Orthomanganated arenes in synthesis III. Transmetallation of orthomanganated aryl ketones by mercuric chloride; synthesis of ortho-acyl-substituted aryl-mercury(II) compounds

Article abstract of DOI:10.1016/0022-328X(87)85187-2

Mercuric chloride reacts with orthomanganated aryl ketones or esters in refluxing methanol to give the corresponding arylmercury(II) chloride in good yields, with the mercury specifically ortho to the ketone function.Thus the manganated acetophenone gives 2-CH3C(O)C6H4HgCl.Similarly prepared from the corresponding ketones were 2-acetyl-5-methoxyphenylmercury(II) chloride, 2-benzoylphenylmercury(II) chloride and 2-acetyl-3-thienylmercury(II) chloride.The 2-carbomethoxy-4,5,6-trimethoxyphenylmercury(II) chloride was also obtained in good yield from the orthomanganated aryl ester.X-ray crystallographic determination of the structure of 2-CH3C(O)C6H4HgCl shows only a very weak interaction between the mercury atom and the acyl oxygen atom.