Kinetics and mechanism of bromamine-T oxidation of some cyclic ketones in acidic media

Singh, B.; Chand, Rajendra

doi:10.1016/s0040-4020(01)96607-4

Cited by 8 publications

(5 citation statements)

References 11 publications

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“…Singh et al carried out a kinetic study based on the oxidation of cyclopentanone and cyclohexanone using bromamine-T in perchloric acid media (Scheme 29). 54 The rate shows a zeroorder dependence on [BAT] and a first-order dependence on both [ketones] and [H + ]. The kinetics of the reaction was unaffected by the variation of the ionic strength of the medium and by the addition of p-toluenesulfonamide.…”

Section: Scheme 28 Oxidation Of Dimethyl Sulfoxide By Bromamine-t In ...mentioning

confidence: 97%

“…In the D2O medium, the rate increased, and an inverse solventisotope effect was observed with k′ (D2O)/k′ (H2O) = 1.60. 54). 79 Their study revealed that oxidation obeys identical kinetics with a first-order dependence on each [oxidant] and [INH] and an inverse fractional-order dependence on [ -OH] was recorded.…”

Section: Scheme 50 Oxidation Of Cysteine By Bromamine-tmentioning

confidence: 99%

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Bromamine-T (TsNBrNa): A Biologically Significant, Versatile Bromo-Organic Reagent

Kashyap¹,

Phukan²

2023

Synlett

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Bromamine-T (BAT) is a distinguished member of a special class of compounds called organic haloamines, possessing oxidising properties. It can act as the source of halonium ions, hypohalite species, and N-anions, along with the display of basic as well as nucleophilic properties. Bromamine-T finds wide application as an efficient reagent for various organic transformations such as aminobromination, amination, oxidation etc., under mild conditions with minimum toxicity. Moreover, due to its immense biological significance, this reagent is piquing the interest of numerous researchers.

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Section: Scheme 28 Oxidation Of Dimethyl Sulfoxide By Bromamine-t In ...mentioning

confidence: 97%

Section: Scheme 50 Oxidation Of Cysteine By Bromamine-tmentioning

confidence: 99%

Bromamine-T (TsNBrNa): A Biologically Significant, Versatile Bromo-Organic Reagent

Kashyap¹,

Phukan²

2023

Synlett

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“…The kinetics and mechanism of the oxidation of cyclopentanone and cyclohexanone to the corresponding 1,2-diketones with bromoamine-T (4-MeC 6 H 4 SO 2 NNaBr) in acidic media was studied. 39 Enolisation of the starting ketones was found to be the limiting step of the oxidation.…”

Section: Homentioning

confidence: 99%

Oxidative methods in the synthesis of vicinal di- and polycarbonyl compounds

Филимонов¹,

Yusubov²,

Chi³

1998

Russ. Chem. Rev.

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“…Bromamine-T (BAT, sodium salt of N-bromo-p-toluenesulphonamide) is a low molecular weight organic compound with an oxidizing effect, often used in oxidation reactions of, among others, alcohols, aldehydes, ketones and amines [1][2][3][4][5]. Contemporary studies using BAT mainly concern the examination of drugs oxidation mechanisms in biological systems (drugs used, for instance, in the treatment of allergies and diabetes) [6][7][8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

A macromolecular N-bromosulphonamide as a heterogeneous oxidant in acidic media

Ciechanowska

Kociołek‐Balawejder

2015

Polym. Bull.

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Styrene-divinylbenzene copolymer containing N-bromosulphonamide groups as sodium salt, [P]-SO 2 NBrNa, can be viewed as a high molecular weight redox polymer mimicking its low molecular weight analogue: Bromamine-T. The stability of this copolymer in acidic media has not been studied in detail to date. This paper reports on studies of the reaction between the copolymer and aqueous FeSO 4 solution conducted in a series of batch and column experiments. It was found that pH \3.0 results in transition of active bromine from -SO 2 NBr -groups to the solution, followed by oxidation of Fe 2? ions to Fe 3? ions by elemental bromine. In reaction media of pH [3.0, active bromine remains bound to the functional groups, facilitating application of this copolymer as an effective oxidant in column processes running in weakly acidic reaction media. Results of the present work provide evidence that -SO 2 NBr -functional groups of the copolymer can stably exist in acidic form which is in contrast to the behaviour of the low molecular weight analogue (N-bromo-p-toluenesulphonic acid does not occur as a pure chemical compound).

show abstract

Kinetics and mechanism of bromamine-T oxidation of some cyclic ketones in acidic media

Cited by 8 publications

References 11 publications

Bromamine-T (TsNBrNa): A Biologically Significant, Versatile Bromo-Organic Reagent

Bromamine-T (TsNBrNa): A Biologically Significant, Versatile Bromo-Organic Reagent

Oxidative methods in the synthesis of vicinal di- and polycarbonyl compounds

A macromolecular N-bromosulphonamide as a heterogeneous oxidant in acidic media

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