The Oxidation of Organic Compounds by Sodium Ruthenate

Lee, Donald G.; Hall, David T.; Cleland, J

doi:10.1139/v72-592

Cited by 33 publications

(10 citation statements)

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“…[5] with respect to time gives eq. [6] from which the initial reaction rate, (dAldt),, can be obtained by setting t = 0.…”

Section: Kinetic Methodsmentioning

confidence: 99%

“…Ruthenate, because it reacts very slowly with carbon-carbon double bonds (I), has found extensive use as a selective oxidant for unsaturated alcohols (2), while permthenate has been used for the oxidative cleavage of carbon-carbon double bonds (3), the oxidation of secondary alcohols to ketones (4), and the conversion of primary alcohols to carboxylic acids (4). Ruthenate also oxidizes saturated secondary alcohols to ketones in good yields (5). Both ions are stable only under basic conditions (6), thus limiting their use as oxidants to organic compounds that are both stable and soluble in aqueous solutions of high pH.…”

Section: Introductionmentioning

confidence: 99%

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Kinetics and mechanism of the oxidation of alcohols by ruthenate and perruthenate ions

Lee¹,

Congson²

1990

Can. J. Chem.

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a number of high valent transition metal ions that can be used as oxidants in organic chemistry. In their reactions with alcohols both ions exhibit several striking similarities -concave Hammett plots, primary deuterium isotope effects, small enthalpies of activation, and large negative entropies of activation. The most likely explanation of the concave upward Haminett plots is the involvement of free radical-like transition states that could be formed by the decomposition of organometallic intermediates.

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“…[5] with respect to time gives eq. [6] from which the initial reaction rate, (dAldt),, can be obtained by setting t = 0.…”

Section: Kinetic Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Kinetics and mechanism of the oxidation of alcohols by ruthenate and perruthenate ions

Lee¹,

Congson²

1990

Can. J. Chem.

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“…Recently, the use of oxocomplexes of ruthenium (RuO 4 2− , RuO 4 − , and RuO 4 ) as homogeneous catalysts for the oxidation of alcohols has become increasingly important because of the necessity of finding economical and environmentally sound conditions for these reactions. Particularly useful in this sense is RuO 4 2− , because this catalytic species participates in such reactions without attacking sensitive linkages in the R group of the alcohol [10,11].…”

Section: Introductionmentioning

confidence: 99%

Kinetic study of the ruthenium(VI)‐catalyzed oxidation of benzyl alcohol by alkaline hexacyanoferrate(III)

Mucientes¹,

Santiago²,

Almena³

et al. 2002

Int J of Chemical Kinetics

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The kinetics of the Ru(VI)-catalyzed oxidation of benzyl alcohol by hexacyanoferrate(III), in an alkaline medium, has been studied using a spectrophotometric technique. The initial rates method was used for the kinetic analysis. The reaction is first order in [Ru(VI)], while the order changes from one to zero for both hexacyanoferrate(III) and benzyl alcohol upon increasing their concentrations. The rate data suggest a reaction mechanism based on a catalytic cycle in which ruthenate oxidizes the substrate through formation of an intermediate complex. This complex decomposes in a reversible step to produce ruthenium(IV), which is reoxidized by hexacyanoferrate(III) in a slow step. The theoretical rate law obtained is in complete agreement with all the experimental observations.

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“…39 The most important synthetic applications of ruthenate, RuO 4 2-, is oxidation of alcohols in alkaline media to carboxylates or ketones. 40 In general, ruthenate does not oxidize alkenes or alkynes at room temperature, for example, oct-7-en-2-ynoic acid was prepared from oct-7-en-2-yn-1-ol in good yield (74%) using a combination of RuCl 3 (1-2 mol%) and potassium persulfate, K 2 S 2 O 8 , in aqueous KOH solution. 41 Osmium(VIII and VI).…”

Section: Short Review Synthesismentioning

confidence: 99%

Direct Oxidation of Primary Alcohols to Carboxylic Acids

Cherepakhin¹,

Williams²

2020

Synthesis

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Oxidation of primary alcohols to carboxylic acids is a fundamental transformation in organic chemistry, yet despite its simplicity, extensive use, and relationship to pH, it remains a subject of active research for synthetic organic chemists. Since 2013, a great number of new methods have emerged that utilize transition-metal compounds as catalysts for acceptorless dehydrogenation of alcohols to carboxylates. The interest in this reaction is explained by its atom economy, which is in accord with the principles of sustainability and green chemistry. Therefore, the methods for the direct synthesis of carboxylic acids from alcohols is ripe for a modern survey, which we provide in this review.1 Introduction2 Thermodynamics of Primary Alcohol Oxidation3 Oxometalate Oxidation4 Transfer Dehydrogenation5 Acceptorless Dehydrogenation6 Electrochemical Methods7 Outlook

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The Oxidation of Organic Compounds by Sodium Ruthenate

Abstract: The preparation of sodium ruthenate and its use as an oxidant for a variety of organic compounds is decribed.

Cited by 33 publications

References 1 publication

Kinetics and mechanism of the oxidation of alcohols by ruthenate and perruthenate ions

Kinetics and mechanism of the oxidation of alcohols by ruthenate and perruthenate ions

Kinetic study of the ruthenium(VI)‐catalyzed oxidation of benzyl alcohol by alkaline hexacyanoferrate(III)

Direct Oxidation of Primary Alcohols to Carboxylic Acids

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