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Search for "alkylphenols" in Full Text gives 3 result(s) in Beilstein Journal of Organic Chemistry.
Cross-linked cyclodextrin-based material for treatment of metals and organic substances present in industrial discharge waters
- Élise Euvrard,
- Nadia Morin-Crini,
- Coline Druart,
- Justine Bugnet,
- Bernard Martel,
- Cesare Cosentino,
- Virginie Moutarlier and
- Grégorio Crini
Beilstein J. Org. Chem. 2016, 12, 1826–1838, doi:10.3762/bjoc.12.172
- hydrocarbons (PAH) and three alkylphenols (AP), the material exhibited high adsorption capacities: >99% of Co2+, Ni2+ and Zn2+ were removed, between 65 and 82% of the PAHs, as well as 69 to 90% of the APs. Due to the structure of the polymer and its specific characteristics, such as the presence of carboxylic
- calcium at high concentrations, which competed with other pollutants for the adsorption sites of the adsorbent. Keywords: alkylphenols; adsorption; cyclodextrin; metals; polycyclic aromatic hydrocarbons; Introduction Although considerable efforts have been made by the industrial sector over the last 30
- polycyclic aromatic hydrocarbons (PAHs) and alkylphenols (APs) at concentrations varying from hundreds of nanograms per liter to some micrograms per liter [1]. However, it is extremely difficult to remove pollutants present at low concentrations (a few hundreds of micrograms per liter for some organic
Graphical Abstract
Figure 1: Chemical structure of the non-activated polyBTCA-CD.
Figure 2: Determination of the PZC for the non-activated and activated polyBTCA-CD polymers (pHi: initial pH ...
Figure 3: XRD pattern of the two polymers: non-activated and activated polyBTCA-CD.
Figure 4: CPMAS and MAS spectra of polyBTCA-CD.
Figure 5: Adsorption capacity (%) of (a) the non-activated and (b) the activated (NaHCO3 treatment) polyBTCA-...
Figure 6: Adsorption kinetics for two solutions containing five metals at two concentrations (solution at 10 ...
Figure 7: Removal efficiency (%) after treatment with activated polyBTCA-CD (concentration = 2 g·L−1) for (a)...
Figure 8: Removal efficiency (%) of inorganic elements after treatment of five DWs by polyBTCA-CD (concentrat...
Cross-dehydrogenative coupling for the intermolecular C–O bond formation
- Igor B. Krylov,
- Vera A. Vil’ and
- Alexander O. Terent’ev
Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13
Graphical Abstract
Scheme 1: Cross-dehydrogenative coupling.
Scheme 2: Cross-dehydrogenative C–O coupling.
Scheme 3: Regioselective ortho-acetoxylation of meta-substituted arylpyridines and N-arylamides.
Scheme 4: ortho-Acyloxylation and alkoxylation of arenes directed by pyrimidine, benzoxazole, benzimidazole a...
Scheme 5: Cu(OAc)2/AgOTf/O2 oxidative system in the ortho-alkoxylation of arenes.
Scheme 6: Pd(OAc)2/persulfate oxidative system in the ortho-alkoxylation and acetoxylation of arenes with nit...
Scheme 7: ortho-Acetoxylation and methoxylation of O-methyl aryl oximes, N-phenylpyrrolidin-2-one, and (3-ben...
Scheme 8: Ruthenium-catalyzed ortho-acyloxylation of acetanilides.
Scheme 9: Acetoxylation and alkoxylation of arenes with amide directing group using Pd(OAc)2/PhI(OAc)2 oxidat...
Scheme 10: Alkoxylation of azoarenes, 2-aryloxypyridines, picolinamides, and N-(1-methyl-1-(pyridin-2-yl)ethyl...
Scheme 11: Acetoxylation of compounds containing picolinamide and quinoline-8-amine moieties using the Pd(OAc)2...
Scheme 12: (CuOH)2CO3 catalyzed oxidative ortho-etherification using air as oxidant.
Scheme 13: Copper-catalyzed aerobic alkoxylation and aryloxylation of arenes containing pyridine-N-oxide moiet...
