenyl by intramolecular ? interaction of Li with the o-phenyl group.Similar interactions in substitution transition states rationalize the specificity of the reactions observed.
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