Some Reactions with N-Bromosuccinimide

Barakat, M. Z.; El-Wahab, Mohamed Fathy Abd; El-Sadr, M. M.

doi:10.1021/ja01611a077

Cited by 33 publications

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“…8 The product readily condensed with the aminoester 5 to give azodiester 4a. This was more conveniently made by manganese(IV) oxide oxidation of 5 in benzene using the method of Bakalat et al 9 Although the yield was poor, and attempts to improve it by using other solvents were not successful, the conversion was good and the reaction was very clean so that recovered 5 could be recycled. The aminoester 5 could also be oxidised to 4a using iodosobenzene diacetate, lead (IV) acetate or potassium permanganate/copper sulfate but yields were also poor and the reactions were not clean.…”

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confidence: 99%

3,3′-Azothiophene

Glover

Huddleston

Wood

2013

Journal of Chemical Research

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Methyl 3-nitrothiophene-2-carboxylate was reduced with bismuth(III) chloride/potassium borohydride to give an unstable hydroxylamine which was oxidised without isolation using iron(III) chloride to give methyl 3-nitrosothiophene-2-carboxylate. Condensation of this with methyl 3-aminothiophene-2-carboxylate furnished the azodiester. This was more conveniently obtained by manganese dioxide oxidation of the aminoester. Hydrolysis of the azodiester to give the diacid followed by decarboxylation gave 3,3′-azothiophene which could be oxidised to 3,3′-azoxythiophene with hydrogen peroxide. The azodiester was oxidised to the corresponding azoxydiester with urea-hydrogen peroxide/trifluoroacetic anhydride and reduced to the related hydrazothiophenediester with diimide.

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confidence: 99%

3,3′-Azothiophene

Glover

Huddleston

Wood

2013

Journal of Chemical Research

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“…Desilylation of compound 21 with tetra- n -butylammonium fluoride gave quinone 16 . Oxidation of dihydroquinone to benzoquinone under the NBS reaction conditions has been reported [22], however, oxidation under tetra- n -butylammonium fluoride reaction conditions is unexpected.…”

Section: Resultsmentioning

confidence: 99%

Redox potentials, laccase oxidation, and antilarval activities of substituted phenols

Prasain

Nguyen

Gorman

et al. 2012

Bioorganic & Medicinal Chemistry

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Laccases are copper-containing oxidases that are involved in sclerotization of the cuticle of mosquitoes and other insects. Oxidation of exogenous compounds by insect laccases may have the potential to produce reactive species toxic to insects. We investigated two classes of substituted phenolic compounds, halogenated di- and trihydroxybenzenes and substituted di-tert-butylphenols, on redox potential, oxidation by laccase and effects on mosquito larval growth. An inverse correlation between the oxidation potentials and laccase activity of halogenated hydroxybenzenes was found. Substituted di-tert-butylphenols however were found to impact mosquito larval growth and survival. In particular, 2,4-di-tert-butyl-6-(3-methyl-2-butenyl)phenol (15) caused greater than 98% mortality of Anopheles gambiae larvae in a concentration of 180 nM, whereas 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylpropanal oxime (13) and 6,8-di-tert-butyl-2,2-dimethyl-3,4-dihydro-2H-chromene (33) caused 93% and 92% mortalities in concentrations of 3.4 and 3.7 μM, respectively. Larvae treated with di-tert-butylphenolic compounds died just before pupation.

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“…A review of the oxidation and dehydrogenation reactions with NBS and related N ‐haloimides by Filler19 reported the oxidation of 2‐propanol,20 cyclohexanol,20 PVA,21 bezoin,22 ethylene glycol,23 and butanol23 with NBS and that of benzyl alcohol24 with N ‐bromoacetamide (NBA) as oxidizing agents. From the comparison of the respective yields of the oxidation products obtained by NBS/NBA and that by NBS supported on a polymeric support, it was observed that 2‐propanol (60 and 66.25%) and benzyl alcohol (75 and 70%) were comparable, whereas in the cases of cyclohexanol (61 and 50%) and benzoin (95 and 35%), the yields were lower.…”

Section: Resultsmentioning

confidence: 99%

Polyethylene‐supported N‐bromosuccinimide polymeric reagent for use in some oxidation reactions

Dhiman

Mahajan

Kaur

2011

J of Applied Polymer Sci

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We report a three‐step preparation of a polymer‐supported oxidizing reagent, polyethylene‐g‐N‐bromosuccinimide (PE‐g‐NBS), through the graft copolymerization of maleic anhydride (MAn) onto polyethylene (PE) by a photochemical method with 1% benzophenone as a photosensitizer. The postgrafting treatment of polyethylene‐g‐maleic anhydride (PE‐g‐MAn) with urea on fusion gives polyethylene‐g‐succinimide (PE‐g‐succinimide), which, on further treatment with an aqueous solution of sodium hydroxide and bromine, gives the required reagent, PE‐g‐NBS. The maximum percentage grafting (25%) was obtained with 3.57 mol of MAn and 0.5 mL of 1% benzophenone in 120 min. Fourier transform infrared spectroscopy and thermogravimetric analysis methods were used to characterize the graft copolymer PE‐g‐MAn, PE‐g‐succinimide, and the polymeric support, that is, PE‐g‐NBS. The grafted PE and the polymeric support were found to be thermally stable. The polymer‐supported N‐bromosuccinimide was used successfully for the efficient oxidation of a series of alcohols, including 2‐propanol, n‐butanol, ethylene glycol, cyclohexanol, poly(vinyl alcohol), benzoin, benzyl alcohol, and chloromycetin, to their corresponding aldehydes and ketones. The selectivity of PE‐g‐NBS toward the oxidation of secondary alcoholic groups without the disturbance of the primary alcoholic groups was reflected during the oxidation of chloromycetin. The oxidized products were characterized by Fourier transform infrared and 1H‐NMR spectral methods. The reagent was reused for the oxidation of fresh alcohols, and it was found to oxidize them successfully, although with a little lower product yield. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011

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Some Reactions with N-Bromosuccinimide

Cited by 33 publications

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3,3′-Azothiophene

3,3′-Azothiophene

Redox potentials, laccase oxidation, and antilarval activities of substituted phenols

Polyethylene‐supported N‐bromosuccinimide polymeric reagent for use in some oxidation reactions

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