Scheme 14: Cobalt-catalyzed aerobic alkoxylation of arenes and alkenes containing pyridine N-oxide moiety.
Scheme 15: Non-symmetric double-fold C–H ortho-acyloxylation.
Scheme 16: N-nitroso directed ortho-alkoxylation of arenes.
Scheme 17: Selective alkoxylation and acetoxylation of alkyl groups.
Scheme 18: Acetoxylation of 2-alkylpyridines and related compounds.
Scheme 19: Acyloxylation and alkoxylation of alkyl fragments of substrates containing amide or sulfoximine dir...
Scheme 20: Palladium-catalyzed double sp3 C–H alkoxylation of N-(quinolin-8-yl)amides for the synthesis of sym...
Scheme 21: Copper-catalyzed acyloxylation of methyl groups of N-(quinolin-8-yl)amides.
Scheme 22: One-pot acylation and sp3 C–H acetoxylation of oximes.
Scheme 23: Possible mechanism of oxidative esterification catalyzed by N-heterocyclic nucleophilic carbene.
Scheme 24: Oxidative esterification employing stoichiometric amounts of aldehydes and alcohols.
Scheme 25: Selective oxidative coupling of aldehydes with alcohols in the presence of amines.
Scheme 26: Iodine mediated oxidative esterification.
Scheme 27: Oxidative C–O coupling of benzyl alcohols with methylarenes under the action of Bu4NI/t-BuOOH syste...
Scheme 28: Oxidative coupling of methyl- and ethylarenes with aromatic aldehydes under the action of Bu4NI/t-B...
Scheme 29: Cross-dehydrogenative C–O coupling of aldehydes with t-BuOOH in the presence of Bu4NI.
Scheme 30: Bu4NI-catalyzed α-acyloxylation reaction of ethers and ketones with aldehydes and t-BuOOH.
Scheme 31: Oxidative coupling of aldehydes with N-hydroxyimides and hexafluoroisopropanol.
Scheme 32: Oxidative coupling of alcohols with N-hydroxyimides.
Scheme 33: Oxidative coupling of aldehydes and primary alcohols with N-hydroxyimides using (diacetoxyiodo)benz...
Scheme 34: Proposed mechanism of the oxidative coupling of aldehydes and N-hydroxysuccinimide under action of ...
Scheme 35: Oxidative coupling of aldehydes with pivalic acid (172).
Scheme 36: Oxidative C–O coupling of aldehydes with alkylarenes using the Cu(OAc)2/t-BuOOH system.
Scheme 37: Copper-catalyzed acyloxylation of C(sp3)-H bond adjacent to oxygen in ethers using benzyl alcohols.
Scheme 38: Oxidative C–O coupling of aromatic aldehydes with cycloalkanes.
Scheme 39: Ruthenium catalyzed cross-dehydrogenative coupling of primary and secondary alcohols.
Scheme 40: Cross-dehydrogenative C–O coupling reactions of β-dicarbonyl compounds with sulfonic acids, acetic ...
Scheme 41: Acyloxylation of ketones, aldehydes and β-dicarbonyl compounds using carboxylic acids and Bu4NI/t-B...
Scheme 42: Acyloxylation of ketones using Bu4NI/t-BuOOH system.
Scheme 43: Cross-dehydrogenative C–O coupling of β-dicarbonyl compounds and their heteroanalogues with N-hydro...
Scheme 44: Cross-dehydrogenative C–O coupling of β-dicarbonyl compounds and their heteroanalogues with t-BuOOH....
Scheme 45: Oxidative C–O coupling of 2,6-dialkylphenyl-β-keto esters and thioesters with tert-butyl hydroxycar...
Scheme 46: α’-Acyloxylation of α,β-unsaturated ketones using KMnO4.
Scheme 47: Possible mechanisms of the acetoxylation at the allylic position of alkenes by Pd(OAc)2.
Scheme 48: Products of the oxidation of terminal alkenes by Pd(II)/AcOH/oxidant system.
