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Concept
Organomercury chemistry
Summary
Organomercury chemistry refers to the study of organometallic compounds that contain mercury. Typically the Hg–C bond is stable toward air and moisture but sensitive to light. Important organomercury compounds are the methylmercury(II) cation, CH3Hg+; ethylmercury(II) cation, C2H5Hg+; dimethylmercury, (CH3)2Hg, diethylmercury and merbromin ("Mercurochrome"). Thiomersal is used as a preservative for vaccines and intravenous drugs.
The toxicity of organomercury compounds presents both dangers and benefits. Dimethylmercury in particular is notoriously toxic, but found use as an antifungal agent and insecticide. Merbromin and phenylmercuric borate are used as topical antiseptics, while nitromersol is used as a preservative for vaccines and antitoxins.
Organomercury compounds are generated by many methods, including the direct reaction of hydrocarbons and mercury(II) salts. In this regard, organomercury chemistry more closely resembles organopalladium chemistry and contrasts with organocadmium compounds.
Electron-rich arenes undergo mercuration upon treatment with Hg(O2CCH3)2. The one acetate group that remains on mercury can be displaced by chloride:
C6H5OH + Hg(O2CCH3)2 → C6H4(OH)–2-HgO2CCH3 + CH3CO2H
C6H4(OH)–2–HgO2CCH3 + NaCl → C6H4(OH)–2-HgCl + NaO2CCH3
The first such reaction, including a mercuration of benzene itself, was reported by Otto Dimroth between 1898 and 1902.
The Hg2+ center binds to alkenes, inducing the addition of hydroxide and alkoxide. For example, treatment of methyl acrylate with mercuric acetate in methanol gives an α--mercuri ester:
Hg(O2CCH3)2 + CH2=CHCO2CH3 → CH3OCH2CH(HgO2CCH3)CO2CH3
The resulting Hg-C bond can be cleaved with bromine to give the corresponding alkyl bromide:
CH3OCH2CH(HgO2CCH3)CO2CH3 + Br2 → CH3OCH2CHBrCO2CH3 + BrHgO2CCH3
This reaction is called the Hofmann-Sand Reaction.
A general synthetic route to organomercury compounds entails alkylation with Grignard reagents and organolithium compounds.
Official source
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