Organomercury Compounds. XXIV Facile syntheses of polyfluoroarylmercurials by mercuration reactions

G. B. Deacon, D. Tunaley

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Abstract

The polyfluoroarylmercuric chlorides, RHgCl (R = C6F5, p-MeOC6F4, p-MeC6F4, m-HC6F4, o-HC6F4, p-HC6F4, m-O2NC6F4, o-O2NC6F4, p-BrC6F4, m-BrC6F4, o-BrC6F4, p-HOC6F4, p-H2NC6F4, m-HO2CC6F4, p-(p-HC6F4)C6F4, 3,5-H2C6F3, 3-bromo-2,4,6-trifluorophenyl or 3-bromo-2,5,6-trifluorophenyl), and the bis (polyfluorophenyl)mercurials, R2Hg (R = C6F5, p-MeOC6F4, p-MeC6F4, p-HC6F4, m-O2NC6F4,o-O2NC6F4, p-BrC6F4, m-BrC6F4, o-BrC6F4, p-HOC6F4, orp-H2NC6F4) have been prepared by mercuration of the appropriate polyfluoroarenes with mercuric trifluoroacetate and trifluoromethanesulphonic acid in trifluoroacetic acid, followed by treatment of the products with hydrochloric acid (RHgCl derivatives) or potassium bromide (R2Hg derivatives). For R = p-MeOC6F4, the actual mercuration product has been isolated and identified as 2,3,5,6-tetrafluoro-4-methoxyphenylmercuric trifluoromethane sulphonate. Interaction of mercuric trifluoroacetate with trifluoromethanesulphonic acid in trifluoroacetic acid yields mercuric trifluoromethanesulphonate, which is considered to be the mercurating agent, and which has been characterized as the complex, [Hg(bpy)3](O3SCF3)2·H20 (bpy = 2,2′-bipyridyl). The mercuration syntheses are very simple and convenient, and should become the preferred method for most polyfluoroarylmercurials.

Original languageEnglish
Pages (from-to)403-426
Number of pages24
JournalJournal of Organometallic Chemistry
Volume156
Issue number2
DOIs
Publication statusPublished - 22 Aug 1978

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