Scheme 49: Acyloxylation of terminal alkenes with carboxylic acids.
Scheme 50: Synthesis of linear E-allyl esters by cross-dehydrogenative coupling of terminal alkenes wih carbox...
Scheme 51: Pd(OAc)2-catalyzed acetoxylation of Z-vinyl(triethylsilanes).
Scheme 52: α’-Acetoxylation of α-acetoxyalkenes with copper(II) chloride in acetic acid.
Scheme 53: Oxidative acyloxylation at the allylic position of alkenes and at the benzylic position of alkylare...
Scheme 54: Copper-catalyzed alkoxylation of methylheterocyclic compounds using di-tert-butylperoxide as oxidan...
Scheme 55: Oxidative C–O coupling of methylarenes with β-dicarbonyl compounds or phenols.
Scheme 56: Copper-catalyzed esterification of methylbenzenes with cyclic ethers and cycloalkanes.
Scheme 57: Oxidative C–O coupling of carboxylic acids with toluene catalyzed by Pd(OAc)2.
Scheme 58: Oxidative acyloxylation at the allylic position of alkenes with carboxylic acids using the Bu4NI/t-...
Scheme 59: Cross-dehydrogenative C–O coupling of carboxylic acids with alkylarenes using the Bu4NI/t-BuOOH sys...
Scheme 60: Oxidative C–O cross-coupling of methylarenes with ethyl or isopropylarenes.
Scheme 61: Phosphorylation of benzyl C–H bonds using the Bu4NI/t-BuOOH oxidative system.
Scheme 62: Selective C–H acetoxylation of 2,3-disubstituted indoles.
Scheme 63: Acetoxylation of benzylic position of alkylarenes using DDQ as oxidant.
Scheme 64: C–H acyloxylation of diarylmethanes, 3-phenyl-2-propen-1-yl acetate and dimethoxyarene using DDQ.
Scheme 65: Cross-dehydrogenative C–O coupling of 1,3-diarylpropylenes and 1,3-diarylpropynes with alcohols.
Scheme 66: One-pot azidation and C–H acyloxylation of 3-chloro-1-arylpropynes.
Scheme 67: Cross-dehydrogenative C–O coupling of 1,3-diarylpropylenes, (E)-1-phenyl-2-isopropylethylene and is...
Scheme 68: Cross-dehydrogenative C–O coupling of alkylarenes and related compounds with N-hydroxyphthalimide.
Scheme 69: Acetoxylation at the benzylic position of alkylarenes mediated by N-hydroxyphthalimide.
Scheme 70: C–O coupling of methylarenes with aromatic carboxylic acids employing the NaBrO3/NaHSO3 system.
Scheme 71: tert-Butyl peroxidation of allyl, propargyl and benzyl ethers catalyzed by Fe(acac)3.
Scheme 72: Cross-dehydrogenative C–O coupling of ethers with carboxylic acids mediated by Bu4NI/t-BuOOH system....
Scheme 73: Oxidative acyloxylation of dimethylamides and dioxane with 2-aryl-2-oxoacetic acids accompanied by ...
Scheme 74: tert-Butyl peroxidation of N-benzylamides and N-allylbenzamide using the Bu4NI/t-BuOOH system.
Scheme 75: Cross-dehydrogenative C–O coupling of aromatic carboxylic acids with ethers using Fe(acac)3 as cata...
Scheme 76: Cross-dehydrogenative C–O coupling of cyclic ethers with 2-hydroxybenzaldehydes using iron carbonyl...
Scheme 77: Cross-dehydrogenative C–O coupling of ethers with β-dicarbonyl compounds and phenols using copper c...
Scheme 78: Cross-dehydrogenative C–O coupling of 2-hydroxybenzaldehyde with dioxane catalyzed by Cu2(BPDC)2(BP...
Scheme 79: Ruthenium chloride-catalyzed acyloxylation of β-lactams.
Scheme 80: Ruthenium-catalyzed tert-butyl peroxydation amides and acetoxylation of β-lactams.
Scheme 81: PhI(OAc)2-mediated α,β-diacetoxylation of tertiary amines.
