Nitrate ceric ammonium

The dimethyl ethers of hydroquiaones and 1,4-naphthalenediols can be oxidized with silver(II) oxide or ceric ammonium nitrate. Aqueous sodium hypochlorite under phase-transfer conditions has also produced efficient conversion of catechols and hydroquiaones to 1,2- and 1,4-benzoquiaones (116), eg, 4-/-butyl-l,2-ben2oquinone [1129-21-1] ia 92% yield. 

Qualitative. The classic method for the quaUtative determination of silver ia solution is precipitation as silver chloride with dilute nitric acid and chloride ion. The silver chloride can be differentiated from lead or mercurous chlorides, which also may precipitate, by the fact that lead chloride is soluble ia hot water but not ia ammonium hydroxide, whereas mercurous chloride turns black ia ammonium hydroxide. Silver chloride dissolves ia ammonium hydroxide because of the formation of soluble silver—ammonia complexes. A number of selective spot tests (24) iaclude reactions with /)-dimethy1amino-henz1idenerhodanine, ceric ammonium nitrate, or bromopyrogaHol red [16574-43-9]. Silver is detected by x-ray fluorescence and arc-emission spectrometry. Two sensitive arc-emission lines for silver occur at 328.1 and 338.3 nm. 

H2O2—heavy-metal oxide (31), H IO, ceric ammonium nitrate, KNO2, NaBrO, andNaC102. 

The oxidation of 1-nitronaphthalene by ceric ammonium nitrate has been reported (16). The resulting 1-iiitronaphthoquinone condenses with 1,3-butadiene followed by air oxidation under alkaline conditions to form 1-nitroanthraquinone, or l-aminoanthraquinone is formed direcdy by an intramolecular redox reaction. 

Amines can also be protected by this reagent cleavage must be carried c acidic media to avoid amine oxidation. The byproduct naphthoquinone can 1 moved by extraction with basic hydrosulfite. Ceric ammonium nitrate also s as an oxidant for deprotection, but the yields are much lower. 

Dimethoxybenzyl esters prepared from the acid chloride and the benzyl alcohol are readily cleaved oxidatively by DDQ (CH2CI2, H2O, rt, 18 h, 90-95% yield). A 4-methoxybenzyl ester was found not to be cleaved by DDQ. The authors have also explored the oxidative cleavage (ceric ammonium nitrate, CH3CN, H2O, 0°, 4 h, 65-97% yield) of a variety of 4-hydroxy- and 4-amino-substituted phenolic esters. ... 

Ozonolysis, then reduction with Na2S204 at 50°, 57% yield.The 3,4-dimethoxyphenyl derivative was cleaved in 71% yield using these conditions. Ceric ammonium nitrate was reported not to work in this example. 

Ceric ammonium nitrate (CAN), CH3CN, H2O, rt, 12 h, 96% yield. - Benzylamides are not cleaved under these conditions. 

The DAM group, used to protect the —NH group of a /3-lactam, can be cleaved with ceric ammonium nitrate (H2O, CH3CN, 0°, 91 % yield)." ... 

The /7-nitrophenyl ether was used for the protection of the anomeric position of a pyranoside. It is installed using the Konigs-Knorr process and can be cleaved by hydrogenolysis (Pd/C, H2, AC2O), followed by oxidation with ceric ammonium nitrate (81-99% yield). ... 

Ceric ammonium nitrate, MeOH, 0°, 15 min, 82-95% yield. Dioxolanes and some THP ethers are not affected, but in general, with extended reaction times, THP ethers are cleaved. 

Ceric ammonium nitrate converts a 1,4-dimethoxy aromatic compound to the quinone, which is reduced with sodium dithionite to give a depro-tected hydroquinone. ... 

Ceric ammonium nitrate, CH3CN, H2O, 0°, 95% yield. In the presence of chloride ion, cleavage fails." ... 

Ceric ammonium nitrate (CAN), CH3CN, H2O, it, 12 h, 96% yield. Benzylamides are not cleaved under these conditions. Some of the methods used to cleave the benzyl group should also be effective for cleavage of the PMB group. Ceric ammonium nitrate is also used to cleave the PMB group from a sulfonamide nitrogen. ... 

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. 

CAN.ceric ammonium nitrate (ammonium cerium(IV) nitrate)... 

A three-necked round-bottom flask is fitted with a dropping funnel, a thermometer, and a magnetic stirrer and is heated in a water bath to 30°. Tetralin (1.32 g, 0.01 mole) and 50 ml of 3.5 Anitric acid solution are placed in the flask and brought to temperature. Ceric ammonium nitrate (21.9 g, 0.04 mole) is dissolved in 100 ml of 3.5 N nitric acid, and the solution is added dropwise to the reaction mixture at a rate such that the temperature does not rise and only a pale yellow color is evident in the reaction mixture. At the completion of the reaction (1 to 2 hours), the mixture should be colorless. The solution is cooled to room temperature, diluted with an equal volume of water, and extracted twice with ether. The ether solution is dried with anhydrous sodium sulfate, filtered, and the ether is evaporated. The residue may be distilled to yield a-tetralone (bp 113-11676 mm or 170749 mm) or may be converted directly to the oxime, which is recrystallized from methanol, mp 88-89°. 

When ceric ammonium nitrate (CAN) was used as a source of ceric ion, the presence of nitric acid was found to play a significant role. Ceric ion in water is believed to react in the following manner ... 

This technique is based in the fact that when cellulose is oxidized by ceric salts such as ceric ammonium nitrate Ce(NH4)2(N03)6 free radicals capable of initiating vinyl polymerization are formed on the cellulose. However, the possibility remains that the radical formed is an oxygen radical or that the radical is formed on the C-2 or C-3 instead of the C-6 carbon atom. Another mechanism, proposed by Livshits and coworkers [13], involves the oxidation of the glycolic portion of the an-hydroglucose unit. Several workers [14,15], however, have found evidence for the formation of some homopolymer. In the ceric ion method free radicals are first generated and are then capable of initiating the grafting process [16-18]. 

Graft polymerization of methylmethacrylate monomer onto pulps of different residual lignin contents using ceric ammonium nitrate as the initiator was carried out to study the influence of this residual lignin on the graft-ability of these pulps (Fig. 3). From this figure one can... 

Graft copolymerization of methylmethacrylate onto paper wood pulp using ceric ammonium nitrate as the initiator has been studied. Different experimental conditions have been used, including both water and water-organic solvent systems. The effects of composition of the grafting medium and grafting temperature on the grafting process are examined. 

Grafting of methylmethacrylate onto cellulose using ceric ammonium nitrate (Ce ) as the initiator in a benzene-water system is also demonstrated. The grafting yield in a benzene-water system is much lower than in the case of the methanol-water system and decreases by increasing the ratio of benzene to water. This can be due to the lower polarity and wetting power of benzene, which leads to poor swelling of the cellulose. 

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