Ethylene lithiated carbons

We should note that in addition to the above-described surface chemistry, there are reports in the literature on the formation of polymeric species on lithiated carbon electrodes in alkyl carbonate solution. These polymers may include polyethylene (due to polymerization of the ethylene formed by EC reduetion), and polycarbonates (due to polymerization of cyclic alkyl carbonates such as EC) [58,63]. 

Protons attached to sp carbons are more acidic than protons attached to nonallylic sp carbons. Also, the inductive effect of a heteroatom further increases the acidity of an adjacent sp C-H bond, facilitating a-lithiation. The relative activating effect of heteroatoms is sulfur > oxygen > nitrogen. Thus, treatment of 2-ethoxy-l-(phenylthio)ethylene with t-BuLi results in exclusive lithiation at the phenylthio substituted carbon. ... 

Extension to the natural (+) series was accomplished by transfer of chirality from sulfur to carbon via (+ )-2-tolylsulfinyl-2-cyclopentenone, 7 (Scheme 2). The latter was prepared in optically pure form from the ethylene ketal of 2-bromo-2-cyclopentenone 5 by lithiation and treatment with (- )-menthyl p-to-luenesulflnate to yield ( + ) 6, followed by deketalization. Conjugate addition of... 

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