Lithiated Carbons Containing Heteroatoms

Depending on the precursor and the heat-treatment temperature, the carbonaceous materials discussed so far contain heteroatoms in addition to the prevailing carbon atoms. Even highly crystalline graphite is saturated with heteroatoms at dislocations in the crystallites and at the edges 

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When a heteroatom, such as N, O, or a halogen, is present in a molecule containing an aromatic ring or a double bond, lithiation is usually quite regio-selective. The lithium usually bonds with the sp carbon closest to the hetero atom, probably because the attacking species coordinates with the hetero atom. Such reactions with compounds such as anisole are often called directed metala-tions. In the case of aromatic rings, this means attack at the ortho position.Two examples are... 

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