Synthetic Applications of Oxone<sup>®</sup>

He, Wei

doi:10.1055/s-2006-951565

Cited by 8 publications

(5 citation statements)

References 10 publications

(15 reference statements)

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“…[42] Oxone is applied directly during the synthesis to convert the alkene into the dibromide (entry 21, [42] entry 22 [43] ), but also to regenerate the reagent, which is a carrying agent (entry 10b), [29] an N-halo compound (entry 23), [44,45] or another N-halo compound, Nbromsuccinimide (NBS, entry 24). [46] Overviews of applications of the oxidants sodium perborate, [50][51][52] CAN, [53][54][55][56] Selectfluor [57,58] and other N-halo reagents, [59] sodium periodate, [60] DIB as a polyvalent iodine compound [61][62][63][64] and Oxone [65,66] can be found in the litera- ture. Special protocols such as enantioselective bromination reactions, [67] the application of a CuBr 2 /LiBr-system [68] or special polymer supports [32] have not been considered here.…”

Section: Resultsmentioning

confidence: 99%

“…Overviews of applications of the oxidants sodium perborate,50–52 CAN,53–56 Selectfluor®57, 58 and other N ‐halo reagents,59 sodium periodate,60 DIB as a polyvalent iodine compound61–64 and Oxone®65, 66 can be found in the literature. Special protocols such as enantioselective bromination reactions,67 the application of a CuBr 2 /LiBr‐system68 or special polymer supports32 have not been considered here.…”

Section: Resultsmentioning

confidence: 99%

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Electrophilic Bromination of Alkenes: Environmental, Health and Safety Aspects of New Alternative Methods

Eissen

Lenoir

2008

Chemistry A European J

103

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More than twenty new alternative methods for bromination of alkenes have been evaluated taking into consideration their resource demands, waste production as well as environmental, health and safety aspects. The cost of bromine and the substances designated to circumvent the application of molecular bromine have also been taken into account. As bromine is only one of several problematic substances being used, its avoidance-by applying bromine supported on solid material or by performing the in situ generation of bromine-does not significantly reduce the technological requirements. On the contrary, the resource demands and amount of waste produced by most new methods are significantly higher compared to the standard methods, especially if the recycling of a carrying agent is not efficient. The method using hydrobromic acid and hydrogen peroxide can be regarded as a competitive alternative to the standard method. The application of certain carrying agents could be interesting, because solvents such as carbon tetrachloride or chloroform used during synthesis could be replaced with less problematic ones during work-up. However, problems associated with these alternatives are not resolved as yet.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Electrophilic Bromination of Alkenes: Environmental, Health and Safety Aspects of New Alternative Methods

Eissen

Lenoir

2008

Chemistry A European J

103

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“…Indoxacarb‐rich agricultural soils samples used to screen bacteria with hydrolytic activity were collected from various places of Zhejiang, Anhui, and Henan Provinces, China. ( R , S )‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1 H ‐indene‐2‐carboxylic acid methyl ester (98%) was prepared from 5‐chloro‐1‐indanone in our laboratory, according to reported procedures . All chemicals used were analytical reagents.…”

Section: Methodsmentioning

confidence: 99%

“…(R,S)-5-chloro-1-oxo-2,3-dihydro-2-hydroxy-1Hindene-2-carboxylic acid methyl ester (98%) was prepared from 5-chloro-1-indanone in our laboratory, according to reported procedures. [29][30][31] All chemicals used were analytical reagents.…”

Section: Generalmentioning

confidence: 99%

Whole‐cell biocatalytic of Bacillus cereus WZZ006 strain to synthesis of indoxacarb intermediate: (S)‐5‐Chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester

Zhang

Cheng

et al. 2019

Chirality

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In this study, a newly isolated strain screened from the indoxacarb‐rich agricultural soils, Bacillus cereus WZZ006, has a high stereoselectivity to racemic substrate 5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester. (S)‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester was obtained by bio‐enzymatic resolution. After the 36‐hour hydrolysis in 50‐mM racemic substrate under the optimized reaction conditions, the e.e.s was up to 93.0% and the conversion was nearly 53.0% with the E being 35.0. Therefore, B cereus WZZ006 performed high‐level ability to produce (S)‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester. This study demonstrates a new biocatalytic process route for preparing the indoxacarb chiral intermediates and provides a theoretical basis for the application of new insecticides in agricultural production.

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“…Overviews of applications of the oxidants sodium perborate − , CAN − , Selectfluor , and other N-halo reagents , sodium periodate , DIB as polyvalent iodine compound − , and Oxone , can be found in the literature.…”

Section: Exercisesmentioning

confidence: 99%

Oxidation Numbers, Oxidants, and Redox Reactions: Variants of the Electrophilic Bromination of Alkenes and Variants of the Application of Oxone

et al. 2010

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Oxidation-state and donor−acceptor concepts are important areas in the chemical education. Student worksheets containing problems that emphasize oxidation numbers, redox reactions of organic compounds, and stoichiometric reaction equations are presented. All of the examples are incorporated under one unifying topic: the production of vicinal dibromides. Recent synthetic approaches use redox systems to generate bromine in situ to minimize hazards associated with molecular bromine. They illustrate how a range of oxidants can be applied to brominate the alkenes. The oxidant Oxone, also called Caroat or Curox, is examined. In addition to the solutions, the worksheets contain supporting information to help the students solve the problems. Thus, students are able to work independently with the material.

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Synthetic Applications of Oxone^®

Cited by 8 publications

References 10 publications

Electrophilic Bromination of Alkenes: Environmental, Health and Safety Aspects of New Alternative Methods

Electrophilic Bromination of Alkenes: Environmental, Health and Safety Aspects of New Alternative Methods

Whole‐cell biocatalytic of Bacillus cereus WZZ006 strain to synthesis of indoxacarb intermediate: (S)‐5‐Chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester

Oxidation Numbers, Oxidants, and Redox Reactions: Variants of the Electrophilic Bromination of Alkenes and Variants of the Application of Oxone

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Synthetic Applications of Oxone®

Cited by 8 publications

References 10 publications

Electrophilic Bromination of Alkenes: Environmental, Health and Safety Aspects of New Alternative Methods

Electrophilic Bromination of Alkenes: Environmental, Health and Safety Aspects of New Alternative Methods

Whole‐cell biocatalytic of Bacillus cereus WZZ006 strain to synthesis of indoxacarb intermediate: (S)‐5‐Chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester

Oxidation Numbers, Oxidants, and Redox Reactions: Variants of the Electrophilic Bromination of Alkenes and Variants of the Application of Oxone

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Synthetic Applications of Oxone^®