Phase Transfer Catalysis

Mąkosza, Mieczysław; Fedoryński, M.

doi:10.1002/0471227617.eoc170.pub2

Cited by 7 publications

(8 citation statements)

References 100 publications

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“…In this technique, the monomer (acrylates) was dissolved in the organic solvent and initiator (PDS) is dissolved in water, these mixtures are immiscible in nature and then by adding PTC, polymerization reaction occur through the transport of one reactant into the other phase. The advantages of PTC are well documented in the literature [12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Comparative investigation on radical polymerization of methyl and ethyl methacrylate under multi-site phase-transfer catalytic conditions

Murugesan

Marimuthu

2018

Appl Petrochem Res

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Methyl and ethyl methacrylate was polymerized in heterogeneous system with the help of newly synthesized multi-site phase-transfer catalyst and using water-soluble initiator at 60 ± 1 °C under unstirred inert atmospheric condition. Polymer yield was increased with increasing molar concentrations of monomer, initiator, catalyst and temperature. Polymerization follows first-order kinetics with respect to monomer and half-order with respect to catalyst and initiator, respectively. PTC has myriads of applications in the synthesis of various organic and polymeric materials because of its fast reaction and high yield in short period of time. Without addition of PTC, polymerization did not occur; this indicates that catalyst plays the pivotal role on initiation of polymerization. It extracts the reactive radical anion from aqueous phase and transfers to the organic phase where acrylates were polymerized. Polymerization reactivity of methyl and ethyl methacrylate under PTC conditions was studied by various parameters. The activation energy (Ea) and other thermodynamic parameters were calculated. The Ea value supports the reactivity of acrylates. The results obtained from this investigation were used for inferring the radical mechanism of phase-transfer-catalyzed polymerization. The obtained polymers were analyzed by spectral and thermal analyses.

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Section: Introductionmentioning

confidence: 99%

Comparative investigation on radical polymerization of methyl and ethyl methacrylate under multi-site phase-transfer catalytic conditions

Murugesan

Marimuthu

2018

Appl Petrochem Res

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“…In the discussed work, the authors postulated two reaction mechanisms (Scheme 11), initiated by deprotonation according to the Mąkosza 30 interphase mechanism. In both versions, the key stage is the formation of an ionic pair between the catalyst and the substrate.…”

Section: Scheme 11 Enantioselective Cyclization Into Indole-type Prodmentioning

confidence: 99%

Assisted by Hydrogen-Bond Donors: Cinchona Quaternary Salts as Privileged Chiral Catalysts for Phase-Transfer Reactions

Majdecki¹,

Niedbała²,

Tyszka-Gumkowska³

et al. 2021

Synthesis

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This review is devoted to the asymmetric phase-transfer reactions with the use of hybrid ammonium <i>Cinchona</i> catalysts supported by hydrogen-bond donor groups. Herein, we present a recent advancement of this type of catalysts in the field of biphasic reaction systems. The main emphasis was put on the advantages of additional functional groups present in the structure of the catalysts, such as: hydroxyl, amide, (thio)urea or squareamide.

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“…Regioselective alkylation of diol 12 was also possible. Reaction of 12 with various alkylating agents such as, tertbutyl bromoacetate, allyl bromide, and propargyl bromide, performed under classical PTC conditions, 20,21 afforded compounds 16b-18b in decent yields (Table 1). Small amounts of regioisomers at the C-1′, 16c-18c, and dialkylated derivatives, 16a-18a, easily separated by column chromatography were, however, also formed.…”

Section: Figure 3 Application Of Penta-o-benzylsucrose For the Preparation Of Macrocyclic Derivativesmentioning

confidence: 99%

Novel Approach to Selectively Functionalized Derivatives of Sucrose

Kowalski

Cmoch

Jarosz

2014

Synlett

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General Information NMR spectra were recorded in CDCl 3 (internal Me 4 Si) with a Varian AM-600 (600 MHz 1 H, 150MHz 13 C) spectrometer at room temperature. Chemical shifts () are reported in ppm relative to Me 4 Si (0.00)for 1 H and residual chloroform (77.00) for 13 C. All significant resonances (carbon skeleton) were assigned by COSY (1 H-1 H), HSQC (1 H-13 C), and HMBC (1 H-13 C) correlations. Reagents were purchased from Sigma-Aldrich, Alfa Aesar or ABCR, and used without further purification. Commercial: THF, CH 2 Cl 2 and MeOH were dried over freshly activated (for at least 24h at 250 C) 3A molecular sieves for at least three days. Hexanes (65-80 C fraction from petroleum) and EtOAc were purified by distillation. Other solvents (pyridine, DMF, glacial AcOH and ACN) were used without further purification. Thin-layer chromatography was carried out on silica gel 60 F254 (Merck). Column chromatography was performed on silica gel 60 (70-230 mesh, Merck). Flash chromatography was performed on Buchi glass columns packed with silica gel 60 (230-400 mesh, Merck), using Knauer Smartline system with a Buchi fraction collector. The organic solutions were dried over MgSO 4 .Specific rotation was measured with a Jasco DIP-360 digital polarimeter for solution in CH 2 Cl 2 (c ~1) at room temperature. 5' To a solution of 12 (2.06 g;2.00mmol) in pyridine (20 mL) triphenylphosphine (1.15 g; 4.40 mmol; 2.2 equiv.) and 4-nitrobenzoic acid (0.50 g; 3.00 mmol; 1.5 equiv.) were added followed by a solution of diethyl azadicarboxylate (1.55 mL; 10 mmol; 5 equiv.) in toluene (3.5 mL). The mixture was stirred at rt. for 1.5 h. Pyridine was removed under reduced pressure, the oily residue was dissolved in xylene (20mL), and concentrated to ca. 1/3 volume. Then it was diluted with toluene (10 mL) and cooled to 4 ºC. Precipitated solid was filtered off and washed with cold (T-20ºC) mixture of toluene/hexane 1:1 (20 mL). The solution was concentrated and the residue was purified by column chromatography (hexanes/ethyl acetate 100:1 6:1) to afford alcohol 13 as a pale yellow thick oil (1.91 g; 1.62 mmol; 81%).

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Phase Transfer Catalysis

Cited by 7 publications

References 100 publications

Comparative investigation on radical polymerization of methyl and ethyl methacrylate under multi-site phase-transfer catalytic conditions

Comparative investigation on radical polymerization of methyl and ethyl methacrylate under multi-site phase-transfer catalytic conditions

Assisted by Hydrogen-Bond Donors: Cinchona Quaternary Salts as Privileged Chiral Catalysts for Phase-Transfer Reactions

Novel Approach to Selectively Functionalized Derivatives of Sucrose

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