Ceric Ammonium Nitrate Catalyzed Oxidation of Aldehydes and Alcohols

A variety of aromatic, aliphatic and conjugated aldehydes and alcohols were transformed to the corresponding carboxylic acids and ketones with a quantitative conversion in high yields with 70% t‐BuOOH solution in water in the presence of catalytic amounts of ceric ammonium nitrate [Ce(NH₄)₂(NO₃)₆] (CAN) under room temperature conditions. The scope of our catalytic system is applicable for a wide range of aromatic, conjugated and aliphatic substrates. These aldehydes were converted to the corresponding carboxylic acids in good isolated yields in reasonable times. This method possesses a wide range of capabilities since it can be used with other functional groups which may not tolerate oxidative conditions, involves fairly simple method for work‐up, exhibits chemoselectivity and proceeds under ambient conditions. The resulting products are obtained in good yields within reasonable time.     

Mild,Efficient and Selective Opening of Epoxides with Alcohols Catalyzed by Ceric(IV) Ammonium Nitrate

Commercially available Ceric(IV) Ammonium Nitrate (CAN) catalyzes nucleophilic ring opening of epoxides in primary, secondary and tertiary alcohols under mild conditions. The corresponding β-alkoxy-alcohols were obtained with high regio and stereoselectivity in high yields.     

Revisiting the Solution Structure of Ceric Ammonium Nitrate

Ceric ammonium nitrate (CAN) is a single‐electron‐transfer reagent with unparalleled utility in organic synthesis, and has emerged as a vital feedstock in diverse chemical industries. Most applications use CAN in solution where it is assigned a monomeric [Ce^IV(NO₃)₆]^2? structure; an assumption traced to half‐century old studies. Using synchrotron X‐rays and Raman spectroscopy we challenge this tradition, converging instead on an oxo‐bridged dinuclear complex, even in strong nitric acid. Thus, one equivalent of CAN is recast as a two‐electron‐transfer reagent and a redox‐activated superbase, raising questions regarding the origins of its reactivity with organic molecules and giving new fundamental insight into the stability of polynuclear complexes of tetravalent ions.     

Ceric Ammonium Nitrate in Organic Synthesis III. A Facile Synthesis of Methoxylated 3, 4 Dihydroisoquinolinium Nitrates

A mild and efficient method for the synthesis of 3, 4-dihydroisoquinolinium salts, key intermediates for the preparation of isoquinoline alkaloïds, by an oxidation of N-methyl-1, 2, 3, 4-tetrahydroisoquinolines using ceric ammonium nitrate (CAN) is described.     

硝酸铈铵中铈的价态分析

讨论了硝酸铈铵中铈的价态分析问题.硫酸亚铁铵法测定样品中的四价铈含量;盐酸羟胺还原四价铈后,EDTA法滴定样品中总铈含量;总铈含量与四价铈含量之差为样品中三价铈含量.     

The Application of Ceric Ammonium Nitrate in the Synthesis of Carbodiazones

The preparation of bisaryl carbodiazone compounds from the aryl substituted carbazides with Ceric Ammonium Nitrate (CAN) has been reported for the first time in excellent yields (80-91%). This method only needs simple instruments and short reaction time. A possible mechanism has been suggested.     

Synthesis of 3-Acyl and 3-Carboalkoxyfurans by the Ceric Ammonium Nitrate Promoted Addition of 1,3-Dicarbonyl Compounds to Vinylic Acetates

3-Acyl- and 3-carboalkoxyfurans can be prepared in 30–55% yield by the oxidative addition of 1,3-dicarbonyl compounds to vinylic acetates induced by eerie ammonium nitrate.     

Graft Copolymerization of (Dimethylamino)Ethyl Methacrylate onto Chitosan Initiated by Ceric Ammonium Nitrate

Abstract

(Dimethylamino)ethyl methacrylate (DMAEMA) was grafted onto chitosan using ceric ammonium nitrate as initiator in acetic acid solution. The effects of reaction variables on the grafting percentage and efficiency percentage were investigated, including the amounts of monomer and initiator, reaction time and reaction temperature. The grafted copolymers were confirmed by FTIR, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The results of TGA and DSC indicated the improvement of thermal stability for chitosan‐g‐poly(PDMAEMA). Solubility test revealed the improved hydrophilicity of grafted chitosan in aqueous acetic acid solution, and its swelled behavior in mixtures of glacial acetic acid and anhydrous ethanol (the ratios of 1:1 and 1:2, v/v). The grafted copolymer possessed amphiphilic structure and exhibited properties of polymeric surfactant.     

Microwave Assisted Catalytic Protection and Deprotection of Alcohols with 3,4-Dihydro-2H-Pyran

Protection of alcohols as their 2-tetrahydropyranyl ethers and their subsequent hydrolysis can be easily achieved through a microwave irradiated reaction catalysed by iodine.     

Conversion of Some Cephalosporins Into the 2-Alkoxy Derivatives Using Alkanolic Ceric (IV) Ammonium Nitrate

A variety of cephalosporins have been converted into the corresponding 2-alkoxy derivatives using ceric ammonium nitrate in the appropriate alcohol.     

Facile Synthesis of 3,3-Di(1H-indol-3-yl)indolin-2-ones Catalyzed by Ceric Ammonium Nitrate (CAN) under Ultrasound Irradiation

Indole fragment is featured widely in a wide variety of pharmacologically and biologically active compounds.[1] The 3,3-bis(3-indolyl)oxindole has been shown to possess antibiotic activities against Escherichia coli, Bacillus subtilis and Staphylococcus aureus. [2] As a continue of our work on the synthesis of indole derivates such as bis(indolyl)methanes,[3]we describe an ultrasound-accelerated reaction of isatin 1 with indoles 2 using a catalytic amount of ceric ammonium nitrate (CAN), which provides an efficient route to the synthesis of 3,3-di(1H-indol-3-yl)indolin-2-ones.     

Oxidative Cyclization of Unsaturated Ketene Dithioacetals with Ceric Ammonium Nitrate to Form Bicyclic Lactones

Ceric ammonium nitrate oxidizes unsaturated ketene dithioacetals in wet MeCN to give cation radicals that cyclize to trisubstituted double bonds and styrenes by cation-like cyclizations leading to cyclic cation radicals that are transformed by further oxidation, hydrolysis and cyclization to bicyclic lactones in moderate to good yield.     

Design,Synthesis and Characterization of 3,4-Dihydro-2H-pyran Containing Copolymer/Clay Nanocomposites

We introduce briefly surface modification of clay minerals, structure, properties and, characterization techniques of polymer-clay (PCN's) nanocomposites. Organically modified layered-silicates or nanoclays have become an attractive class of hybrid materials due to their prospective use in a great variety of applications from industry to health. For design, synthesis and characterization for potential biomedical nanocomposites, antitumor-active copolymer; poly(DHP-alt-MA) were used to prepare copolymer/clay nanocomposites. The functional copolymers, having a combination of rigid/flexible linkages and an ability of complex-formation with interlayered surface of organo-silicate, and their nanocomposites have been synthesized by interlamellar complex-radical copolymerization of intercalated monomer complexes of maleic anhydride (MA) and 3,4-Dihydro-2H-pyran (DHP) with three alkyl ammonium salts surface modified bentonite and monomer mixtures. Poly(DHP-alt-MA) pristine copolymer and poly(DHP-alt-MA)/organically modified bentonite nanocomposites were characterized by Attenuated Total Reflectance-Fourier Transform Infrared Spectroscopy (ATR-FTIR), HR-Raman, X-ray diffraction (XRD) and TEM methods.