Oxidation of primary, secondary, and tertiary amines with neutral permanganate. Simple method for degrading amines to aldehydes and ketones

Rawalay, Surjan S.; Shechter, Harold

doi:10.1021/jo01285a042

Cited by 98 publications

(50 citation statements)

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“…[7]) is quite similar to those reported for the oxidation of dimethylamine (3) and of trimethylamine (2) by permanganate.…”

Section: Discussionsupporting

confidence: 87%

“…Equation [7] is in full agreement with the kinetic orders found for the oxidizing and reducing agents in the noncatalytic pathway (see eq. [2] and Fig.…”

Section: Discussionsupporting

confidence: 82%

“…5 shows that the noncatalytic mechanism is first-order dependent on the hydroxyl ion concentration, as required by eq. [7]. Although the existence of an intercept different from zero suggests that the protonated form of the amine also has some reactivity toward permanganate ion, the small magnitude of that intercept indicates that this other modality of reaction is of very minor importance, the predominant oxidation being that of free methylamine by permanganate ion (see eq.…”

Section: Discussionmentioning

confidence: 99%

“…On the other hand, the products from the oxidation of a wide variety of amines by permanganate ion are known (5)(6)(7).…”

Section: Introductionmentioning

confidence: 99%

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Kinetics and mechanisms of oxidation of methylamine by permanganate ion

Mata-Pérez¹,

Perez‐Benito²

1987

Can. J. Chem.

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. Can. J. Chem. 65, 2373 (1987). The oxidation of methylamine by permanganate ion in aqueous phosphate buffers is autocatalyzed by a soluble form of colloidal manganese dioxide temporarily stabilized in solution by adsorption of phosphate ions on its surface. The dependence of the rate constants of both the noncatalytic and catalytic mechanisms on the concentrations of both methylammonium and hydroxyl ions and on temperature has been determined. The activation parameters have been obtained. Mechanisms in agreement with the experimental data are proposed.FERNANDO MATA-PEREZ et JOAQUIN F. PEREZ-BENITO. Can. J. Chem. 65, 2373 (1987). L'oxydation de la mithylamine par l'ion permanganate, en solution dans des tampons de phosphates, est autocatalyste par une forme soluble du bioxyde de manganese colloidal qui est temporairement stabiliste en solution par adsorption des ions phosphates sur sa surface. On a dttermini les relations qui existent entre les constantes de vitesse, tant des micanismes catalysis que ceux des mtcanismes non-catalysts, et soit les concentrations tant des ions mithylammonium que des ions hydroxyles soit la temptrature. On a obtenu les paramttres d'activation. On propose des micanismes qui sont en accord avec les donntes expirimentales.[Traduit par la revue]

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“…[7]) is quite similar to those reported for the oxidation of dimethylamine (3) and of trimethylamine (2) by permanganate.…”

Section: Discussionsupporting

confidence: 87%

“…Equation [7] is in full agreement with the kinetic orders found for the oxidizing and reducing agents in the noncatalytic pathway (see eq. [2] and Fig.…”

Section: Discussionsupporting

confidence: 82%

Section: Discussionmentioning

confidence: 99%

“…On the other hand, the products from the oxidation of a wide variety of amines by permanganate ion are known (5)(6)(7).…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Kinetics and mechanisms of oxidation of methylamine by permanganate ion

Mata-Pérez¹,

Perez‐Benito²

1987

Can. J. Chem.

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“…HOWmined (7)(8)(9), and some kinetic studies of the permanganate ion ever, a 2.5-fold increase in the concentration of the buffer oxidation of trimethylamine in phosphate buffers have been substances (all the other experimental conditions remaining published (10, 1 I), no identification of the soluble brownconstant) led to the observation of a sharp isosbestic point at yellow product has been reported. The present paper aims to 470 nm (see Fig.…”

Section: No Isosbestic Point Wasmentioning

confidence: 99%

Identification of the product from the reduction of permanganate ion by trimethylamine in aqueous phosphate buffers

Mata-Pérez¹,

Perez‐Benito²

1985

Can. J. Chem.

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The product obtained from the reduction of potassium permanganate by trimethylamine in aqueous phosphate buffers has been identified as a soluble form of colloidal manganese dioxide which is stabilized in solution by adsorption of phosphate ions on its surface. The dependence of the rate of flocculation on several experimental variables has been studied. Phosphate ions have been found to increase the solubility of the colloid by increasing the apparent energy of activation of the flocculation process. This could explain the well-known capacity of those ions for retarding the precipitation of manganese dioxide.

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