Is the tungsten(IV) complex (NEt₄)₂[WO(mnt)₂] a functional analogue of acetylene hydratase?

• Matthias Schreyer and
• Lukas Hintermann

Beilstein J. Org. Chem. 2017, 13, 2332–2339, doi:10.3762/bjoc.13.230

• reaction mechanism of acetylene hydratase [10][11][12]. c) Tungsten complex (NEt4)2[WO(mnt)2] (1), which was reported as acetylene hydration catalyst [13]. a) π-Activation pathway in Markovnikov selective alkyne hydration, e.g., with mercury catalysts. b) Ruthenium-catalyzed anti-Markovnikov hydration via

The effect of milling frequency on a mechanochemical organic reaction monitored by in situ Raman spectroscopy

• Patrick A. Julien,
• Ivani Malvestiti and
• Tomislav Friščić

Beilstein J. Org. Chem. 2017, 13, 2160–2168, doi:10.3762/bjoc.13.216

• on a 300 MHz Varian Mercury spectrometer. The ambient temperature was measured using a digital thermometer by VWR and the internal jar temperature was acquired immediately after milling finished using a Mastercraft Temperature Reader with Digital Display and Laser Pointer (accuracy ±2 °C). Time

Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound

• Joana M. Pais,
• Maria João Barroca,
• Maria Paula M. Marques,
• Filipe A. Almeida Paz and
• Susana S. Braga

Beilstein J. Org. Chem. 2017, 13, 2138–2145, doi:10.3762/bjoc.13.212

• inclusion compound γ-CD–12-crown-4 ether [31] using the software Mercury 3.5.1 (copyright CCDC 2001–2014). The inset depicts the structure of γ-CD–12-crown-4 ether, as viewed from the top (crystallographic c-axis) and from the sides (crystallographic a-axis). 13C{1H} CP/MAS NMR spectra for (a) fisetin, (b

Enzymatic separation of epimeric 4-C-hydroxymethylated furanosugars: Synthesis of bicyclic nucleosides

• Neha Rana,
• Manish Kumar,
• Vinod Khatri,
• Jyotirmoy Maity and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2017, 13, 2078–2086, doi:10.3762/bjoc.13.205

• using the WinGX package of the crystallographic programs [21]. For the molecular graphics, the programs DIAMOND-2 [22] and Mercury [23][24] were used. Molecular structures have been drawn using ORTEP as software as given in Figure 2 and Figure 3. The selected bond lengths, bond angles, etc. are given in

Correlation of surface pressure and hue of planarizable push–pull chromophores at the air/water interface

• Frederik Neuhaus,
• Fabio Zobi,
• Gerald Brezesinski,
• Marta Dal Molin,
• Stefan Matile and
• Andreas Zumbuehl

Beilstein J. Org. Chem. 2017, 13, 1099–1105, doi:10.3762/bjoc.13.109

• ) equipped with a liquid nitrogen cooled MCT (mercury cadmium telluride) detector attached to an external air/water reflection unit (XA-511). The IR beam was conducted out of the spectrometer and focused onto the water surface of the thermostated Langmuir trough. The measurements were carried out with p- and

Exploring endoperoxides as a new entry for the synthesis of branched azasugars

• Svenja Domeyer,
• Mark Bjerregaard,
• Henrik Johansson and
• Daniel Sejer Pedersen

Beilstein J. Org. Chem. 2017, 13, 644–647, doi:10.3762/bjoc.13.63

• mercury lamp was replaced with three 100 W halogen bulbs. Dihydroxylation and protection of endoperoxides 18 and 19 to provide novel building blocks 20–23 for azasugar synthesis. Preliminary exploration of the chemistry of endoperoxides 18–23 was encouraging and gave access to a variety of derivatives

Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides

• Jan Szabo,
• Julian Greiner and
• Gerhard Maas

Beilstein J. Org. Chem. 2017, 13, 579–588, doi:10.3762/bjoc.13.57

• ) 176(2)°; N4–H···Cl, N4···Cl 3.320(2) Å, NH···Cl 2.53(2) Å, <(N4–H···Cl) 148(2)°. Left: solid-state structure of 9b·H2O (ORTEP plot). Right: centrosymmetric hydrogen-bonded dimer of (CF3SO3)−·H2O (Mercury plot); the substituents at the triazole ring are not complete. Selected bond lengths (Å): C1–N1

Effect of the ortho-hydroxy group of salicylaldehyde in the A³ coupling reaction: A metal-catalyst-free synthesis of propargylamine

• Sujit Ghosh,
• Kinkar Biswas,
• Suchandra Bhattacharya,
• Pranab Ghosh and
• Basudeb Basu

Beilstein J. Org. Chem. 2017, 13, 552–557, doi:10.3762/bjoc.13.53

• ], mercury [26], cobalt [27], iridium [28], ruthenium [29], indium [30] etc. Other methods towards the synthesis of propargylamine include: alkynylation of imine [31][32][33], enamine [34], and Csp³–H bonds adjacent to N-atoms [35][36]. In the A3 coupling, the role of the metal catalyst is believed to

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

• in 98% yield for both THP and MOM ethers (Scheme 62). Irradiation of aromatic γ,δ-epoxy ketones 226 with a medium-pressure UV mercury lamp (450 W) led to the formation of 1-indanones 227 via a photochemical epoxy rearrangement and 1,5-biradical cyclization tandem reaction (Scheme 63) [92]. The best

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

• was studied using an optical bench with medium pressure mercury-vapor lamp of 200 W (Tunsgram, Hungary) emitting mainly in the UV-A range. The light was focused by an optical lens on the quartz cuvette containing the sample. The concentration of MB and IBR was measured by spectrophotometry and by HPLC

A new protocol for the synthesis of 4,7,12,15-tetrachloro[2.2]paracyclophane

• Donghui Pan,
• Yanbin Wang and
• Guomin Xiao

Beilstein J. Org. Chem. 2016, 12, 2443–2449, doi:10.3762/bjoc.12.237

• benzyl brominated product was obtained. This could be explained by the deactivating effect of the nitro group [16]. Therefore, a 100 W high pressure mercury lamp (‘solar’ light) was used to increase the formation of bromide radical in the repeated bromination experiment of 9. On this occasion the yield

β-Amino functionalization of cinnamic Weinreb amides in ionic liquid

• Yi-Ning Wang,
• Guo-Xiang Sun and
• Gang Qi

Beilstein J. Org. Chem. 2016, 12, 2372–2377, doi:10.3762/bjoc.12.231

• aminochlorination reactions were performed in oven-dried vials. Flash column chromatography was performed using silica gel (Merck 60, 230–400 mesh). 1H and 13C NMR spectra were obtained with Varian Inova 500 MHz and Varian Mercury Plus 300 MHz spectrometers using deuterated chloroform as a solvent. Internal TMS (δ

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

• David R. Chisholm,
• Garr-Layy Zhou,
• Ehmke Pohl,
• Roy Valentine and
• Andrew Whiting

Beilstein J. Org. Chem. 2016, 12, 1851–1862, doi:10.3762/bjoc.12.174

• spectra were recorded in CDCl3 using Varian VNMRS-700, Varian VNMRS-600, Bruker Avance-400 or Varian Mercury-400 spectrometers operating at ambient probe temperature. NMR peaks are reported as singlet (s), doublet (d), triplet (t), quartet (q), broad (br), septet (sept), combinations thereof, or as a

Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines

• Adrian E. Ion,
• Liliana Cristian,
• Mariana Voicescu,
• Masroor Bangesh,
• Augustin M. Madalan,
• Daniela Bala,
• Constantin Mihailciuc and
• Simona Nica

Beilstein J. Org. Chem. 2016, 12, 1812–1825, doi:10.3762/bjoc.12.171

• the possible formation of weak hydrogen bonds in this solvent [44]. For both metal ions similar absorption features were observed. Upon addition of HgCl2 solution, the absorption maxima located at 378 nm and 431 nm are merging into a new band at 421 nm upon mercury complex formation. A progressive

• equivalents of the mercury salt to a solution of 4a in CD3OD (38 mM) caused the formation of a precipitate that it is insoluble in the deuterated methanol. Further addition of 0.25 equivalents of HgCl2 afforded a pale yellow solution with a brownish precipitate on the bottom of the NMR tube. After evaporation

• of this solvent, the solid was re-dissolved in DMSO-d6. The comparison with the 1H NMR spectrum of free 4a in the same deuterated solvent shows that the chemical shifts of all terpyridine and azulene protons are downfield shifted upon mercury complex formation (Figure S2, Supporting Information File

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

• energy-saving light bulb (Osram Dulux Superstar). LEDs exhibit high light power (~110 lm W−1) at low energy consumption in comparison with other powerful light sources such as mercury lamps (~50 lm W−1). The availability of various LED types with different wavelengths and narrow emission spectra obviates

The hydrolysis of geminal ethers: a kinetic appraisal of orthoesters and ketals

• Sonia L. Repetto,
• James F. Costello,
• Craig P. Butts,
• Joseph K. W. Lam and
• Norman M. Ratcliffe

Beilstein J. Org. Chem. 2016, 12, 1467–1475, doi:10.3762/bjoc.12.143

• located in the 2014 release of the Cambridge Structural Database (CSD v 5.35, which contains 658, 007 entries) using the Conquest software (v 1.16) and visualised using the Mercury software package (v 3.1). Conformational searching was conducted with Macromodel software, using a MonteCarlo search method

Ring-whizzing in polyene-PtL₂ complexes revisited

• Oluwakemi A. Oloba-Whenu,
• Thomas A. Albright and
• Chirine Soubra-Ghaoui

Beilstein J. Org. Chem. 2016, 12, 1410–1420, doi:10.3762/bjoc.12.135

• Information Supporting Information File 212: The molecular geometry and total electronic energy for the molecules in this work are given in .xyz format. The file may be opened as a text file to read the coordinates, or opened directly by a molecular modeling program such as Mercury (http://www.ccdc.cam.ac.uk

Reactivity studies of pincer bis-protic N-heterocyclic carbene complexes of platinum and palladium under basic conditions

• David C. Marelius,
• Curtis E. Moore,
• Arnold L. Rheingold and
• Douglas B. Grotjahn

Beilstein J. Org. Chem. 2016, 12, 1334–1339, doi:10.3762/bjoc.12.126

• even longer. In 1968, Wanzlick and Öfele separately synthesized mercury(II) and chromium(0) imidazol-2-ylidene complexes [3]. Nearly 50 years of NHC ligand research have demonstrated the importance of the electronic and steric effects that can be modified by altering the alkyl or aryl groups on each

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

• -yl)methyleneamine [17], a N-(1-pyrene)methylideneglucosamine mercury complex [18], a N-(pyren-1-ylidene)-2-hydroxyaniline-copper(II) and -zinc(II) complexes [19] or N-(pyren-1-ylidene)-4-carboxyaniline-Fe(II) and -Cr(III) complexes [20]. Several phosphorus-supported ligands containing a pyrene-1

Biradical vs singlet oxygen photogeneration in suprofen–cholesterol systems

• Fabrizio Palumbo,
• Francisco Bosca,
• Isabel M. Morera,
• Inmaculada Andreu and
• Miguel A. Miranda

Beilstein J. Org. Chem. 2016, 12, 1196–1202, doi:10.3762/bjoc.12.115

• photogeneration of biradicals and 1O2, the key mechanistic steps in Ch photooxidation. Steady-state irradiation of 1 and 2 was performed in dichloromethane, under nitrogen, through Pyrex, using a 400 W medium pressure mercury lamp. The spectral analysis of the separated fractions revealed formation of two

• nitrogen, using a Pyrex filter and a 400 W medium pressure mercury lamp. The reaction progress was followed by TLC and NMR. The resulting photomixtures were submitted to silica gel column chromatography, using hexane/ethyl acetate (95:5 v/v) as eluent. The spectral analysis of the separated fractions

• of (S)- or (R)-α-Ch dyads 1 and 2 (150 mg, 0.24 mmol) were irradiated for 8 h through Pyrex with a 400 W medium pressure mercury lamp. After this time the reaction mixtures were concentrated under reduced pressure, and the photomixtures were submitted to silica gel column chromatography, using hexane

Efficient syntheses of climate relevant isoprene nitrates and (1R,5S)-(−)-myrtenol nitrate

• Sean P. Bew,
• Glyn D. Hiatt-Gipson,
• Graham P. Mills and
• Claire E. Reeves

Beilstein J. Org. Chem. 2016, 12, 1081–1095, doi:10.3762/bjoc.12.103

• of mercury(I) chloride (0.06 mol %) and sulfuric acid (0.35 mol %) in water following the procedure of Boger et al. [51]. 63 was afforded in an unoptimized 78% yield. Employing the conditions outlined in Scheme 10 63 reacted with the stabilized ylide generated from the deprotonation of triethyl

A robust synthesis of 7,8-didemethyl-8-hydroxy-5-deazariboflavin

• Matthias Bender,
• Henrik Mouritsen and
• Jens Christoffers

Beilstein J. Org. Chem. 2016, 12, 912–917, doi:10.3762/bjoc.12.89

• [26]. Diacetonide formation (product 8, 75%) proceeded as reported for the di(ethylthio) congener [24]. Finally, the dithioacetyl was cleaved while the isopropylidene moieties were retained, but not with mercury salts, as in original publications for the preparation of aldehyde 9 [27], but with the

• deprotection with iodine instead of mercury compounds) we have improved the synthesis of aldehyde 9. The latter compound was then transformed to the protected ribitylamine 10 via the oxime, which was reduced with LiAlH4. Primary amine 10 was then converted with chlorouracil 3, which was actually the key

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

• irradiating the base suspended in the solution of 1a with a mercury low-pressure quartz lamp (254 nm) in a quartz reactor with intensive stirring. It was found that the yields of 2a after photolysis of 1a substantially increased in the presence of a base. No dependency on the nature of the base could be

New synthetic strategies for xanthene-dye-appended cyclodextrins

• Milo Malanga,
• Andras Darcsi,
• Mihaly Balint,
• Gabor Benkovics,
• Tamas Sohajda and
• Szabolcs Beni

Beilstein J. Org. Chem. 2016, 12, 537–548, doi:10.3762/bjoc.12.53

• agents for the carboxylic acid were HOBt and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC). Fang and co-workers designed a ratiometric sensor for detecting mercury ions in aqueous media, some biological fluids and living cells based on a rhodamine-modified β-CD [16]. The synthetic strategy was a

A selective and mild glycosylation method of natural phenolic alcohols

• Mária Mastihubová and
• Monika Poláková

Beilstein J. Org. Chem. 2016, 12, 524–530, doi:10.3762/bjoc.12.51

• look for milder conditions for an efficient and inexpensive method of glycosylation while excluding the use of toxic mercury salts as promoter (Helferich reaction) or silver salts. The latter are often rather expensive, moisture and light sensitive, and uncomfortable to handle. Accordingly, various