Scheme 82: Electrochemical oxidative methoxylation of tertiary amines.
Scheme 83: Cross-dehydrogenative C–O coupling of ketene dithioacetals with carboxylic acids in the presence of...
Scheme 84: Cross-dehydrogenative C–O coupling of enamides with carboxylic acids using iodosobenzene as oxidant....
Scheme 85: Oxidative alkoxylation, acetoxylation, and tosyloxylation of acylanilides using PhI(O(O)CCF3)2 in t...
Scheme 86: Proposed mechanism of the oxidative C–O coupling of actetanilide with O-nucleophiles in the presenc...
Scheme 87: Three-component coupling of aldehydes, anilines and alcohols involving oxidative intermolecular C–O...
Scheme 88: Oxidative coupling of phenols with alcohols.
Scheme 89: 2-Acyloxylation of quinoline N-oxides with arylaldehydes in the presence of the CuOTf/t-BuOOH syste...
Scheme 90: Cross-dehydrogenative C–O coupling of azoles with primary alcohols.
Scheme 91: Oxidation of dipyrroles to dipyrrins and subsequent oxidative alkoxylation in the presence of Na3Co...
Scheme 92: Oxidative dehydrogenative carboxylation of alkanes and cycloalkanes to allylic esters.
Scheme 93: Pd-catalyzed acetoxylation of benzene.
End-group-functionalized poly(N,N-diethylacrylamide) via free-radical chain transfer polymerization: Influence of sulfur oxidation and cyclodextrin on self-organization and cloud points in water
- Sebastian Reinelt,
- Daniel Steinke and
- Helmut Ritter
Beilstein J. Org. Chem. 2014, 10, 680–691, doi:10.3762/bjoc.10.61
- synthesis of thermo-, oxidation- and cyclodextrin- (CD) responsive end-group-functionalized polymers, based on N,N-diethylacrylamide (DEAAm). In a classical free-radical chain transfer polymerization, using thiol-functionalized 4-alkylphenols, namely 3-(4-(1,1-dimethylethan-1-yl)phenoxy)propane-1-thiol and
- -diethylacrylamide) has not been investigated. Results and Discussion Synthesis of thiol functionalized 4-alkylphenols. As depicted in Scheme 1, the synthesis of the thiol-functionalized phenol derivatives was accomplished in a three step synthesis. Etherification of the phenolic hydroxy groups of 1a and 1b with
- Supporting Information File 1, Figures S1 to S4 for the 1H and 13C NMR data). Synthesis of the end-group functionalized polymers. The thiol functionalized 4-alkylphenols (6a and 6b) were used as chain transfer agents (CTA) for the free-radical polymerization of N,N-diethylacrylamide (DEAAm) (7) (see Scheme 2
Graphical Abstract
Scheme 1: Synthetic route for the synthesis of thiol functionalized 4-alkylphenols.
Scheme 2: Synthetic route for the chain transfer polymerization of N,N-diethylacrylamide (7) with CTA 6a and ...
Figure 1: Section of the MALDI –TOF spectrum of polymer 8b, indicating the high degree of end-group functiona...
Figure 2: 1H NMR spectrum of polymer 9b in CDCl3 (300 MHz, rt).
Figure 3: Top left: Section of the FTIR-spectrum of polymer 8b (black line) in comparison to 8bOx (red line);...
Figure 4: Dependency of the cloud point values on the degree of polymerization (calculated by end-group analy...
Figure 5: Shifts of the cloud points after the oxidation of the polymers (8a–d, 9a–d) to its corresponding su...
Figure 6: Turbidimetry measurements of polymer 8b (straight black line – heating curve; dotted black line – c...
Figure 7: 2D NMR NOESY spectrum of polymer 8b with two equivalents RAMEB-CD in D2O (600 MHz, rt).
Figure 8: Left: Schematic illustration of the micellar-like structures and reversibility by addition of RAMEB...
Figure 9: Schematic illustration of the micellar-like structures, its deformation upon addition of one equiva...
