Facile regeneration of carbonyl compounds from oximes under microwave irradiations using N-bromophthalimide

Khazaei, Ardeshir; Manesh, Abbas Amini

doi:10.1590/s0103-50532005000500030

Cited by 20 publications

(8 citation statements)

References 9 publications

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“…It has been reported earlier by several workers [30][31][32][33][34][35][36][37][38] that NBP is good oxidizing and brominating agent because of the highly polar N-Br bond. NBP, like other similar N-halo imides, may exist in various forms in acidic medium, i.e., free NBP, protonated NBP, Br ?…”

Section: Discussionmentioning

confidence: 99%

Kinetics and mechanism of oxidation of β-Alanine by N-bromophthalimide in the presence of Ru(III) chloride as homogenous catalyst in acidic medium

Singh¹,

Jain²,

Negi³

et al. 2009

Transition Met Chem

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The kinetics of Ru(III) chloride-catalyzed oxidation of b-Alanine (NH 3 ? CH 2 CH 2 COOH, b-Ala) by Nbromophthalimide (NBP) in aqueous perchloric acid medium was studied at 35°C. The rate law followed a first-order and zero-order dependence with respect to [NBP] and [b-Ala], respectively. The reaction followed first-order kinetics with respect to [Ru(III)] chloride at a range of low concentrations while the order changed from first-to zero-order at high concentration of [Ru(III)] chloride; demonstrating the catalytic effect for the oxidation of b-Ala by NBP. The rate decreased with increase in acidity. Chloride ions positively influenced the rate of the reaction. Neither phthalimide (NHP) nor Hg(II) influenced the reaction rate. Ionic strength (I) and dielectric constant (D) of the medium had no significant effect on the rate. Activation parameters of the reactions were determined by studying the reaction at different temperatures (30-50°C). The colorimetric, FTIR, and GC-MS techniques were used to identify methyl cyanide (CH 3 CN) and CO 2 as products of the reaction. In the reaction, approximately 2.3 moles of NBP oxidized one mole of b-Ala. A reaction scheme of the oxidation of b-Ala by NBP in the presence of Ru(III) chloride was found to be in consistent with the rate law and the reaction stoichiometry.

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Section: Discussionmentioning

confidence: 99%

Kinetics and mechanism of oxidation of β-Alanine by N-bromophthalimide in the presence of Ru(III) chloride as homogenous catalyst in acidic medium

Singh¹,

Jain²,

Negi³

et al. 2009

Transition Met Chem

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“…Similar reactions were also carried out under microwave irradiation in very short times [193]. NBP has been used for the oxidation of various organic compounds in the presence of mercuric acetate as well as in acetic acid medium.…”

Section: Scheme 148mentioning

confidence: 99%

Application of N-halo reagents in organic synthesis

Kolvari

Ghorbani‐Choghamarani

Salehi

et al. 2007

JICS

157

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This review article summarizes published data on the application of N-halo reagents (such as N-halo amines, N-halo amides and/or imides, N-halo sulfonamides and/or imides, and etc.) in various organic functional group transformations such as: oxidation reactions, deprotection and protection of different functional groups, halogenation of saturated and unsaturated compounds, acylation of alcohols, phenols, amines or thiols, epoxidation of alkenes, aziridination and etc. The main purpose of writing this review is encouraging of active researchers interested to this field for the synthesis of new N-halo reagents specially with different halogens and applications of these new N-halo reagents in organic reactions or finding more and more applications of existing N-halo reagents in organic synthesis.

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“…It has been reported earlier by several workers [28][29][30][31][32] that NBP is a good oxidizing and brominating agent because of the large polarity of the [N-Br bond. NBP, like other similar N-halo imides, may exist in various forms in acidic medium, i.e., free NBP, protonated NBP, Br ?…”

Section: Reactive Species Of Nbpmentioning

confidence: 98%

Oxidation of d-glucose by N-bromophthalimide in the presence of chlorocomplex of iridium(III): a kinetic and mechanistic study

Singh¹,

Sachdev

Shrivastava³

et al. 2011

Res Chem Intermed

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The kinetics of Iridium (III) catalyzed oxidation of D-glucose [D-glu] has been studied by N-bromophthalimide [NBP] in the acidic medium (pH 1.3) at 303 K. The reaction followed first-order kinetics with respect to [NBP] from 0.5 9 10 -4 to 4.0 9 10 -4 mol dm -3 . The results indicate the first-order kinetics in [iridium(III)] chloride at lower concentrations from 0.75 9 10 -6 to 5.8 9 10 -6 mol dm -3 tends towards a zero order at its higher concentrations (up to 13.36 9 10 -6 mol dm -3 ). Zero-order kinetics with respect to [D-glu] from 2.0 9 10 -3 to 20.0 9 10 -3 mol dm -3 was observed throughout its variation. A positive effect on the oxidation rate was observed for [Cl -] from 0.2 9 10 -5 to 2.4 9 10 -5 mol dm -3 and the rate of reaction decreased with increase in dielectric constant (decreasing acetic acid from 35 to 15%) of the medium. A negative effect was observed on the reaction rate for [H ? ] from 1.5 9 10 -2 to 12.0 9 10 -2 mol dm -3 . Addition of reduced product of oxidant, i.e., phthalimide from 1.0 9 10 -4 to 8.0 9 10 -4 mol dm -3 did not show a significant effect on the oxidation velocity. Rate of reaction increased with increase in ionic strength from 0.2 9 10 -1 to 4.0 9 10 -1 mol dm -3 of the medium, i.e., increase in [KNO 3 ]; the rate of reaction was increased. From the linear Arrhenius plot of log k 1 versus 1/T, the activation energy (Ea = 50.91 kJ mol -1 ) was calculated. With the help of the energy of activation, parameters such as enthalpy of activation (DH # = 48.39 kJ mol -1 ), entropy of activation (DS # = -321.63 JK mol -1 ), Gibbs free energy of activation (DG # = 145.84 kJ mol -1 ) and frequency factor (Log A = -3.97) were also calculated. A suitable mechanism in conformity with kinetic observations was proposed to explain reaction stoichiometry and product analysis.

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Facile regeneration of carbonyl compounds from oximes under microwave irradiations using N-bromophthalimide

Cited by 20 publications

References 9 publications

Kinetics and mechanism of oxidation of β-Alanine by N-bromophthalimide in the presence of Ru(III) chloride as homogenous catalyst in acidic medium

Kinetics and mechanism of oxidation of β-Alanine by N-bromophthalimide in the presence of Ru(III) chloride as homogenous catalyst in acidic medium

Application of N-halo reagents in organic synthesis

Oxidation of d-glucose by N-bromophthalimide in the presence of chlorocomplex of iridium(III): a kinetic and mechanistic study

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