Phenyl mercury compounds

Phenyl mercury compounds are more efficiently absorbed in the gastrointestinal tract of the rat than inorganic mercuric mercury, but less effectively than methyl mercury compounds (Ellis and Fang, 1967). Figures concerning man are not available. Absorbed phenyl mercury is distributed in blood similarly to methyl mercury, i.e. about 90% is present in the erythrocytes (Berlin, 1963 b). Initially, a large pro-... 

Diphenylmercury is easily made by reduction of almost any phenyl-mercury compound PhHgX (some of which are commercially available and fairly cheap) by hydrazine hydrate and sodium carbonate in aqueous ethanol. 

It is theoretically possible for the reducing column to reduce disulfide bridges in papain, thus enabling 6 moles of mercurial to combine with each mole of protein. This possibility seems remote since dialyzed crystalline papain in ethanolic solution combines in the same molar ratio. Moreover, such a reduction of S—S bonds does not occur with serum albumin (48). Previous experience with PCMB (74) has provided no evidence that this compound can split disulfide bonds. It should be noted that papain after combination with 6 moles of PCMB is inactive treatment with cysteine and Versene regenerates only a portion of the original proteolytic activity. It appears likely that some modification of the native structure of papain occurs in ethanolic solution in the presence of the phenyl mercury compounds which permits combination in the 6 to 1 ratio. 

More useful for synthetic purposes, however, is the combination of the zinc-copper couple with methylene iodide to generate carbene-zinc iodide complex, which undergoes addition to double bonds exclusively to form cyclopropanes (7). The base-catalyzed generation of halocarbenes from haloforms (2) also provides a general route to 1,1-dihalocyclopropanes via carbene addition, as does the nonbasic generation of dihalocarbenes from phenyl(trihalomethyl)mercury compounds. Details of these reactions are given below. 

III. Dihalocarbenes from Phenyl(trihalomethyl)mercury Compounds... 

Seyferth (7) discovered that phenyl(trihalomethyl)mercury compounds decompose when heated in a solvent giving dihalocarbenes. When the solvent contains a suitable olefin, carbene addition occurs giving 1,1-dihalocyclopropane derivatives. The reaction has the advantage that strong base is not required in the reaction mixture, and base-... 

Kimura and Miller [28] collected and determined vapours produced by the decomposition in soil of phenyl alkylmercury compounds. They found that the air above soil containing phenylmercury acetate contained mercury vapour and traces of phenylmercury acetate. 

Organic mercury compounds, especially phenyl and methoxyethyl mercury may also be biotransformed into inorganic mercury by cleavage of the carbon-mercury bond. Although such compounds are more readily absorbed than inorganic mercury compounds, the toxicity is similar. 

The crystal structures of methyl- and phenyl-mercury(II) dithizonates have been determined as part of a study on the photochroism of such compounds.149 In both structures the chelate is planar, with an irregular three-coordination at the metal including N and S of the ligand. The article provides a short structural review of dithizone complexes. 

The observation that phenyl(trichloromethyl)mercury undergoes dissociation at 150 °C to give phenyl-mercury(II) chloride and dichlorocarbene has led to a wide range of organomercury compounds (PhHgCX3 — Seyferth reagents)15-18 which serve as efficient dihalocarbene transfer reagents (equation... 

The thermal decomposition of phenyl(trihalomethyl)-mercury compounds, C6H5.Hg.CX3, in the presence of olefins yields the dihalo-cyclopropane virtually quantitatively. A typical example is expressed in equation (15). The initial rate of disappearance of the organometallic... 

A number of phenols, especially chlorinated phenols and certain metal-organic compounds, such as copper naphthenate and phenyl mercury oleate, are effective preservatives. Pentachlorophenol and copper naphthenate are most commonly used, and are carried into the wood in 1-5 percent solutions in petroleum oil. Pentachlorophenol is colorless, and can be applied in clear volatile mineral oils to mill-work and window sash requiring a clean, nonswelling, and paintable treatment. 

It is most conveniently stored in glass ampuls. Several other preparations for this compound are known including reactions of dihydroxy(phenyl)borane and boron trichloride12 13 or phosphorus pentachloride,14 2,4,6-triphenylboroxin, [C6H5BO]3, with phosphorus pentachloride,14 phenyl mercury chloride with boron trichloride,15 and benzene with boron trichloride.16... 

Mercury diphenyl has been prepared in a number of ways. The most important methods are by the action of sodium on a mixture of bromobcnzene and mercuric chloride 1 from sodium amalgam and phenyl mercuric iodide 2 by the interaction of phenyl mercuric bromide and potassium sulfide2 or phenyl mercuric acetate and sodium stannite 3 from phenyl magnesium bromide and mercuric chloride 4 by the action of phenyl hydrazine on mercury compounds 5 from mercuric chloride and phenyl arsenious oxide 6 and from diphenyl mercuric ammonium acetate and sulfur compounds.7... 

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