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Directed lithiation of arenethiols

Smith, Keith, Lindsay, Charles M. and Pritchard, Gareth J. 1989. Directed lithiation of arenethiols. Journal of the American Chemical Society 111 (2) , pp. 665-669. 10.1021/ja00184a040

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Benzenethiol, toluene-4-thio1, and 3,5-dimethylbenzenethiol are doubly lithiated (on sulfur and on carbon) by n-butyllithium in tetramethylethylenediamine. C-Lithiation occurs ortho to the thiol group, and subsequent treatment with electrophiles provides a convenient approach to ortho-substituted arenethiol derivatives. The reactions with tetraisopropylthiuram disulfide provide direct access to the corresponding o-phenylene trithiocarbonates. Double lithiation of 4-methoxybenzenethiol results in C-lithiation adjacent to the methoxy group rather than the thiolate residue, indicating that methoxy is a more powerfully ortho-directing substituent in this type of metalation reaction. 3-Methoxybenzenethiol is lithiated between the methoxy and thiolate groups.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: American Chemical Society
ISSN: 0002-7863
Last Modified: 04 Jun 2017 02:50

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