1-oxide mercuration

Mercuric Oxide. Mercuric oxide[21908-53-2] HgO, is a red or yellow water-insoluble powder, rhombic in shape when viewed microscopically. The color and shade depend on particle size. The finer particles (< 5 -lm) appear yellow the coarser particles (> 8 -lm) appear redder. The product is soluble in most acids, organic and inorganic, but the yellow form, which has greater surface area, is more reactive and dissolves more readily. Mercuric oxide decomposes at 332°C and has a high (11.1) specific gravity. 

Galen, a physician whose views outUved him by about a thousand years, died about 200 AD. He beUeved that mercurials were toxic, and did not use any mercury compound therapeutically. However, as a result of Arabian influence, the therapeutic uses of mercury were slowly recognized by Western Europe. In the thirteenth century mercury ointments were prescribed for treating chronic diseases of the skin. Mercury and its compounds, such as mercurous chloride, mercuric oxide, mercuric chloride, and mercuric sulfide, were used widely from the fifteenth to the nineteenth centuries, and to some extent in the twentieth century. During the first half of the twentieth century, the primary therapeutic uses of mercury included bactericidal preparations, such as mercuric chloride, mercuric oxycyanide, and mercuric oxide and diuretics, such as aryl HgX (Novasural) and mercurated ahyl derivatives (14). 

The more generally known mercuric oxide-mercuric chloride hydrolysis 2 may also be used, and in the present case it gives a yield of about 90%. The reductive desulfurization of Part E is also based on the work of Mukaiyama.12 It is clearly superior to Raney nickel desulfurization, which gives only 36-45% of 3-benzylindole. 

Mercury Mercuric iodide Mercuric nitrate Mercuric oxide Mercurous nitrate Mercuric sulphate Mercuric sulphide Mercurous sulphate... 

Zinc enolate 4, prepared from acetylene ether pyridine i-oxide, mercuric chloride, and zinc, adds to aldehydes to form a-chloro-3-hydroxy esters 5 in good yields ( ). Subsequent treatment with base gives trans-epoxyesters, one of which 6 is converted to 2-amino-2-deoxy-D-ribose stereoselectively in good yields (O. 

Mercuration of quinoline N-oxide in acetic acid or perchloric acid gives the 8-mercurio-chloride (26) as the main product and small amounts of the 3-, 5-, 6- and 7-isomers. In the absence of solvent mercury(II) sulfate gives all the possible isomers although the total yield is poor. 6-Methylquinoline N-oxide gives the 8-substituted derivative (27). The preferential 8-orientation is accounted for in terms of preliminary coordination of the mercury atom at the oxygen of the N-oxide. When the 8-position is blocked, as in 8-bromoquinoline N-oxide, mercuration is reported to occur at the 4-position (55YZ490, 69CPB906). 

One of the most versatile methods for the preparation of 1,1-disubstituted X -phosphorins 124 was discovered by Stade who found that X -phosphorins 2 can be oxidized (mercuric acetate gives the best results) in the presence of alcohols or phenols in benzene to 1.1-dialkoxy- or l.l-diphenoxy-X -phosphorins 124. The first step is probably a reaction of the soft X -phosphorin- jr-system with the soft acid Hg which by electron transfer leads to the weakly electrophilic radical cation 58. This is then attacked by alcohol or phenol - or as Hettche has found by other nucleophiles such as an amine to form by loss of a proton the neutral X -phosphorin radical 59. This radical is oxidized once again by mercury ions leading to the formation of elemental mercury and the strongly electrophilic, short-lived X -phosphorin cation 127, which is immediately attacked by alcohol, phenol or amine. Loss of a proton then leads to the X -phosphorin 124. It is also conceivable that 59 can couple directly with a radical to form 124 (Method E, p. 82). 

