Molecular recognition of surface-immobilized carbohydrates by a synthetic lectin

• Melanie Rauschenberg,
• Eva-Corrina Fritz,
• Christian Schulz,
• Tobias Kaufmann and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2014, 10, 1354–1364, doi:10.3762/bjoc.10.138

• inverted research microscope CKX41 (Olympus, Shinjuku, Tokyo/Japan) equipped with a mercury burner U-RFL-T as light source and a DX 20 L-FW camera (Kappa opto-electronics GmbH, Gleichen/Germany) for image acquisition. The camera was controlled by the program Kappa CameraControl (version 2.7.5.7032). All

Nonanebis(peroxoic acid): a stable peracid for oxidative bromination of aminoanthracene-9,10-dione

• Vilas Venunath Patil and
• Ganapati Subray Shankarling

Beilstein J. Org. Chem. 2014, 10, 921–928, doi:10.3762/bjoc.10.90

• (Universal V4.5A TA Instrument), ramp 10.00 °C/min to 300.00 °C, flow rate: 50.0 mL/min. Procedure for the preparation of nonanebis(peroxoic acid): In 250 mL round bottomed flask equipped with a mercury sealed stirrer, 10 g of nonanedioic acid (0.0531 mol) was dissolved in 95% sulfuric acid (25 g, 0.255 mol

• product (9.2 g, 78% yield). The active oxygen content of the final product was determined by iodometric titration. (Reported: 14.5%; Obtained: 14.2–14.4%.) General procedure for oxidative bromination of aminoanthracene-9,10-dione: In a 100 mL round bottomed flask equipped with a mercury sealed stirrer, 5

Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine

• Fei Wang,
• Lingchun Li,
• Chuanfa Ni and
• Jinbo Hu

Beilstein J. Org. Chem. 2014, 10, 344–351, doi:10.3762/bjoc.10.32

• examples include using bis(trifluoromethyl)mercury (Hg(CF3)2) under the promotion of NaI (Scheme 1, reaction 3) [24] and using methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (MDFA) under the promotion of KI (Scheme 1, reaction 4) [25]. Our group has focused on the development and application of new

The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids

• Tatyana L. Pavlovskaya,
• Fedor G. Yaremenko,
• Victoria V. Lipson,
• Svetlana V. Shishkina,
• Oleg V. Shishkin,
• Vladimir I. Musatov and
• Alexander S. Karpenko

Beilstein J. Org. Chem. 2014, 10, 117–126, doi:10.3762/bjoc.10.8

• spectra were recorded on Varian Mercury VX-200 (200 MHz) and Bruker Avance DRX-500 (500 MHz) instruments in DMSO-d6 with TMS as an internal standard. The 13C NMR spectra were recorded on a Bruker Avance DRX-500 (125 MHz) and Bruker AM-300 (75 MHz) instruments in DMSO-d6 with TMS as an internal standard

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

• Alexander O. Terent'ev,
• Dmitry A. Borisov,
• Vera A. Vil’ and
• Valery M. Dembitsky

Beilstein J. Org. Chem. 2014, 10, 34–114, doi:10.3762/bjoc.10.6

• )) with Et2NH in CF3CH2OH. However, these attempts failed. Spiroperoxide 241 was prepared in satisfactory yield by reaction of 240 with the use of mercury (II) acetate (Scheme 68) [331]. The intermediate mercury-containing peroxide produced by the cyclization of bis(hydroperoxide) 240 was reduced with

Charge-transfer interaction mediated organogels from 18β-glycyrrhetinic acid appended pyrene

• Jun Hu,
• Jindan Wu,
• Qian Wang and
• Yong Ju

Beilstein J. Org. Chem. 2013, 9, 2877–2885, doi:10.3762/bjoc.9.324

• used. UV–vis spectra were measured on an Agilent Technologies 95-03 spectrometer; fluorescence spectra were measured on a Varian Cary Eclipse spectrometer; NMR spectra were recorded on Varian Mercury 300/400 spectrometers in CDCl3 and DMSO-d6; mass spectrometry was measured on a Micromass QTOF and

