Chloro mercuration

In a similar way, aniline, the three toluidines, and the aminophenols can be converted into the corresponding chloro-mercuric compounds in about 40 per cent yields. 

Acetamido-4-methylselenazole can react with mercuric acetate to yield 5-mercuriacetate derivatives that can be converted to the chloro derivatives by the action of sodium chloride. Treatment with potassium iodide leads to reduction regenerating the initial compound with loss of mercury (Scheme 16) (4). 

The earliest oxidations were effected with nitrous fumes and later with mercuric oxide and isoamyl nitrite.74 Lead tetraacetate in acetic acid is in many cases the reagent of choice, but the removal of by-products can present some difficulties.75 IV-Haloimides and amides in alcoholic solutions have been reported to yield essentially pure tetrazolium salts76 and have been found specially useful in the preparation of heteroaryl-substituted tetrazolium salt.77,78 The novel formazans 49 have been successfully oxidized to 50 using 7V-chloro succinimide (Eq. II).79 tert-Butyl hypo-... 

In an attempt to employ this route Curd, Rose et al. 58) treated p-chloro-phenylamidinothiourea with isopropylamine and mercuric oxide, but obtained mostly N-p-chlorophenyl-N -cyanoguanidine. Efforts to improve the results by numerous changes in conditions were unsuccessful in all cases biguanides were merely by-products, formed in yields less than 5%. A later patent 154) has however claimed the successful use of this route. 

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. 

Mercury(II) acetate in acetic acid reacts with allyl chloride and methanol to produce 3-chloro-2-methoxypropyl mercuric acetate, C1CH2CH(0CH3)-CH2Hg0C(=0)CH3. The compound is difficult to isolate from the solution and generally an ammoniacal solution is used for commercial applications. 

On heating with hydrochloric acid the salt changes to chloro-pent-ammino-ehromie chloride, [Cr(NH3)5Cl]Cl2. A concentrated solution gives with mercuric chloride a yellowish-red, sparingly soluble double salt, [Cr(NH3)5H20]Cl3.(HgCl2)3.H20. 

Synonym Gamma-Chloropropylene Oxide 3-Chloro-1,2-Propylene Oxide Chlorosulfonic Acid Chlorothene Chiorotoluene, Alpha Alpha-Chlorotoluene Omega-Chlorotoluene Chlorotrifluoroethylene Chlorotrimethylsilane Chlorsulfonic Acid Clilorylen Clip Chromic Acid Chromic Anhydride Chromic Oxide Chromium (VI) Dioxychloride Chromium Oxychloride Chromium Trioxide Chromyl Chloride Cianurina Citric Acid Citric Acid, Diammonium Salt Clarified Oil Clorox Cc Ral Coal Tar Oil Cobalt Acetate Cobalt Acetate Tetrahydrate Cobalt (II) Acetate Cobalt Chloride Cobalt (II) Chloride Cobaltous Acetate Cobaltous Chloride Cobaltous Chloride Dihydrate Cobaltous Chloride Hexahydrate Cobaltous Nitrate Cobaltous Nitrate Hexahydrate Cobaltous Sulfate Heptahydrate Cobalt Nitrate Cobalt (II) Nitrate Cobalt Sulfate Compound Name Epichlorohydrin Epichlorohydrin Chlorosulfonic Acid Trichloroethane Benzyl Chloride Benzyl Chloride Benzyl Chloride Trifluorochloroethylene Trimethylchlorosilane Chlorosulfonic Acid Trichloroethylene Cumene Hydroperoxide Chromic Anhydride Chromic Anhydride Chromic Anhydride Chromyl Chloride Chromyl Chloride Chromic Anhydride Chromyl Chloride Mercuric Cyanide Citric Acid Ammonium Citrate Oil Clarified Sodium Hypochlorite Coumaphos Oil Coal Tar Cobalt Acetate Cobalt Acetate Cobalt Acetate Cobalt Chloride Cobalt Chloride Cobalt Acetate Cobalt Chloride Cobalt Chloride Cobalt Chloride Cobalt Nitrate Cobalt Nitrate Cobalt Sulfate Cobalt Nitrate Cobalt Nitrate Cobalt Sulfate... 

Ferrocene, like thiophene, furan, and other so-called superaromatic systems, reacts readily with mercuric acetate to form mercurated derivatives. Nes-meyanov and coworkers first reported that ferrocene could be mercurated under relatively mild conditions in either ethyl ether-alcohol or benzene-alcohol solution (63). The acetoxymercuriferrocenes formed in this manner are usually treated with an alcoholic solution of an alkali metal halide. The resulting products, chloro-mercuriferrocene (XXVII) and l,l -di(chloromercuri)ferrocene (XXVIII), can be conveniently separated by extraction with n-butyl alcohol. 

Organic compounds Organic fluorine compounds arc made by reaction of the corresponding alkane chloro-compounds with silver fluoride, mercurous fluoride, antimony trifluoride, titanium tetrafluoridc. and the arene fluoro-compounds by the diazo-reaction using hydrogen fluoride, and otherwise. The effect of the continued replacemenl of hydrogen atoms by fluorine atoms is an initial increase in reactivity, followed by a reversal of this effect, so lhal the highly substituted compounds arc relatively inert, See also Fluorocarbon. 

Amino-8-bromophenanthridone can be deaminated smoothly by the action of cold hypophosphorus acid on the diazonium chloride.122 1-Bromophenanthridone is formed in moderate overall yield from the amino compound when the diazonium bromide-mercuric bromide complex is heated at 120° and a number of bromo- and chloro-phen-anthridones have been obtained recently by Sandmeyer procedures.26, 101... 

For the preparation of chlorides or bromides, the diazonium salt is decomposed with a solution of cuprous chloride or bromide in the corresponding halogen acid (Sandmeyer reaction). It is possible to prepare the aryl bromide from the diazonium chloride or sulfate. A variation Involves the use of copper powder and a mineral acid for the decomposition step (Gattermann reaction). Both procedures are illustrated by the syntheses of the isomeric bromotoluenes and chlorotoluenes. The usual conditions of the Sandmeyer reaction fail in the preparation of the chloro- and bromo-phenanthrenes. However, these compounds can be successfully obtained by the interaction of the diazonium compound with mercuric and potassium halides (Schwechten procedure). Another procedure for formation of aryl bromides involves treatment of the amine hydrobromide with nitrogen trioxide in the presence of excess 40% hydro-bromic acid. The Intermediate diazonium perbromide is then decomposed by heat. ... 

The addition of a chloromethyl ether to olefinic linkages takes place under conditions similar to the Friedel-Crafts reaction and leads to y-chloro ethers. Substitution of zinc chloride for mercuric chloride as catalyst has improved the yields. Allyl chloride and chloromethyl ether react to give a high yield of l-methoxy-3,4-dichlorobutane (98%). ... 

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