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Metallation of the p-xylene compounds p-C6H4(CHRR’)(CHR”R”’) (R,R’,R”,R”’=H or SiMe3) with (tmen=NNN’N’-tetramethylethylenediamine) or (pmdien=NNN’N”N”-pentamethyldiethylenetriamine) occurs selectively at the benzylic carbon atom(s) (Calpha) in a manner dependent on the degree of substitution and the tertiary amine.Four of the organolithium complexes generated have been isolated as crystalline solids and the molecular structure of one, <2>, has been determined from single-crystal X-ray diffraction data.The p-xylenediyl moiety is planar with the trimethylsilyl groups trans to each other, being related by an inversion centre.There is evidence of a dominant p-quinodimethanide bonding contribution, with each lithium, on opposite sides of the C8H6Si2 plane, interacting unsymmetrically with both Calpha and its adjacent ring-carbon atom .A high-yield synthesis of a di-Grignard reagent derived from 1,4-bis(chloromethyl)benzene in thf (tetrahydrofuran) which yields a compound of composition n after ca. 1 h is described.The utility of this compound is illustrated by the synthesis of p-C6H4(CH2SnMe3)2 from SnMe3Cl.
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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI