Stabilization of nanosized titanium dioxide by cyclodextrin polymers and its photocatalytic effect on the degradation of wastewater pollutants

• Tamás Zoltán Agócs,
• István Puskás,
• Erzsébet Varga,
• Mónika Molnár and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2016, 12, 2873–2882, doi:10.3762/bjoc.12.286

• oligosaccharides consisting of 6–8 glucose units (α-, β- and γ-CD) primarily used in the pharmaceutical, cosmetic and household chemical industry [8]. They form non-covalent inclusion complexes with a great number of the organic contaminants in soil (petroleum hydrocarbons, polycyclic aromatic hydrocarbons, etc

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

A flow reactor setup for photochemistry of biphasic gas/liquid reactions

• Josef Schachtner,
• Patrick Bayer and
• Axel Jacobi von Wangelin

Beilstein J. Org. Chem. 2016, 12, 1798–1811, doi:10.3762/bjoc.12.170

• described set-up operates residence times of up to 30 min which cover the typical rates of many organic reactions. The tubular microreactor was successfully applied to the photooxygenation of hydrocarbons (Schenck ene reaction). Major emphasis was laid on the realization of a constant and highly

Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates

• Jarosław Lewkowski,
• Maria Rodriguez Moya,
• Anna Wrona-Piotrowicz,
• Janusz Zakrzewski,
• Renata Kontek and
• Gabriela Gajek

Beilstein J. Org. Chem. 2016, 12, 1229–1235, doi:10.3762/bjoc.12.117

• [2] or anticancer properties [3]. Various C-aryl substituted derivatives of phosphonoglycine have been synthesized including those of benzene and several polycyclic aromatic hydrocarbons [4], five- [5] and six-membered [6] heteroaromatic compounds and even ferrocene [7]. In contrast, pyrene-based

Stimuli-responsive HBPS-g-PDMAEMA and its application as nanocarrier in loading hydrophobic molecules

• Yongsheng Chen,
• Li Wang,
• Haojie Yu,
• Zain-Ul-Abdin,
• Ruoli Sun,
• Guanghui Jing,
• Rongbai Tong and
• Zheng Deng

Beilstein J. Org. Chem. 2016, 12, 939–949, doi:10.3762/bjoc.12.92

• environmentally located polarity of encapsulated pyrene. Figure 7C,D showed that the intensity of I3 (normalized at I1) was increased to 0.68, as concentration of HBPE-g-PDMAEMA was increased to 2.0 mg/mL. Although this value is much lower than pure aliphatic hydrocarbons (1.65–1.8) [24], the improvement compared

Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N–O bond-forming cyclization of 2-azidobenzoic acids

• Daria Yu. Dzhons and
• Andrei V. Budruev

Beilstein J. Org. Chem. 2016, 12, 874–881, doi:10.3762/bjoc.12.86

• in the photolysis reactions of aryl azides without participating ortho-substituents in hydrocarbons as the solvents [39]. In the present research it is demonstrated that using ethanol as the solvent for the photolysis reaction leads to benzisoxazole 2a with an increased yield of 35% and the yield can

Biocatalysis for the application of CO₂ as a chemical feedstock

• Apostolos Alissandratos and
• Christopher J. Easton

Beilstein J. Org. Chem. 2015, 11, 2370–2387, doi:10.3762/bjoc.11.259

• of CO2 to CO through in vitro application of CODH has been of interest as the enzymatic product may be further converted into hydrocarbons through the Fischer–Tropsch process [146]. In work carried out by Armstrong, Ragsdale and coworkers [147][148], metal oxide nanoparticles were functionalised with

• CODH and photosensitised with a Ru dye to catalyse the reduction of CO2 using visible light. Further to this, the reported ability of a V-dependent nitrogenase to slowly reduce CO to various small-chain hydrocarbons holds much promise for the development of enzymatic processes to further transform CO

Recent advances in copper-catalyzed C–H bond amidation

• Jie-Ping Wan and
• Yanfeng Jing

Beilstein J. Org. Chem. 2015, 11, 2209–2222, doi:10.3762/bjoc.11.240

• to give the corresponding quinoline derivatives 56 by simply treating 54 with PCl3 (Scheme 15). As another kind of conventional unsaturated hydrocarbons, the alkenes had been found to show similar reactivity with arenes in many cross coupling reactions. However, in the C–H amidation chemistry, the

Supramolecular chemistry: from aromatic foldamers to solution-phase supramolecular organic frameworks

• Zhan-Ting Li

Beilstein J. Org. Chem. 2015, 11, 2057–2071, doi:10.3762/bjoc.11.222

• molecules to evaluate their binding to these triazole foldamers. He finally found that these foldamers were good halogen bonding receptors for tritopic and ditopic guests, including 30 in dichloromethane or its mixture with hydrocarbons. Yanhua further utilized the C–H····F hydrogen bonding to induce the

Cross-metathesis of polynorbornene with polyoctenamer: a kinetic study

• Yulia I. Denisova,
• Maria L. Gringolts,
• Alexander S. Peregudov,
• Liya B. Krentsel,
• Ekaterina A. Litmanovich,
• Arkadiy D. Litmanovich,
• Eugene Sh. Finkelshtein and
• Yaroslav V. Kudryavtsev

Beilstein J. Org. Chem. 2015, 11, 1796–1808, doi:10.3762/bjoc.11.195

• and PCOE are commonly synthesized by ring-opening metathesis polymerization (ROMP). PNB is a well-known commercial product available under the trademark Norsorex® [8][16], which is mainly used as a solidifier of oil and solvent for the complete absorption of oil or other hydrocarbons. PCOE, known as

Active site diversification of P450cam with indole generates catalysts for benzylic oxidation reactions

• Paul P. Kelly,
• Anja Eichler,
• Susanne Herter,
• David C. Kranz,
• Nicholas J. Turner and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2015, 11, 1713–1720, doi:10.3762/bjoc.11.186

• hydroxylations. Keywords: active site mutagenesis; biotransformation; C–H activation; cytochrome P450cam monooxygenase; hydroxylation; Introduction Selective C–H activation and oxyfunctionalisation of hydrocarbons offers a route to chiral alcohols and other industrially important synthetic building blocks from

• –alkyl compounds [3], olefins [4], polycyclic aromatic hydrocarbons [5], terpenes [6][7][8] and alkanes as small as ethane [9]. Over the years a number of active site mutants of P450cam have been generated by rational re-design, but the active site has not been explored in a comprehensive and systematic

The chemical behavior of terminally tert-butylated polyolefins

• Dagmar Klein,
• Henning Hopf,
• Peter G. Jones,
• Ina Dix and
• Ralf Hänel

Beilstein J. Org. Chem. 2015, 11, 1246–1258, doi:10.3762/bjoc.11.139

• particular the distortions associated with the bulky tert-butyl groups. For all these hydrocarbons, di-tert-butylketone (1) served as the starting material, which was chain-elongated by preparative sequences involving standard Wittig, Wittig–Horner and McMurry coupling reactions. Nearly all of the polyenes 2

• of the hydrocarbons 2. Results and Discussion Catalytic hydrogenation We started our studies on the reactive behavior of polyolefins 2 with one of the formally simplest alkene reactions: catalytic hydrogenation. When diene 3 was hydrogenated under relatively mild conditions (Pd/C, EtOH, room temp

• is known about their basic photochemical reactions, such as photoisomerizations and/or photoadditions. For the unsubstituted hydrocarbons, this is not surprising in view of their general instability and the difficulty of obtaining pure diastereomers. With our stabilized oligoenes in hand, we started

Properties of PTFE tape as a semipermeable membrane in fluorous reactions

• Brendon A. Parsons,
• Olivia Lin Smith,
• Myeong Chae and
• Veljko Dragojlovic

Beilstein J. Org. Chem. 2015, 11, 980–993, doi:10.3762/bjoc.11.110

• tape. Second, the compound of interest must be fairly soluble in the solvent which has filled the void space in the PTFE tape. Dimethyl phthalate is insoluble in solvents which are non-polar (aliphatic hydrocarbons such as hexanes) or highly-polar (water), but dissolves well in medium-polarity solvents

Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles

• Grzegorz Mlostoń,
• Paulina Grzelak,
• Maciej Mikina,
• Anthony Linden and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2015, 11, 576–582, doi:10.3762/bjoc.11.63

• the present study were used for oxidation reactions aimed at the preparation of the corresponding sulfoxides and sulfones. As demonstrated in a recent publication [20], polycyclic sulfones are attractive substrates for the synthesis of polycyclic hydrocarbons via thermal SO2 extrusion. In our

The preparation of new functionalized [2.2]paracyclophane derivatives with N-containing functional groups

• Henning Hopf,
• Swaminathan Vijay Narayanan and
• Peter G. Jones

Beilstein J. Org. Chem. 2015, 11, 437–445, doi:10.3762/bjoc.11.50

• co-workers [6]. The corresponding perchloro and perbromo derivatives are apparently unknown. Other notable oligofluoro hydrocarbons are the octafluoro derivative 3 with eight fluorine substituents in Sb positions [7][8][9][10], and its isomer 4 with the eight fluorine substituents attached to the two

Electrochemical oxidation of cholesterol

• Jacek W. Morzycki and
• Andrzej Sobkowiak

Beilstein J. Org. Chem. 2015, 11, 392–402, doi:10.3762/bjoc.11.45

• numeral, but the acetylated derivative is amended by the letter “a”, e.g., cholesterol (1) and cholesteryl acetate (1a). Indirect electrochemical oxidation of cholesterol The selective oxidation of saturated hydrocarbons by dioxygen and hydrogen peroxide remains a challenging problem in chemistry and

• . Many investigations on oxygenation reactions have been carried out by using a simple, readily available reagent system mimicking monooxygenase enzymes. An interesting system for the oxidation of aliphatic hydrocarbons, consisting of oxygen, powdered zinc, pyridine, acetic acid, and a catalytic amount

Attempts to prepare an all-carbon indigoid system

• Şeref Yildizhan,
• Henning Hopf and
• Peter G. Jones

Beilstein J. Org. Chem. 2015, 11, 363–372, doi:10.3762/bjoc.11.42

• ], the recent preparative accomplishments of the Sherburn group have changed the situation fundamentally [5][6]. These cross-conjugated hydrocarbons are now known up to [13]dendralene, and many of these potentially very valuable compounds are available in gram quantities, allowing, often for the first

• always in the form of mixtures also containing other isomers. As far as we are aware, the above route is the only one that provides isomerically pure 23, not surprising in view of its route of formation. These isomeric hydrocarbons are useful ligands for the preparation of bridged Ziegler–Natta catalysts

• tert-BuLi in THF and the presumably resulting bis-anion quenched with 1,2-dibromoethane, a complex product mixture consisting largely of polymeric material was formed. From this mixture, however, trace amounts of two hydrocarbons (total yield 5%) could be separated by thin layer chromatography. Further

Articulated rods – a novel class of molecular rods based on oligospiroketals (OSK)

• Pablo Wessig,
• Roswitha Merkel and
• Peter Müller

Beilstein J. Org. Chem. 2015, 11, 74–84, doi:10.3762/bjoc.11.11

• these types should therefore facilitate very interesting applications for ARs. As mentioned above, compound 32a can serve as a probe for this equilibrium owing to the pyrene moieties. As many polyaromatic hydrocarbons pyrene possess a marked tendency to form excimers in the excited state [23]. The broad

Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs

• Lisa F. Becker,
• Dennis H. Schwarz and
• Gerhard Wenz

Beilstein J. Org. Chem. 2014, 10, 2920–2927, doi:10.3762/bjoc.10.310

• affinity towards rocuronium [24][25]. Furthermore, hydrophilic γ-CD thioethers show high affinities to other guests such as polycyclic aromatic hydrocarbons [26], botulin [27][28], and fullerene C60 [29]. Hydrophilic β-CD thioethers also tightly complex volatile benzene derivatives leading to a significant

Thermal and oxidative stability of the Ocimum basilicum L. essential oil/β-cyclodextrin supramolecular system

• Daniel I. Hădărugă,
• Nicoleta G. Hădărugă,
• Corina I. Costescu,
• Ioan David and
• Alexandra T. Gruia

Beilstein J. Org. Chem. 2014, 10, 2809–2820, doi:10.3762/bjoc.10.298

• properties, and its antimicrobial [19] biological effects. Moreover, the anticancer potential of basil components has been studied [24]. These sensory and pharmaceutical properties of basil are primarily due to the presence of essential oil components, which consist of monoterpene hydrocarbons (e.g., β

• -pinene), oxygenated monoterpenes (eucalyptol, linalool, α-terpineol, borneol and its acetate), phenolic derivatives (eugenol, methylchavicol (estragole)), sesquiterpene hydrocarbons (β-cubebene, β-caryophyllene, germacrene, etc.), and oxygenated sesquiterpenes (cadinol, spathulenol) [9][16][20][25

