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 |
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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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