Iodine-Mercury oxide

Ethanol, Iodine, Mercury oxide See 2-Ethoxy-l-iodo-3-butene... 

During a 1 g mol-scale preparation by a published method from butadiene, ethanol, iodine and mercury oxide, a violent explosion occurred while ethanol was being distilled off at 35°C under slight vacuum. The cause of the explosion could not be established, and several smaller-scale preparations had been uneventful. 

Only the head-to-tail adducts were obtained in the [2+2] photoaddition of 4-hydroxy-l-phenyl[l,8]naphthyridin-2(l//)-one with various alkenes in methanol (Scheme 3). The photolysis of the hypoiodites generated by the in situ reaction of the cycloadducts with excess mercury(ll) oxide-iodine reagent in benzene induced a regioselective scission of the non-ring junction bond of the alkoxyl radical to give substituted 3,9-dihydro-9-phenylyfuro[2,3- ][l,8]naphthyridin-4(2//)-one and/or 3,5-dihydro-5-phenylfuro[3,2-f][l,8]naphthyridin-4-(2//)-ones <1996T6125>. 

Manganese dioxide, 233 Methylmanganese(II) iodide, 211 Organomanganese(II) iodides, 210 Potassium permanganate, 258 Mercury Compounds Iodine-Mercury(II) oxide, 149 Mercury, 174... 

The anomeric hydrogen abstraction can be obtained by an intramolecular Barton type reaction using hydroxyalkylglycosides in presence of iodine and mercury oxide under irradiation. This methodology is used for the synthesis of anomeric spiroorthoesters [6 and 7 in scheme 3). 

O2, ethanol + iodine + mercury oxide (at 35°C), CIO2, crotonaldehyde (above 180°C), buten-3-yne (with heat and pressure). Reaction with sodium nitrite forms a spontaneously flammable product. Exothermic reaction with boron trifluoride etherate + phenol. To fight fire, stop flow of gas. When heated to decomposition it emits acrid smoke and fumes. 

Violent reactions with ammonium salts, chlorate salts, beryllium fluoride, boron diiodophosphide, carbon tetrachloride + methanol, 1,1,1-trichloroethane, 1,2-dibromoethane, halogens or interhalogens (e.g., fluorine, chlorine, bromine, iodine vapor, chlorine trifluoride, iodine heptafluoride), hydrogen iodide, metal oxides + heat (e.g., beryllium oxide, cadmium oxide, copper oxide, mercury oxide, molybdenum oxide, tin oxide, zinc oxide), nitrogen (when ignited), silicon dioxide powder + heat, polytetrafluoroethylene powder + heat. 

The key step in the preparation of the inhibitor is shown in Scheme 1.4.10 and involves the elaboration of the glucose derivative, shown, to the olefin on reaction with methylenetriphenylphosphorane. Once the olefin was isolated, the C-glycoside was obtained via mercury mediated cyclization followed by oxidation of the mercury with iodine. Further elaboration of the resulting iodide gave the desired C-phosphate disaccharide shown. 

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