A New Application of N-Bromosaccharin as a Selective and Efficient Oxidative Reagent for Regeneration of Carbonyl Compounds From Oximes

Khazaei, Ardeshir; Manesh, Abbas Amini; Rostami, Amin

doi:10.1080/10426500490485471

Cited by 17 publications

(10 citation statements)

References 11 publications

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“…1,3-Dibromo-5,5-dimethylhydantoin (DBH, 6) with the commonly used trade name Brom-55, is a cream to palebrown powder which melts at [186][187][188][189][190][191][192] ºC. This reagent is sparingly soluble in carbon tetrachloride, benzene and water (0.06%, 1.1%, and 0.1% at 20 ºC, respectively).…”

Section: 3-dibromo-55-dimethylhydantoinmentioning

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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Section: 3-dibromo-55-dimethylhydantoinmentioning

confidence: 99%

Application of N-halo reagents in organic synthesis

Kolvari

Ghorbani‐Choghamarani

Salehi

et al. 2007

JICS

157

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“…8 These novel reagents have advantages over the conventional homogeneous solution techniques, such as: easy set-up and work-up, mild experimental condition, and high yield and selectivity . [9][10] During the course of our systematic study on oxidation of organic compounds , [11][12][13][14][15][16][17] we report herein an oxidation of alcohols to the carbonyl compounds with Thallium (Ш) Nitrate (TTN) supported on Silica gel catalyzed by AlCl 3 in solution, scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Silica Supported Thallium (Iii) Nitrate: An Effective Oxidant for Oxidation of Alcohols to the Carbonyl Compounds

Manesh

Nazari

2015

J. Chil. Chem. Soc.

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Thallium (III) Nitrate Supported on Silica gel was found to be an efficient reagent system for oxidation of primary and secondary alcohols to their corresponding carbonyl compounds under mild conditions. The striking features of our method are: short reaction times, formation of no over oxidation products due to high selectivity and mild nature of oxidant, easy work-up procedure, high yields and carbon carbon double or triple bond functional group in the alcohol structure does not oxidize to other group.

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“…), N-haloamides [12][13][14] (N-haloacetamides, N-bromobenzamide, N-chloronicotinamide, etc. ), N-halosaccharins [15][16][17] and N-bromophthalimide 18,19 are commonly used for the oxidation of various organic compounds such as alcohols, aldehydes, amino acids, keto acids, sulphides, etc. However, no detailed kinetic study of oxidation of (phenylthio)acetic acid with N-bromophthalimide has so far been attempted.…”

Section: Introductionmentioning

confidence: 99%

Mechanism of Oxidation of (p‐Substituted Phenylthio)acetic Acids with N‐Bromophthalimide

Alhaji¹,

Mohideen²,

Kalaimathi³

2010

Journal of Chemistry

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The kinetics of oxidation of (phenylthio)acetic acid (PTAA) byN-Bromophthalimide (NBP) in acetonitrile-water solvent mixture at 298 K in the presence of perchloric acid has been followed potentiometrically. The reaction is first-order each in NBP and PTAA and inverse fractional-order in H+. Also, it has been found that the reaction rate is not affected by changes in ionic strength of the reaction medium or by the addition of chemicals such as phthalimide, acrylonitrile and potassium bromide. However, an increase in the water content of the solvent mixture causes an increase in the rate of reaction. These observations have been well analyzed in favour of a SN2-type mechanism, involving NBP itself as the reactive species. Effect of substituents on the reaction rate has been analysed by employing various (p-sustituted phenylthio)acetic acids. The electron-releasing substituent in the phenyl ring of PTAA accelerates the reaction rate while the electron-withdrawing substituent retards the rate. The excellently linear Hammett plot yields a large negative ρ value, supporting the involvement a bromosulphonium ion intermediate in the rate-determining step.

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A New Application of N-Bromosaccharin as a Selective and Efficient Oxidative Reagent for Regeneration of Carbonyl Compounds From Oximes

Cited by 17 publications

References 11 publications

Application of N-halo reagents in organic synthesis

Application of N-halo reagents in organic synthesis

Silica Supported Thallium (Iii) Nitrate: An Effective Oxidant for Oxidation of Alcohols to the Carbonyl Compounds

Mechanism of Oxidation of (p‐Substituted Phenylthio)acetic Acids with N‐Bromophthalimide

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