Information on the reaction path for the 1,2-eliminiation of LiNMe to form benzophenone is provided by the X-ray crystal structure analysis of the tetrahedral adduct [(Ph) (NMe )C(OLi)⋅THF] (a portion of the structure is shown schematically), which is prepared from N,N-dimethylbenzamide and phenyllithium. A N1-Li1 interaction, which is not observed, would lead to loss of the anomeric effect (n →σ ) as well as high conformational strain along the C1-N1 bond.
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