Organomercury compounds. XXVI. Thermal decomposition of mercuric 2,6-disubstituted benzoates

G. B. Deacon, G. N. Stretton

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Abstract

The main thermal decomposition path for mercuric 2,6-disubstituted benzoates, (RCO2)2Hg (R = 2,6-X2C6H3; X = F, Cl, Br, or Me), can be varied considerably. In boiling dimethyl sulphoxide, decarboxylation occurs giving the corresponding diarylmercurial (X = F or Cl) or RHgO2CR derivative (X = Me or Br). There is considerable competition from reaction of the mercuric salt with the solvent in the last three cases. With boiling pyridine as medium, the 2,6-difluorobenzoate yields a mixture of R2Hg and RHgO2CR derivatives, but the 2,6-dichlorobenzoate only gives (RCO2)2Hg(py)2. Thermal decomposition of the mercuric benzoates under vacuum yields the carboxylic acids and complex mercuration products, mainly based on 3-mercurated 2,6-disubstituted benzoates, with partial additional mercuration and/or decarboxylation. Pyrolysis of mercuric 2,6-dichlorobenzoate at atmospheric pressure results in both mercuration and decarboxylation, giving m-dichlorobenzene as the main volatile product and a complex mercurial with 1,3-dimercurated-2,6-dichlorobenzene repeating units and 2,6-dichlorophenyl terminal groups. 

Original languageEnglish
Pages (from-to)123-136
Number of pages14
JournalJournal of Organometallic Chemistry
Volume218
Issue number1
DOIs
Publication statusPublished - 22 Sep 1981

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