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

My maize and blue brick road to physical organic chemistry in materials

• Anne J. McNeil

Beilstein J. Org. Chem. 2016, 12, 229–238, doi:10.3762/bjoc.12.24

• , might be gelators. We searched the CSD for molecules containing a mercury atom (Hg2+) that was involved in an intermolecular cation–π interaction [28]. We identified molecule 2a, which exhibited 1D π–cation–π interactions in the solid state (Figure 3). Graduate student Kelsey (King) Carter synthesized

Synthesis of cyclic N¹-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells

• Ahmed Mahal,
• Stefano D’Errico,
• Nicola Borbone,
• Brunella Pinto,
• Agnese Secondo,
• Valeria Costantino,
• Valentina Tedeschi,
• Giorgia Oliviero,
• Vincenzo Piccialli and
• Gennaro Piccialli

Beilstein J. Org. Chem. 2015, 11, 2689–2695, doi:10.3762/bjoc.11.289

• . 1H and 13C NMR experiments were performed using a Varian Mercury Plus 400 MHz spectrometer in CD3OD, D2O, CDCl3 and acetone-d6 solvents. Chemical shifts are reported in parts per million (δ) relative to residual solvents signals: CD2HOD 3.31, HOD 4.80, (CD3)(CD2H)CO 2.09 for 1H NMR and CD3OD 49.0 for

Exploring architectures displaying multimeric presentations of a trihydroxypiperidine iminosugar

• Camilla Matassini,
• Stefania Mirabella,
• Andrea Goti,
• Inmaculada Robina,
• Antonio J. Moreno-Vargas and
• Francesca Cardona

Beilstein J. Org. Chem. 2015, 11, 2631–2640, doi:10.3762/bjoc.11.282

• plates (Merck F254). Column chromatographies were carried out on Silica Gel 60 (32–63 μm) or on silica gel (230–400 mesh, Merck). Yields refer to spectroscopically and analytically pure compounds unless otherwise stated. 1H NMR spectra were recorded on a Varian Mercury-400 or on a Varian INOVA 400

Effective ascorbate-free and photolatent click reactions in water using a photoreducible copper(II)-ethylenediamine precatalyst

• Redouane Beniazza,
• Natalia Bayo,
• Florian Molton,
• Carole Duboc,
• Stéphane Massip,
• Nathan McClenaghan,
• Dominique Lastécouères and
• Jean-Marc Vincent

Beilstein J. Org. Chem. 2015, 11, 1950–1959, doi:10.3762/bjoc.11.211

• mercury lamp (type TLC = thin-layer chromatography, 365 nm), or by a 23 W fluorescent bulb, or by ambient/sunlight. In water, a much poorer hydrogen atom donating solvent, the photoreduction of 1 proved inefficient. Interestingly, EPR studies revealed that complex 1 could nonetheless be effectively

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

• Alexander L. Kanibolotsky,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1749–1766, doi:10.3762/bjoc.11.191

• required for this, 4,6-dibromothieno[3,4-d][1,3]dithiole-2-one (15b), can be efficiently obtained by brominating compound 15a, which in turn is synthesised by mercury(II) acetate assisted transchalcogenation reaction from the corresponding thione 17. Unsubstituted thieno[3,4-d][1,3]dithiole-2-thione (17

A facile synthetic route to benzimidazolium salts bearing bulky aromatic N-substituents

• Gabriele Grieco,
• Olivier Blacque and
• Heinz Berke

Beilstein J. Org. Chem. 2015, 11, 1656–1666, doi:10.3762/bjoc.11.182

• } NMR data were recorded on a Varian Gemini-300, a Varian Mercury 200 or Bruker DRX 500 spectrometer using 5 mm diameter NMR tubes. Chemical shifts are expressed in parts per million (ppm). 1H and 13C{1H} NMR spectra were referenced to the residual proton or 13C resonances of the deuterated solvent

Selected synthetic strategies to cyclophanes

• Sambasivarao Kotha,
• Mukesh E. Shirbhate and
• Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistry

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2015, 11, 1194–1219, doi:10.3762/bjoc.11.134

• -polymer tubing wrapped around a cooled medium pressure mercury lamp was used to efficiently generate and react the singlet oxygen in the presence of tetraphenylporphyrin (TPP) as a photosensitizer. Upon exiting the photoreactor, the reaction stream was acidified by combining with a stream of TFA in order

Cathodic hydrodimerization of nitroolefins

• Michael Weßling and
• Hans J. Schäfer

Beilstein J. Org. Chem. 2015, 11, 1163–1174, doi:10.3762/bjoc.11.131

• 85% to 92% yield at a mercury pool cathode and with slightly lower yields at a graphite cathode [5][6][7][8]. The current controlled reduction of alkyl- and aryl-substituted nitroalkenes in acidic medium affords mixtures of ketones and oximes in yields of 39% to 72% [9] and 55% to 91% [10

• the cathode material mercury against the environmentally benign graphite. At a graphite cathode the nitroolefin 1 could be hydrodimerized to the dimer 2. With 60% the yield is lower than in the reduction at the Hg cathode, where 88% of the dimer were obtained. Possibly higher yields can be obtained

• with other graphite varieties or other nontoxic cathode materials. But in principle the mercury cathode can be replaced by a graphite cathode. Structure of the hydrodimers All products show for the nitro group characteristic asymmetrical and symmetrical vibrations at 1530–1560 cm−1 and 1350–1360 cm−1

New tris- and pentakis-fused donors containing extended tetrathiafulvalenes: New positive electrode materials for rechargeable batteries

• Shintaro Iwamoto,
• Yuu Inatomi,
• Daisuke Ogi,
• Satoshi Shibayama,
• Yukiko Murakami,
• Minami Kato,
• Kazuyuki Takahashi,
• Kazuyoshi Tanaka,
• Nobuhiko Hojo and
• Yohji Misaki

Beilstein J. Org. Chem. 2015, 11, 1136–1147, doi:10.3762/bjoc.11.128

• undesired byproducts. The homo-coupling reaction using 11 might give 12 in a good yield, however, toxic and expensive mercury(II) acetate has to be used for the synthesis of 11. Thus, the cross-coupling reaction is useful for saving 11. The Horner–Wadsworth–Emmons reaction of 12 with 2 equiv of aldehydes