Directed ortho-lithiation of lithium thiophenolate. New methodology for the preparation of ortho-substituted thiophenols and related compounds

GD Figuly, CK Loop, JC Martin

文献索引：Figuly,G.D.; Loop,C.K.; Martin,J.C. Journal of the American Chemical Society, 1989 , vol. 111, p. 654

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被引用次数: 113

摘要

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 ...