Anthracene dissolving metals

By and large, a hnely divided precipitate of a metal is a very effective one-electron reducer. For example, a hnely divided precipitate of Zr(0) was obtained on mixing naphthalene sodium derivative in THF with ZrCl4. The Zr(0) precipitate dissolved on addition of anthracene or benzophenone to form the corresponding zirconium salts of the anion-radicals (Terekhova et al. 1996). 

Imino-10-oxospiro[anthracene-9,r-cyclohexane]-3-carbonitrile (45). Compound 44 (1.5 g, 5 mmol) was dissolved in 25 ml of toluene. To this, pulverized sodium (0.12 g, 5 mmol) was then added. The reaction mixture was refluxed for 8 h. To this reaction mixture, a little methanol was added to react with the unreacted sodium metal. From the reaction mixture, solvent was removed by vacuum distillation and the remaining solid contents were poured onto crushed ice and acidified using aqueous 2 N HCl to pH 2-3. The dark colored solid obtained was then filtered, washed with water, vacuum dried, and recrystallized from benzene/pet ether to afford pure compound 45 (1.11 g, 74%). 

Effluents from the manufacture of Pb(CH3)4 can be treated with an alkali metal borohydride, e.g., NaBH4 at pH 8 to 11 to substantially reduce the level of dissolved lead compounds, like [Pb(CH3)3][145, 146]. Zn can also be used [147]. Liquid NH3 and toluene are used to remove solid NH4Clfrom the apparatus for producing Pb(CH3)4 by the NH3- or amine-catalyzed reaction of CH3CI with a PbNa alloy [148]. Stabilization of Pb(CH3)4, and of antiknock fluids containing Pb(CH3)4, is accomplished by addition of compounds, like toluene [149], xylene [141, 150], styrenes [151], naphthalenes [149, 151, 152], anthracenes [152], substituted phenols [141, 152 to 155], olefinic hydrocarbons [152], alcohols [141, 152], amines [155], hydroquinones [156], ethers [141], saturated or unsaturated carboxylic acids [141, 152], esters of phosphoric acid [152], or of sulfuric acid [157], or of sulfonic acids [141], imidazoles [158], alkyl halides and alkyl thiocyanates [141], or tall oil [159] see also Organolead Compounds , Vol. 2, Section 1.1.1.2, to be published. 

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