Convenient,Mild Catalytic Deprotection of Oximes to Carbonyl Compounds with Hydrogen Peroxide and Iodine Catalyst in Aqueous Acetonitrile

A clean, mild, and efficient catalytic deoximation procedure compatible with several common functional groups has been developed using 30% hydrogen peroxide activated by iodine catalyst in aqueous acetonitrile under essentially neutral conditions. The mechanistic features of an iodonium ion–driven nucleophilic cleavage of oximic C[dbnd]N have been revealed.     

Catalytic Oxidation of Furan and Hydrofuran Compounds. 8. Conversions of 2(5H)-Furanone by Hydrogen Peroxide in Media of Various pH

The reaction of 2(5H)-furanone with aqueous hydrogen peroxide in media of pH within the range 1-8 have been studied in the absence of catalysts for the first time. It was discovered that at pH 3 to 8 2(5H)-furanone was almost quantitatively converted into succinic acid and reduction of the acidity of the medium facilitates the reaction. A possible scheme is considered for the conversions of 2(5H)-furanone under the reaction conditions.     

Simple and Friendly Sulfones Synthesis Using Aqueous Hydrogen Peroxide with a Reusable Keggin Molybdenum Heteropolyacid,Immobilized on Aminopropyl-Functionalized Silica

Keggin molybdenum heteropolyacid (H₃PMo₁₂O₄₀), immobilized on aminopropyl-functionalized silica catalysts, were made using two immobilization methods: incipient wetness and equilibrium adsorption. The material prepared for the equilibrium adsorption technique was found to be a highly efficient, ecofriendly, and recyclable heterogeneous catalyst for the selective oxidation of sulfides to sulfones in excellent yields, under mild reaction condition using 35% w/v aqueous hydrogen peroxide as the oxidant.     

Flow Injection Analysis of Benzoyl Peroxide Using N,N,N,N-Tetramethyl-p-phenylenediamine (TMPDA) and Surfactants

Abstract

The flow injection analysis of benzoyl peroxide using N,N,N,N-tetramethyl-p-phenylenediamine (TMPDA, also known as Wurster's reagent) and a solvent system including the surfactant sodium dodecyl sulfate (SDS) and cerium(IV) as a catalyst at pH 6.0 at 612 nm was investigated. The method was applied to the analysis of acne cream and flour. The study included a 26-metal-ion search for other possible methods of catalysis and a buffer study of SDS and cetyltrimethyl ammonium bromide (CTAB).     

2-Phenyl-2-(2-pyridyl)imidazolidine (PPI) as New Catalyst in the Efficient,Mild, and Regioselective Conversion of Epoxides to Thiocyanohydrines with Ammonium Thiocyanate

2-Phenyl-2-(2-pyridyl)imidazolidine (PPI) catalysis the addition of thiocyanate ion to epoxides to afford g -hydroxy thiocyanate in high yields, mild conditions, and regioselectivity. Thus, several 2-hydroxyethyl thiocyanates, which are useful intermediates toward biological active molecules, are obtained easily in very good yields.     

Automated Determination of Hydrogen Peroxide at the Micro-Molar Level in Rainwater and Snow Using a Stopped-Flow Approach in a Hybrid Sequential Injection/Flow Injection Manifold

A new automated method is reported for the determination of H₂O₂ in real samples. The method is based on the quenching effect of the analyte on the reaction between tris(2-carboxyethyl)phosphine (TCEP) and Ellman's reagent (DTNB). All necessary steps were accomplished under flow conditions using a hybrid sequential injection (SI)/flow injection (FI) setup. The sensitivity was enhanced by applying a stopped-flow step (120 s) in order to promote the reaction between H₂O₂ and TCEP. The proposed analytical protocol was validated for linearity (10–75 µmol L^?1), limits of detection (c _L = 1.0 µmol L^?1), quantitation (c _Q = 3.3 µmol L^?1), precision (s _r = 1.3–1.7%), accuracy, and selectivity. It was then applied successfully to the analysis of H₂O₂ in spiked rainwater and snow samples.     

Catalytic Oxidation of Furan and Hydrofuran Compounds. 7. Production of 2(5H)-Furanone by Oxidation of Furfural with Hydrogen Peroxide and Some of Its Transformations in Aqueous Solutions

Data on the synthesis of 2(5H)-furanone by the oxidation of furfural with aqueous hydrogen peroxide under the conditions of autocatalysis by the accumulating acids and also in the presence of catalytic amounts of Cr(VI) and Mo(VI) compounds are presented. Some transformations of 2(5H)-furanone in aqueous solutions are studied: hydrolysis, oxidation by potassium permanganate, complex formation with the ions of certain d-metals.     

Versatile Methodology to Hydrate Alkynes,in the Presence of a Wide Variety of Functional Groups,with Mercury(II) p-Toluensulfonamidate,Under Catalytic,Mild, and Neutral Conditions

A method to generate carbonylic compounds from alkynes under mild and neutral conditions, with excellent functional group compatibility and good yields, is described. Hydration takes place under catalytic conditions by using 0.1 to 0.2 equivalents of the easily available and inexpensive mercury(II) p-toluensulfonamidate in a hydroalcoholic solution. After use, the catalyst is rendered inert and/or recycled.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.