Simple and economical conversion of organic compounds with H₂O₂ catalyzed by ruthenium (III) chloride

Abstract

Six aromatic aldehydes, two hydrocarbons, one cycloalcohol and one aromatic alcohol, viz. benzaldehyde, p-chlorobenzaldehyde, cinnamaldehyde, 4-methoxybenzaldehyde, o-hydroxybenzaldehyde, 4-hydroxy, 3-methoxybenzaldehyde, anthracene, phenanthrene, cyclohexanol and benzyl alcohol dissolved in acetic acid, were oxidized in quantitative to moderate yields by 50% H 2 O 2 in the presence of traces of RuCl 3 (substrate : catalyst ratio 85 400 to 387 500 : 1). Conditions for highest yields, under most economical conditions, were obtained. Higher catalyst concentrations decreased the yield. Oxidation in aromatic aldehydes is selective at aldehydic group only, and other groups remain unaffected. The extent of oxidation in phenanthrene depends on temperature or the relative amount of substrate or both. In this new, simple and economical method, which is environmentally safe and requires less time, oxocentered carboxylate species of ruthenium (III) probably catalyze the oxidation.

A kinetic and mechanistic study of the osmium(VIII)-catalysed oxidation of crotyl alcohol by hexacyanoferrate(III) in aqueous Alkaline medium

“…However, reactions in alkaline medium [1][2][3][4][5][6][7][8] are not fast probably due to the reduced oxidation potential of the [Fe(CN) 6 ] 3− /[Fe(CN) 6 ] 4− redox couple. 9 It is for this reason that a large number of transition metal ions such as Os(VIII), [10][11][12][13] Ru(III), [14][15][16][17] Ru(VI), 18 Ru(IV), 19 Rh(III), 20 Ir(III), 21 Ru(VIII) 22 and Pd(II) 23,24 have been employed as catalysts in alkaline medium. A large number of Os(VIII)-catalysed oxidations of both organic [25][26][27][28][29][30] and inorganic [31][32][33] compounds with hexacyanoferrate(III) in alkaline media have been reported.…”

Synthesis of Anthraquinones by Iridium-Catalyzed [2 + 2 + 2] Cycloaddition of a 1,2-Bis(propiolyl)benzene Derivative with Alkynes

“…Moreover, anthraquinones have been widely used as catalysts for producing hydrogen peroxide [15], dyes for fibers [16,17] and cells [18], a digestion catalyst for wood [19], and chemical sensors [20]. Thus, the development of synthetic methods for the formation of multi-substituted anthraquinones is an important research topic, and several synthtic methods including the oxidation of anthracene [21,22], the Friedel-Crafts reaction of phthalic anhydride [23], and the Diels-Alder reaction of naphthoquinones followed by aromatization [24] have been developed.…”

Oxidation of Vicinal Diols by Cerium(IV) in Aqueous Acidic Media Catalyzed by Rhodium(III)

“…We have also reported the oxidation of cyclic ketones by alkaline hexacyanoferrate(III) catalyzed by rhodium(III) chloride, in which it was observed that the catalytically active species of rhodium(III) depends on the pH of the medium [6,7]. We have also compared the catalytic activity of rhodium(III) chloride with iridium(III) and palladium(II) in the oxidation of various organic compounds with hydrogen peroxide from the synthetic point of view and it was observed that rhodium(III) is quite effective in catalyzing the such as organic oxidations [8]. To find out the potential of rhodium(III) chloride in catalyzing the oxidation of vicinal diols with cerium(IV) sulfate, in aqueous sulfuric acid medium, and to confirm whether scission of C-H takes place or it is the C-C bond which is broken during the course of oxidation, we have studied the oxidation of two vicinal diols viz.…”