Preparation of trifluoromethyl aryl sulfides using silver(I) trifluoromethanethiolate and an Inorganic Iodide

Adams, D. J. and Clark, J. H. (2000) Preparation of trifluoromethyl aryl sulfides using silver(I) trifluoromethanethiolate and an Inorganic Iodide. Journal of Organic Chemistry, 65(5), pp. 1456-1460. (doi:10.1021/jo9915933) (PMID:10814109)

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Abstract

Reaction of silver(I) trifluoromethanethiolate (AgSCF3) with KI or tetra-n-butylammonium iodide in acetonitrile leads to the formation of a nucleophilic source of trifluoromethanethiolate. This source is capable of converting activated fluoro-, chloro-, bromo-, and iodoaromatics into the corresponding trifluoromethyl aryl sulfides under mild conditions. After successful reaction with tetra-n-butylammonium iodide, crystals of Bu4N[Ag3I4] precipitate from the reaction mixture. With less activated aromatic compounds, decomposition of the trifluoromethanethiolate anion occurs preferentially, giving bis(trifluoromethyl)disulfide, tetrakis(trifluoromethylthio)ethene, and 3,4,5,6-tetrakis(trifluoromethylthio)-1,2-dithiine. The use of copper(I) trifluoromethanethiolate and mercury(II) trifluoromethanethiolate for such reactions has also been investigated.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Adams, Dave
Authors: Adams, D. J., and Clark, J. H.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
ISSN:0022-3263
ISSN (Online):1520-6904
Published Online:15 February 2000

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