Ceric acetate

Preparation. Ceric acetate is prepared by ozonolysis of ccrous acetate in the presence of nitrate ion. Stable yellow solid. 

Reaction with olefins, When ceric acetate is healed with styrene in glacial acetic acid containing 10% poiassium acetate at 110° for 20 hr. the major product is the lactone (I), 70% yield, l or the synthetic preparation of lactones, the more available ceric ammonium nitrate can be used in place of ceric acetate. 

In contrast, the photochemical reaction of ceric acetate with fffln.t-/ -methylstyrcnc produces mainly the ester (2) and only minor amounts of lactone (3). 

The reaction of ceric acetate with aromatic hydrocarbons can be used for synthesis of arylacctic acids. Thus the reaction of ceric acetate with toluene in acetic anhydridc-acetic acid gives as the major products benzyl acetate and tolylacetic acid (29% yield). 

ANILINES 4-Chloro-2-pbenylquliiazolme. ANNULENES Propaigyl aldehyde. ANTHRONES Pyiidene hydrochloride. APORPHINES 6-Methoxy-7-hydroxy-3,4-dihydroisoquinoliniuin methiodide. ARYLACETIC ACIDS Ceric acetate. ARYLACETYLENES n-Butylamine. Iodoethynyl(trimethyl)siIane. 

A procedure for the preparation of acenaphthenequinone based upon a postwar disclosure of German work used anhydrous acetic acid as solvent and ceric acetate as catalyst. The dichromate was added to a stirred mixture of the other reagents... 

Catechol, 47, 60, 120, 128, 451, 467-A68, 837, 857, 1011-1012 carbonate, 119-120 dibenzenesulfonate, 47 dichloromethylene ether, 119-120 Catechyl phosphorus trichloride, 120 Cathyl chloride (Ethyl chloroformate), 86, 239, 363, 364-367 Cedrol.913 Cdite, 120 Cellobiose, 893 o-Cellobiose oclaacetate, 158 Cfmulsol, 820 o-Cephalins, 847 Ceric acetate, 1062 Ceric ammonium nitrate, 120-121 Cerous chloride, 121 Cerous hydroxide, 121 Cesium fluoride, 117,121, 933 Cetyl alcohol, 497, 862 Cetyl iodide, 497, 862, 1279 Cetyltrimethylamroonium horohydride, 1143 Cetyltrimelhylaromonium bromide, 121-122 Cevadine, 798 Ovine, 59... 

Other instances included the use of ceric acetate in the synthesis of lactones, although preparation of the reagent was not trivial, and preferable alternatives were subsequently devised (Heiba and Dessau, 1971). Also, a combination of cerium(IV) oxide and hydrogen peroxide was found to oxidize phenols, possibly through the formation of singlet oxygen in situ (Barton et al., 1975). 

Radical Addition.—Ceric acetate reacts with styrene in acetic acid at 110 °C to give the lactones (346) in 60— 70% yield. With lead tetra-acetate (LTA),... 

The triphenylmethoxyacetate was prepared in 53% yield from a nucleoside and the sodium acetate (Ph3C0CH2C02Na, i-Pr3C6H2S02Cl, Pyr) as a derivative that could be easily detected on TLC (i.e., it has a distinct orange-yellow color after it is sprayed with ceric sulfate). It is readily cleaved by NH3/MeOH (100% yield). ... 

The immediate outcome of the Hantzsch synthesis is the dihydropyridine which requires a subsequent oxidation step to generate the pyridine core. Classically, this has been accomplished with nitric acid. Alternative reagents include oxygen, sodium nitrite, ferric nitrate/cupric nitrate, bromine/sodium acetate, chromium trioxide, sulfur, potassium permanganate, chloranil, DDQ, Pd/C and DBU. More recently, ceric ammonium nitrate (CAN) has been found to be an efficient reagent to carry out this transformation. When 100 was treated with 2 equivalents of CAN in aqueous acetone, the reaction to 101 was complete in 10 minutes at room temperature and in excellent yield. 

Graft copolymerization of acrylonitrile with various vinyl comonomers such as methyl acrylate, ethyl acrylate, vinyl acetate, and styrene onto cellulose derivatives using ceric ion was studied [24]. The results showed that... 

