Electrosynthesis in systems of two immiscible liquids and a phase transfer catalyst. V. The anodic chlorination of naphthalene

Ellis, S. R.; Pletcher, Derek; Brooks, W. N.; Healy, K. P.

doi:10.1007/bf00615823

Cited by 20 publications

(4 citation statements)

References 11 publications

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“…The growth and use of phase transfer catalyst (PTC) in the field of chemistry such as organic chemistry [1], inorganic chemistry [2], analytical applications [3], electrochemistry [4][5][6][7][8], photochemistry [9,10] and in polymer chemistry [11][12][13][14][15] has become increasingly popular within industrial and academic arenas, because it is a potent and versatile technology which offers (1) less dependence on organic solvents, (2) excellent scalability and inherent compatibility with moisture, (3) enhancement of reactivity, which permits shortened reaction times and increased yields, (4) ability to substitute inconvenient reagents [like lithium diisopropylamide (LDA)] and (5) to control enantioselective variants and eco-friendliness. The efficient source of PTC technology in synthesis of polymers offers important technical rewards compared to other conventional polymerization methods [16].…”

Section: Introductionmentioning

confidence: 99%

Phase transfer catalyst aided radical polymerization of n-butyl acrylate in two-phase system: a kinetic study

Murugesan

Umapathy

2016

Int J Ind Chem

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The kinetics of radical polymerization of butyl acrylate initiated by potassium peroxydisulphate and cetyltrimethylammonium bromide as phase transfer catalyst (PTC) was carried out under inert and unstirred conditions at constant temperature of 60 ± 2°C in ethyl acetate-water biphase media. The polymerization reactions were relatively fast in the two-phase systems with phase transfer agent whereas extremely sluggish in the system without PTC. Use of PTC accelerates the reaction effectively if the reactants located in two phase. The effects of rate of polymerization (R p ) on various experimental conditions such as different concentrations of monomer, initiator, phase transfer catalyst, temperature, and different ionic strength of the medium were explored. The order with respect to monomer, initiator and phase transfer catalyst was found to be unity. The R p is independent of ionic strength and pH of the medium. However, an increase in the polarity of solvent has slightly increased the R p value. Based on the results obtained, a plausible mechanism has been proposed for the polymerization reaction. The obtained polymer was confirmed by FT-IR analysis.

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Section: Introductionmentioning

confidence: 99%

Phase transfer catalyst aided radical polymerization of n-butyl acrylate in two-phase system: a kinetic study

Murugesan

Umapathy

2016

Int J Ind Chem

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“…356 In contrast to the electrochemical fluorination strategies, the anodic oxidation protocols involving chlorides, bromides and iodides typically proceed via generation of the corresponding electrophilic molecular counterpart (X 2 ) due to the relatively low oxidation potentials of these halogen ions. [357][358][359][360][361][362][363][364][365][366][367] Due to the limited solubility of alkali metal halide salts in organic solvents, a biphasic system consisting of an aqueous phase and a halogenated organic solvent is commonly employed to affect chlorination of aromatics 368,369 and heterocycles 370 as well as bromination of toluene derivatives. 371 The electrodes are placed in the upper layer of the aqueous phase, thus enabling selective oxidation of the halide.…”

Section: Anodic Halogenationmentioning

confidence: 99%

Electrochemical strategies for C–H functionalization and C–N bond formation

2018

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Conventional methods for carrying out carbon-hydrogen functionalization and carbon-nitrogen bond formation are typically conducted at elevated temperatures, and rely on expensive catalysts as well as the use of stoichiometric, and perhaps toxic, oxidants. In this regard, electrochemical synthesis has recently been recognized as a sustainable and scalable strategy for the construction of challenging carbon-carbon and carbon-heteroatom bonds. Here, electrosynthesis has proven to be an environmentally benign, highly effective and versatile platform for achieving a wide range of nonclassical bond disconnections via generation of radical intermediates under mild reaction conditions. This review provides an overview on the use of anodic electrochemical methods for expediting the development of carbon-hydrogen functionalization and carbon-nitrogen bond formation strategies. Emphasis is placed on methodology development and mechanistic insight and aims to provide inspiration for future synthetic applications in the field of electrosynthesis.

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“…Addition of ZnCl 2 to the electrolysis increases the yield of l-chloronaphthalene up to 92% (49% current efficiency), apparently due to the higher oxidizing selectivity of [Bu4N]2 ZnCl4 [306][307][308][309][310]. Addition of ZnCl 2 to the electrolysis increases the yield of l-chloronaphthalene up to 92% (49% current efficiency), apparently due to the higher oxidizing selectivity of [Bu4N]2 ZnCl4 [306][307][308][309][310].…”

Section: N Ptc Electrochemical Oxidationsmentioning

confidence: 99%