• for sesquiterpenes (hydrocarbons), in comparison with the corresponding oxygenated sesquiterpenes exists. The above mentioned α-cadinol (18) and spathulenol (16) were identified in the encapsulated essential oil at reduced concentrations of 34.5% and 84.5%, respectively. This reduction in

Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphism

• Joscha Vollmeyer,
• Friederike Eberhagen,
• Sigurd Höger and
• Stefan-S. Jester

Beilstein J. Org. Chem. 2014, 10, 2774–2782, doi:10.3762/bjoc.10.294

• –HOPG and macrocycle–macrocycle interactions, the following key aspects must be considered: (i) how the extraannular alkyl side chains of the adsorbed macrocycles pack, and whether this can be compared to the packing of linear hydrocarbons on HOPG, (ii) how the specific attachment of the extraannular

Removal of volatile organic compounds using amphiphilic cyclodextrin-coated polypropylene

• Ludmilla Lumholdt,
• Sophie Fourmentin,
• Thorbjørn T. Nielsen and
• Kim L. Larsen

Beilstein J. Org. Chem. 2014, 10, 2743–2750, doi:10.3762/bjoc.10.290

• in order to improve the aquatic ecosystem [1]. Later in 2008, the EU elaborated on the Water Framework Directive defining several problematic compounds, including various pesticides, endocrine disruptors, and hydrocarbons such as benzene and benzene derivatives, as compounds requiring immediate and

• could provide a full removal of the tested compounds [3]. Biological treatment of wastewater shows a high efficiency towards the removal of hydrocarbons, however, some bacteria cannot tolerate the elevated concentrations of the chemicals, resulting in a low removal efficiency [4][5][6]. Consequently

Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

• Véronique Nardello-Rataj and
• Loïc Leclercq

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

• complexes. Therefore, the essential oils were protected by the β-CD encapsulation. As a consequence, the essential oils remain effective as antimicrobial agents for longer time periods and under a wide variety of environmental conditions. On the other hand, the biodegradation of hydrocarbons is influenced

• by their bioavailability [52]. Indeed, hydrocarbons are very poorly soluble in water. Therefore, their metabolization by microorganisms is very difficult. To overcome this drawback, surfactants are used to improve their aqueous solubility and their bioavailability in order to accelerate the

Microsolvation and sp²-stereoinversion of monomeric α-(2,6-di-tert-butylphenyl)vinyllithium as measured by NMR

• Rudolf Knorr,
• Monika Knittl and
• Eva C. Rossmann

Beilstein J. Org. Chem. 2014, 10, 2521–2530, doi:10.3762/bjoc.10.263

• immediately from 5 with n-Bu6Li in the absence of TMEDA in a less clean (pale violet) THF/hydrocarbons mixture (47:53% by volume). These coincidences established that even considerable amounts of residual n-Bu6Li and the emerging tetrameric Me6Li did not form mixed aggregates with 4 in THF. The further

• , [15]), whereas the notoriously variable [19] 1H NMR data evaded a simple interpretation. Importantly, separate NMR signals were observed for free and coordinated TMEDA (1 equiv) at and below −44 °C. In TMEDA/hydrocarbons (64:36) as the solvent, the quick Sn/Li interchange reaction of 5 with n-Bu6Li at

• , [15]). The high concentration of (CH3Li)4 did not change during the slow decay of 4&TMEDA at rt through proton transfer from the solvent TMEDA [20][21] that formed olefin 8a, Me2N–CH=CH2, and LiNMe2. In Et2O/hydrocarbons (54:46) without TMEDA, the Sn/Li interchange reaction of 5 and n-Bu6Li was very

Electrocarboxylation: towards sustainable and efficient synthesis of valuable carboxylic acids

• Roman Matthessen,
• Jan Fransaer,
• Koen Binnemans and
• Dirk E. De Vos

Beilstein J. Org. Chem. 2014, 10, 2484–2500, doi:10.3762/bjoc.10.260

• process provides a feasible route to methoxymethane-1,1,1’-tricarboxylate salts, which are excellent detergent builders. The reaction should be carried out in strictly anhydrous conditions, since water is a stronger acid than the weakly acidic hydrocarbons employed herein. Electrogenerated bromine is used

• −, ClO4−, HSO4−, Cl−, Br− [147]. General scheme of carboxylation of weak acidic hydrocarbons with electrogenerated bases. RH: weakly acidic hydrocarbon; BP: base precursor; EGB−: electrogenerated base; EGBH: conjugate acid of electrogenerated base [151]. Electrocarboxylation of N-methyldiglycolimide to