New syntheses of 5,6- and 7,8-diaminoquinolines

• Maroš Bella and
• Viktor Milata

Beilstein J. Org. Chem. 2013, 9, 2669–2674, doi:10.3762/bjoc.9.302

• [Normasil 60 (43–60 μm)]. Melting points were measured on a Koffler block and are uncorrected. 1H NMR and 13C NMR spectra were recorded on a Varian Mercury 300 MHz spectrometer at 25 °C. The operating frequencies were 300 MHz for 1H and 75.5 MHz for 13C nuclei. Chemical shifts (δ) are reported in ppm and

A combined continuous microflow photochemistry and asymmetric organocatalysis approach for the enantioselective synthesis of tetrahydroquinolines

• Erli Sugiono and
• Magnus Rueping

Beilstein J. Org. Chem. 2013, 9, 2457–2462, doi:10.3762/bjoc.9.284

• placed in a water bath [39]. The light required to perform the reaction is supplied from a high-pressure mercury lamp located outside of the reactor. The lamp consists of a double-jacketed water-cooled pyrex immersion well. The reagents were degassed and introduced into the microreactor using a

Temperature measurements with two different IR sensors in a continuous-flow microwave heated system

• Jonas Rydfjord,
• Fredrik Svensson,
• Magnus Fagrell,
• Jonas Sävmarker,
• Måns Thulin and
• Mats Larhed

Beilstein J. Org. Chem. 2013, 9, 2079–2087, doi:10.3762/bjoc.9.244

• than the walls [8]. Unfortunately, under microwave radiation the usual methods to directly measure the internal liquid temperature of a reaction mixture such as thermocouples or mercury thermometers are affected by the electromagnetic field and will thus not be possible to use in the radiated zone [14

Continuous flow photocyclization of stilbenes – scalable synthesis of functionalized phenanthrenes and helicenes

• Quentin Lefebvre,
• Marc Jentsch and
• Magnus Rueping

Beilstein J. Org. Chem. 2013, 9, 1883–1890, doi:10.3762/bjoc.9.221

• tightly wrapped around the water-cooling unit (Duran glass) of a high-pressure mercury lamp (TQ 150, UV-Consulting Peschl). Further optimization and scope was performed with a similar setup using a bigger capillary (FEP, outer/inner diameter 4/2 mm, total volume 24 mL). For the sake of safety and to

Topochemical control of the photodimerization of aromatic compounds by γ-cyclodextrin thioethers in aqueous solution

• Hai Ming Wang and
• Gerhard Wenz

Beilstein J. Org. Chem. 2013, 9, 1858–1866, doi:10.3762/bjoc.9.217

• inclusion complexes were transferred into 50 mL quartz round-bottomed flasks and bubbled with nitrogen gas for 20 min with stirring before photo-irradiation. Photodimerization of the samples was carried out using a medium-pressure mercury lamp (166.5 W, Heraeus Noblelight GmbH, UVB) as a light source. After

[3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions

• Stephan Cludius-Brandt,
• Lukas Kupracz and
• Andreas Kirschning

Beilstein J. Org. Chem. 2013, 9, 1745–1750, doi:10.3762/bjoc.9.201

• water-cooled quartz immersion well (type UV-RS-1, Heraeus) equipped with a medium-pressure mercury lamp (type TQ 150, λ = 190–600 nm). The reaction mixture was fed into the tubing by using a pump and collected in a flask after having passed through the reactor. In essence 2H-azirines can be prepared

A reductive coupling strategy towards ripostatin A

• Kristin D. Schleicher and
• Timothy F. Jamison

Beilstein J. Org. Chem. 2013, 9, 1533–1550, doi:10.3762/bjoc.9.175

• alternative promoters were investigated to avoid the use of mercury(II) salts in the ketal deprotection (including MeI, H2O2, AgClO4/I2); however, these generally led to concomitant removal of the TBS groups. Ketone 19 was converted to the α,β-unsaturated ester 20 using the Peterson olefination [32

