Abstract
The directed ortho-lithiation of lithium thiophenolate by reaction with n-butyllithium in cyclohexane with N,N,- N',N'-tetramethylethylenediamine gives almost quantitative conversion to lithium 2-lithiobenzenethiolate (1). Reactions of this dilithio derivative with a variety of electrophiles (DzO, carbon dioxide, acetone, diphenyl disulfide, methyl iodide, and thioxanthone) are described. The adduct to thioxanthone is ring-closed to form a triarylmethyl cation (9), and its related carbinol (8), with two o,o'-sulfide bridges.
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