Satisfactory 40% peracetic acid is obtainable from Buffalo Electrochemical Corporation, Food Machinery and Chemical Corporation, Buffalo, New York. The specifications given by the manufacturer for its composition are peracetic acid, 40% hydrogen peroxide, 5% acetic acid, 39% sulfuric acid, 1% water, 15%. Its density is 1.15 g./ml. The peracetic acid concentration should be determined by titration. A method for the analysis of peracid solutions is based on the use of ceric sulfate as a titrant for the hydrogen peroxide present, followed by an iodometric determination of the peracid present.3 The checkers found that peracetic acid of a lower concentration (27.5%) may also be used without a decrease in yield. The product was found to be sufficiently pure, after only one recrystallization from 60 ml. of petroleum ether (b.p. 40-60°) and cooling overnight to —18°, to be used in the next step. 

Ammonium hexanitrocerate(IV) [Ceric ammonium nitrate], 55 43 Androst-4-en-3-one, 17(3-(acetoxy)-, [Testosterone acetate], 55, 68, 69 Azide, sodium [Sodium azide] 55, 34... 

Silyi enol ethers can be dimerized to symmetrical 1,4-diketones by treatment with Ag20 in DMSO or certain other polar aprotic solvents." The reaction has been performed with R , R = hydrogen or alkyl, though best yields are obtained when r = r = H. In certain cases, unsymmetrical 1,4-diketones have been prepared by using a mixture of two silyi enol ethers. Other reagents that have been used to achieve either symmetrical or cross-coupled products are iodosobenzene-Bp3-Et20," ceric ammonium nitrate," and lead tetraacetate." If R =0R (in which case the substrate is a ketene silyi acetal), dimerization with TiCU leads to a dialkyl succinate (34, r =0R)." ... 

The diester 110 (E = CC Et) reacts with a mixture of trimethyltin chloride and sodium cyanoborohydride under AIBN catalysis to give the cyclopentane 111 as a 4 1 mixture of cis- and fraws-isomers. The products are destannylated to the acetals 112 by treatment with methanolic ceric ammonium nitrate (CAN). The 1,7-octadienyl derivative 113 was similarly converted into the cyclohexanes 114 (cis/trans = 1 1) (equation 60)67. 

Direct oxidation of oximes is prospective promising procedure for the generation of nitrile oxides. Mercury(II) acetate (54), dimethyldioxirane (55), ceric... 

Materials Required Acetomenaphthone 0.2 g glacial acetic acid 15 ml dilute hydrochloric acid (10% w/v) 15 ml ammonium ceric sulphate 0.05 N ferroin sulphate solution. 

Procedure Weigh accurately about 0.2 g of acetomenaphthone and boil it with 15 ml of glacial acetic acid and 15 ml of dilute hydrochloric acid under a reflux condenser for 15 minutes. Cool the contents carefully and taking adequate precautions to avoid any atmospheric oxidation. Add 0.1 ml of ferroin sulphate solution as indicator and titrate with 0.05 N ammonium ceric sulphate. Repeat the assay without the substance being examined (blank determination) and incorporate the correction, if any. Each ml of 0.05 N ammonium ceric sulphate is equivalent to 0.006457 g of C15H1404. 

Tocopherol acetate 0.3 g Diphenyl amine Each ml of 0.1 N ammonium ceric sulphate = 0.002364 g of C31H5203... 

Exposure of mixtures of alkenes, ceric ammonium nitrate, acetic acid and chloroform to ultrasound leads to a,/i-unsaturated nitroalkenes. A free-radical mechanism was proposed for this reaction (equation 126)410. 

The octadiene 2 appears pure by proton magnetic resonance and elemental analysis. A thin-layer chromatogram [silica, developed with hexane-ethyl acetate (4 1), visualized with 5% ceric ammonium nitrate in 20% sulfuric acid and heating] shows a major spot at Rf =0.4 and a very small impurity at Rf = 0.7. The trace impurity may be removed by crystallization from hexane at —78°. The checkers found that a gas chromatogram (2% Silicone 0V-17... 

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