α-Bromodiazoacetamides – a new class of diazo compounds for catalyst-free, ambient temperature intramolecular C–H insertion reactions

• Åsmund Kaupang and
• Tore Bonge-Hansen

Beilstein J. Org. Chem. 2013, 9, 1407–1413, doi:10.3762/bjoc.9.157

• ][27][28][29][30], as well as carbon, e.g., in aldol reactions with aldehydes [31][32], ketones [33][34] and imines [35][36]. The first syntheses of α-halodiazoacetic esters, reported in the late 1960s, employed electrophilic diazoalkane substitution; the mercury or silver salts of ethyl diazoacetate

• reflux: a reaction that plausibly occurs with a free halocarbonylcarbene or a mercury carbenoid as intermediate [45][55][56]. In the case of the α-bromo-β-lactam 5b, the authors reported an exo-diastereoselectivity of 5.25:1. In order to compare the reactivity of other halides in the α-position, we

Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review

• Lucio Melone and
• Carlo Punta

Beilstein J. Org. Chem. 2013, 9, 1296–1310, doi:10.3762/bjoc.9.146

• /1. These results are objects of two patent applications [60][61]. Light-induced activation The first example of light-induced in situ generation of PINO radical was reported in 2007 by Lucarini and co-workers [62]. Irradiation of N-alkoxyphthalimides with filtered light (λ > 300 nm) from a mercury

Interplay of ortho- with spiro-cyclisation during iminyl radical closures onto arenes and heteroarenes

• Roy T. McBurney and
• John C. Walton

Beilstein J. Org. Chem. 2013, 9, 1083–1092, doi:10.3762/bjoc.9.120

• Manchester. Oxime carbonates (2 to 15 mg) and MAP (1 equiv wt/wt) in t-BuPh or benzene (0.5 mL) were prepared in quartz tubes and deaerated by bubbling with nitrogen for 15 min. Photolysis in the resonant cavity was by unfiltered light from a 500 W super-pressure mercury arc lamp or, in the Manchester

Spectroscopic characterization of photoaccumulated radical anions: a litmus test to evaluate the efficiency of photoinduced electron transfer (PET) processes

• Maurizio Fagnoni,
• Stefano Protti,
• Davide Ravelli and
• Angelo Albini

Beilstein J. Org. Chem. 2013, 9, 800–808, doi:10.3762/bjoc.9.91

• deoxygenated solutions, except where otherwise noted. The examined solutions were irradiated on an optical bench equipped with a 150 W high-pressure mercury lamp, (λIRR = 313 nm). The electrochemical properties of TCB [8][9], DCN [8][9], DCA [8][9], DCP [10], DCP-ME [10], ME [45], PME [28], Et3N [60], iPr3N

High-spin intermediates of the photolysis of 2,4,6-triazido-3-chloro-5-fluoropyridine

• Sergei V. Chapyshev,
• Denis V. Korchagin,
• Patrik Neuhaus and
• Wolfram Sander

Beilstein J. Org. Chem. 2013, 9, 733–742, doi:10.3762/bjoc.9.83

• were irradiated with a high-pressure mercury lamp, by using a filter passing the light at λ = 260–320 nm, and spectra were recorded at various irradiation times. The computer simulations of EPR spectra were performed by using the EasySpin program package (version 4.0.0) [38]. The simulations were

Quantification of N-acetylcysteamine activated methylmalonate incorporation into polyketide biosynthesis

• Stephan Klopries,
• Uschi Sundermann and
• Frank Schulz

Beilstein J. Org. Chem. 2013, 9, 664–674, doi:10.3762/bjoc.9.75

• 5% aqueous NaOH in 500 mL H2O) and subsequent heat treatment. NMR spectra were recorded by using a Varian Mercury 400 (400 MHz, 1H; 100 MHz, 13C) spectrometer and calibrated using residual undeuterated solvent as an internal reference. High-resolution mass spectra were recorded at LTQ Orbitrap with

