Mercury organic synthesis

Mercuric chloride is widely used for the preparation of red and yellow mercuric oxide, ammoniated mercury/7(9/USP, mercuric iodide, and as an intermediate in organic synthesis. It has been used as a component of agricultural fungicides. It is used in conjunction with sodium chloride in photography (qv) and in batteries (qv), and has some medicinal uses as an antiseptic. 

Mercuric Nitrate. Mercuric nitrate [10045-94-0] Hg(N02)2, is a colorless dehquescent crystalline compound prepared by the exothermic dissolution of mercury in hot, concentrated nitric acid. The reaction is complete when a cloud of mercurous chloride is not formed when the solution is treated with sodium chloride solution. The product crystallizes upon cooling. Mercuric nitrate is used in organic synthesis as the starting material and for the formulation of a great many other mercuric products. 

Uses Determining refractive index of minerals paint diluent dyed hexane is used in thermometers instead of mercury polymerization reaction medium calibrations solvent for vegetable oils alcohol denaturant chief constituent of petroleum ether, rubber solvent, and gasoline in organic synthesis. 

Uses Determining fat content in milk solvent for alkaloids, fats, oils manufacturing isovaleric acid, isoamyl or amyl compounds, esters, mercury fulminate, artificial silk, smokeless powders, lacquers, pyroxylin photographic chemicals pharmaceutical products microscopy in organic synthesis. 

Mercury(II) nitrate is used in the preparation of other mercury compounds in organic synthesis and as an analytical standard for mercury. 

This reaction is widely utilised in organic synthesis, when carbonyl groups may be protected as the thioacetals or thioketals. Unlike acetals or ketals, the thio compounds do not undergo acid catalysed hydration, and may be used in acidic reaction conditions. The metal-directed hydrolysis is rationalised in terms of the soft-soft interaction of the sulfur with the metal cation, in contrast to the hard-soft interaction with a proton. Hydrolysis is readily achieved on treatment with aqueous mercury(n) or silver(i) salts. Once again, the... 

Recently, in consideration of the environment, heavy metal oxidants such as lead(IV),thallium(III), and mercury(II) cannot be used for industrial processes, especially for pharmaceutical and agrochemical processes, due to their high toxicity and serious amount of metal waste. Hypervalent iodine reagents are now extensively used in organic synthesis as a mild, safe, and economical alternative for heavy metal reagents (Fig. 1). 

A. J. Bloodworth, The Organic Chemistry of Mercury, C. A. McAuliffe, Ed., Macmillan, London, 1977. R. C. Larock, Organomercury Compounds in Organic Synthesis, Springer-Verlag, Berlin, 1985. 

S-Orthoesters seldom appear in organic synthesis but they do occupy one useful niche. In 1967 Seebach245-246 introduced tris(methylthio)methyhithium as an acyl anion equivalent of a carboxyl group. It was sufficiently stable and nucleophilic to react with a range of electrophiles. For example, nucleophilic substitution of the allylic chloride 121,1, followed by mercury(Il)-mediated hydrolysis of the SS-orthoester intermediate 121,2, gives the p,y-unsaturated car-... 

Mercury(II) trifluoroacetate finds frequent employment in organic synthesis 223, 229, 230) since it adds rapidly, stereospecifically, and quantitatively across nonconjugated olefinic bonds, for example, Eq. (21). The mercurated products thus prepared may be readily converted... 

The last major development is not of a purely analytical nature it is based on the idea of applying polarographic results for working out electrochemical routes of organic synthesis. The experience obtained from d.c. polarographic experiments can be utilized. By preparative electrolysis in extremely small volumes (about 1 ml) with a dropping mercury electrode in connection with the identification of products thus... 

Tor a review of the use of phenyl(trihalomethyl)mercury compounds as dihalocarbene or dihalocarbenoid precursors, see Seyferth, D. Acc. Chem. Res. 1972, 5, 65. For a review of the synthesis of cyclopropanes with the use of organomercury reagents, see Larock, R.C. Organomercurcury Compounds in Organic Synthesis, Springer, NY, 1985, pp. 341-380. 

A procedure for the cathodic reduction of anthranilic acid to the corresponding alcohol is described in Organic Synthesis [36]. Because the carboxylic acid group is so difficult to reduce, the method cannot normally be used for acid substituted with easily reducible functions or groups. For instance, pentafluorobenzoic acid loses fluorine by cathodic cleavage at mercury, in 20% sulfuric acid, at —1.20 V (SCE) 2,3,5,6-tetrafluor-obenzoic acid is obtained in 75% yield [38]. However, at potentials more negative than... 

Addition of electrophilic mercury(n) salts to carbon-carbon double bonds in nucleophilic solvents (i.e. oxyrncrcuration, solvomercuration etc.) is a well documented methodology in organic synthesis " . In these reactions a mercuric salt, usually the chloride or... 

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