Compound Name Mercuric Chloride Mercuric Iodide Mercuric Chloride Mercuric Ammonium Chloride Mercuric Cyanide Mercuric Cyanide Mercuric Chloride Mercuric Nitrate Mercuric Oxide Mercuric Chloride Mercuric Nitrate Mercurous Chloride Mercurous Nitrate Mercurous Chloride Mesityl Oxide Calcium Resinate Methyl Methacrylate N-Butyl Methacrylate Glycidyl Methacrylate Ethyl Methacrylate Methyl Methacrylate Methallyl Chloride Methallyl Chloride Formaldehyde Solution Methane... 

Hydroxide precipitation with sodium or calcium hydroxide is the standard method used for treating heavy metal wastes. Sodium hydroxide was used in this study because it forms an insoluble oxide, mercuric oxide, when added to the spent plating bath. The pH should be increased to between 10 and 12. The filtrate still contained a high level of mercuric chloride in solution and had to be treated before disposal. 

With excess of mercuric oxide, mercuric sulphate is also formed.1 Selenium is attacked rapidly by sulphuryl chloride ... 

Yokoyama, M., Ishihara, H., Iwamoto, R., and Tadokoro, H. (1969) Structure of Poly(ethylene oxide) Complexes. III. Poly(ethylene oxide)-Mercuric Chloride Complex. Type II, Macromolecules 2, 184-192. 

Photochemical Oxidation.—Mercuric chloride solution is reduced by ferrous chloride under the influence of light, mercurous chloride being precipitated. 

Ignition on contact with furfuryl alcohol powdered metals (e.g., magnesium iron) wood. Violent reaction with aluminum isopropoxide -f- heavy metal salts charcoal coal dimethylphenylphosphine hydrogen selenide lithium tetrahydroaluminate metals (e.g., potassium, sodium, lithium) metal oxides (e.g., cobalt oxide, iron oxide, lead oxide, lead hydroxide, manganese oxide, mercur oxide, nickel oxide) metal salts (e.g., calcium permanganate) methanol + phosphoric acid 4-methyl-2,4,6-triazatricyclo [5.2.2.0 ] undeca-8-ene-3,5-dione + potassium hydroxide a-phenylselenoketones phosphorus phosphorus (V) oxide tin(II) chloride unsaturated organic compounds. 

Acid acceptors Lead acetate trihydrate. 2,6-Lutidine. Magnesium oxide. Mercuric oxide. Pyridine. Sodium acetate. 

Pseudovmcadifformine (680), prepared from catharanthine by reduction (sodium borohydride, then hydrogen-platinum oxide) followed by oxidation (mercuric acetate), undergoes the same rearrangement as vincadifformine (76) when oxidized, then treated with triphenylphosphine and acetic acid. The products are pseudovincamine (681) and its C-16 epimer 682 (Scheme 96), and it is of interest that these compounds were prepared by this transformation well before this ring system was found in Nature (5S5). 

ACETYL NITRATE (591-09-3) C2H3NO4 self-reactive thermally unstable above 131 to 212°F/55 to 100°C, depending on solution strength, Violent reaction with strong oxidizers, mercuric oxide. 

IODINE (7553-56-2) A powerful oxidizer. Material or vapors react violently with reducing agents, combustible materials, alkali metals, acetylene, acetaldehyde, antimony, boron, bromine pentafluoride, bromine trifluoride, calcium hydride, cesium, cesium oxide, chlorine trifluoride, copper hydride, dipropylmercury, fluoride, francium, lithium, metal acetylides, metal carbides, nickel monoxide, nitryl fluoride, perchloryl perchlorate, polyacetylene, powdered metals, rubidium, phosphorus, sodium, sodium phosphinate, sulfur, sulfur trioxide, tetraamine, trioxygen difluoride. Forms heat- or shock-sensitive compounds with ammonia, silver azide, potassium, sodium, oxygen difluoride. Incompatible with aluminum-titanium alloy, barium acetylide, ethanol, formamide, halogens, mercmic oxide, mercurous chloride, oxygen, pyridine, pyrogallic acid, salicylic acid sodium hydride, sodium salicylate, sulfides, and other materials. 

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