Synthesis and stability study of a new major metabolite of γ-hydroxybutyric acid

• Ida Nymann Petersen,
• Jesper Langgaard Kristensen,
• Christian Tortzen,
• Torben Breindahl and
• Daniel Sejer Pedersen

Beilstein J. Org. Chem. 2013, 9, 641–646, doi:10.3762/bjoc.9.72

• . Thin-layer chromatography (TLC) was carried out on commercially available precoated aluminium sheets (Merck 60 F254). The quoted Rf values are rounded to the nearest 0.05. 1H and 13C NMR was run on a Varian Mercury 300 MHz, a Varian Gemini 300 MHz and a Bruker 500 MHz Avance III Fourier transform NMR

Easy and direct conversion of tosylates and mesylates into nitroalkanes

• Alessandro Palmieri,
• Serena Gabrielli and
• Roberto Ballini

Beilstein J. Org. Chem. 2013, 9, 533–536, doi:10.3762/bjoc.9.58

• methodology [42]. 1H NMR was recorded at 400 MHz on a Varian Mercury Plus 400. 13C NMR was recorded at 100 MHz. Microanalyses were performed with a CHNS-O analyser Model EA 1108 from Fisons Instruments. Mass spectra were performed with a GC–MS system Agilent Technologies 6850 II/5973 Inert by means of the EI

Tandem aldehyde–alkyne–amine coupling/cycloisomerization: A new synthesis of coumarins

• Maddi Sridhar Reddy,
• Nuligonda Thirupathi and
• Madala Haribabu

Beilstein J. Org. Chem. 2013, 9, 180–184, doi:10.3762/bjoc.9.21

• transition-metal catalysts (based on gold, mercury, platinum, silver, etc.), Brønsted acids and electrophilic iodine sources (I2, ICl, NIS) have been used for the transformation. If one of the partners in A3 coupling has any nucleophile for concomitant electrophilic cyclization on the alkyne group in the A3

A bisazobenzene crosslinker that isomerizes with visible light

• Subhas Samanta,
• Harris I. Qureshi and
• G. Andrew Woolley

Beilstein J. Org. Chem. 2012, 8, 2184–2190, doi:10.3762/bjoc.8.246

• ) were used as received. NMR spectra were recorded either on Varian Vnmr-S 400 MHz, Varian Mercury 400 MHz or Agilent DD2 500 MHz spectrometers. Silica gel of particle size 40–63 μm from Silicycle Chemical Division was used for column chromatography. Synthesis of 1,4-diphenylpiperazine (7) [34]: A

Flow photochemistry: Old light through new windows

• Jonathan P. Knowles,
• Luke D. Elliott and
• Kevin I. Booker-Milburn

Beilstein J. Org. Chem. 2012, 8, 2025–2052, doi:10.3762/bjoc.8.229

• -well photoreactor in conjunction with mercury-vapour-discharge lamps (Figure 1). This compact batch reactor is an excellent device to carry out preparative photochemistry on scales of milligrams up to a few grams. The lamp is contained in a double-jacketed water-cooled immersion well. This is then

• monitored by conventional means (TLC, GC, LCMS). As often no reagents are used, workup is by simple evaporation of solvent, and the product is purified by conventional means. The most common UV sources are the commercially available mercury-discharge lamps. These are evacuated glass tubes containing mercury

• know-how, e.g., which lamp, glassware and solvent to use. • Safety. Medium pressure mercury lamps operate optimally at ~600 °C and emit intense and potentially damaging UV radiation. • Difficulty in scaling up. The Toray caprolactam process proves this is not a problem at the industrial scale. However

The chemistry of bisallenes

• Henning Hopf and
• Georgios Markopoulos

Beilstein J. Org. Chem. 2012, 8, 1936–1998, doi:10.3762/bjoc.8.225

• mercury-arc lamp or heating (250 °C, benzene), is converted quantitatively to 88, which is presumably the thermodynamically most stable of the C6(TMS)6-isomers (Scheme 22) [73]. West and Priesner obtained 88 as one of the products produced when 2,4-hexadiyne was first metalated by the n-butyllithium/TMEDA