Thiophenol anion reaction with halides

Aryl radicals electrochemically generated from the cleavage of aryl halide radical anions have been observed to react with nucleophiles other than iodide (Pinson and Saveant, 1974, 1978 Saveant, 1980), a reaction known as the SrjjI reaction (Bunnett, 1978). The most commonly used nucleophiles are thiophenolate, mercaptides, and cyanide ion. The reactions observed are... 

The phenyl sulfides available permit the synthesis of organolithium by reaction (c) (see Table 2), e.g., tertiary alkyllithiums that are not available from the corresponding halides and sulfur-stabilized vinyllithiums that serve synthetically as acyl anion equivalents. Also, the benzyl ether moiety is not cleaved when the substrate contains both this moiety and a thiophenol group, and bis(phenyl sulfides) may be treated with 1-2 equiv of Li metal to give the mono- or dilithiums, respectively. 

---