Resistance organomercury compounds

Robinson, J.B. and O.H. Touvinen. 1984. Mechanisms of microbial resistance and detoxification of mercury and organomercury compounds physiological, biochemical and genetic analysis. Microbiol. Rev. 48 95-124. 

Organomercury compounds found application in organic synthesis from an early date. They are generally stable to attack by atmospheric oxygen although secondary and tertiary alkyls, allyls and benzyls do need some protection. They also resist attack by water and alcohols under neutral conditions and show little or no reactivity towards carbon electrophiles such as carbonyl compounds. 

Organomercury compounds such as phenylmercury acetate, methylmer-cury chloride, methoxjmiercury chloride, react with diphenylcarbazone in the same way as do inorganic mercury compounds, but they are resistant to reduction with zinc dust and are soluble in benzene. They may be detected by paper chromatography on filter paper. ... 

Organomercurials give the reactions shown in Fig. 14.1. Halogenation is useful not only to prepare organic halides but also to determine the position of attachment of the mercury atom in the original compound. Mercury-bound R groups are easily transferred to Pd, and if they resist p elimination, can be used in a variety of transformations shown in Fig. 4.1. 

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