Untitled

Kirsch, André; Lüning, Ulrich; Krüger, Oliver

doi:10.1002/(sici)1521-3897(199910)341:7<649::aid-prac649>3.3.co;2-c

Cited by 6 publications

(7 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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: 97%

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

View full text Add to dashboard Cite

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.

show abstract

Section: Reactive Species Of Nbpmentioning

confidence: 97%

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

View full text Add to dashboard Cite

show abstract

“…In most cases these reagents are converted to phthalimide in the end of reactions, as a nontoxic chemical. It has been reported earlier by several workers [33][34][35][36][37] that NBP is oxidizing and brominating agent because of large polarity of >N-Br bond. NBP is capable f producing Br þ reasonably shows that NBP, like other similar N-halo imides, may exist in various forms in acidic medium, that is, free NBP, protonated NBP, Br þ , HOBr, (H 2 OBr) þ , as per the following equilibria: …”

Section: Mechanismmentioning

confidence: 99%

Catalytic Effect of Cetyltrimethylammonium Bromide on the Oxidation of Oxalic Acid by N-Bromophthalimide in Acidic Medium

Katre

Mudliar

Joshi

et al. 2012

Journal of Dispersion Science and Technology

View full text Add to dashboard Cite

The kinetics of micellar catalyzed oxidation of oxalic acid [OA] by N-bromophthalimide was studied in the presence of perchloric acid at 308 K. The orders of reaction with respect to [Oxalic acid], [oxidant], and [H þ ] were found to be fractional, first and negative fractional order respectively. Cationic micelles of cetyltrimethylammonium bromide increased the reaction rate. The effect of phthalimide, mercuric acetate and inorganic salts, that is, [Cl À ][Br À ] has also been done. The rate reaction decreases with increasing dielectric constant of the medium. The results are treated quantitatively in terms of Piszkiewicz and Berezin models. The rate constant (K obs ), cooperatively index (n), binding constant (k s þ k o ), and corresponding activation parameters (E a , DH # , DS # , and DG # ) were determined. A suitable mechanism consistent with the experimental finding has been proposed.

show abstract

“…Surprisingly, the addition of a carbamate/amide 13–17 or imide 14,18 to an olefin has not been studied at the level of detail relative to other aminohalogination reactions. Swern 22 and others 18–21 previously reported the addition of N -haloamide, N -halocarbamate, N , N -dihaloamide/carbamate, or N -haloimide to an olefin through a radical mechanism to give anti -Markovnikov products. In addition, Heasley 23 and co-workers reported that NBS underwent addition to cyclohexene, in the presence of 1 equiv of BF 3 ·OEt 2 , to yield the trans -1-bromo,2- N -succinimide stereoisomer adduct.…”

Section: Introductionmentioning

confidence: 99%

Hydroxyamination of Olefins Using Br-N-(CO₂Me)₂

et al. 2015

View full text Add to dashboard Cite

The hydroxyamination reagent Br-N-(CO2Me)2 underwent Markovnikov addition to various olefins in the presence of catalytic BF3·OEt2 and provides efficient access to aminoalcohols. The reaction provided the trans-1-bromo, 2-N-bis-carbamate adduct stereoisomer in all cases. The resulting adduct underwent cyclization to give an oxazolidinone, which could be readily hydrolyzed to an oxazolidin-2-one or an amino alcohol.

show abstract

Untitled

Cited by 6 publications

References 0 publications

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

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

Catalytic Effect of Cetyltrimethylammonium Bromide on the Oxidation of Oxalic Acid by N-Bromophthalimide in Acidic Medium

Hydroxyamination of Olefins Using Br-N-(CO₂Me)₂

Contact Info

Product

Resources

About

Untitled

Cited by 6 publications

References 0 publications

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

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

Catalytic Effect of Cetyltrimethylammonium Bromide on the Oxidation of Oxalic Acid by N-Bromophthalimide in Acidic Medium

Hydroxyamination of Olefins Using Br-N-(CO2Me)2

Contact Info

Product

Resources

About

Hydroxyamination of Olefins Using Br-N-(CO₂Me)₂