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Search for "benzophenone" in Full Text gives 157 result(s) in Beilstein Journal of Organic Chemistry.

Solvent-free, visible-light photocatalytic alcohol oxidations applying an organic photocatalyst

  • Martin Obst and
  • Burkhard König

Beilstein J. Org. Chem. 2016, 12, 2358–2363, doi:10.3762/bjoc.12.229

Graphical Abstract
  • (m, 4H, CH), 7.30 (m, 2H, CH); EIMS m/z: 180.0579 [M]+. Benzophenone (3b) 3b from 3a: Diphenylmethanol (73.3 mg, 0.40 mmol) and RFTA (10.9 mg, 0.020 mmol) were weighed and 74.0 mg of the mixture was used for reaction. Yield: 50%. 1H NMR (300 MHz, CDCl3) 7.83–7.79 (m, 2H, CH), 7.62–7.57 (m, 2H, CH
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Published 09 Nov 2016

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

  • Forrest S. Etheridge,
  • Roshan J. Fernando,
  • Sandra Pejić,
  • Matthias Zeller and
  • Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

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  • solvents were used as received unless otherwise specified. Xylenes and tetrahydrofuran were distilled over sodium and benzophenone, degassed and stored under nitrogen. ADP, ADPI2, WS3, BF2(WS3), and Zn(WS3)2 were synthesized and purified according to literature procedures with minor modifications [2][5][9
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Published 29 Aug 2016

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

Graphical Abstract
  • light. The latter involves energy transfer from the photosensitizer triplet excited state to ground state molecular oxygen [5][6]. Ketoprofen (KP) is a nonsteroidal anti-inflammatory drug that contains the benzophenone (BZP, Figure 1) chromophore and displays a n,π triplet excited state [7][8][9
  • determined in dichloromethane solutions using the same absorbance value (0.30) at 308 nm for each compound. A singlet oxygen quantum yield (ΦΔ) of 0.95 for perinaphthenone in dichloromethane was used as standard [22]. Chemical structure of the photosensitizing chromophores benzophenone (BZP) and 2
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Published 14 Jun 2016

Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives

  • Phil M. Pithan,
  • David Decker,
  • Manlio Sutero Sardo,
  • Giampietro Viola and
  • Heiko Ihmels

Beilstein J. Org. Chem. 2016, 12, 854–862, doi:10.3762/bjoc.12.84

Graphical Abstract
  • obvious relationship. This behavior is in agreement with that of other donor–acceptor biaryl-type dyes, such as for example para-hetaryl-substituted benzophenone derivatives, whose emission properties were demonstrated to depend on a complex interplay of different solvent parameters [38]. Unfortunately
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Published 02 May 2016

Opportunities and challenges for direct C–H functionalization of piperazines

  • Zhishi Ye,
  • Kristen E. Gettys and
  • Mingji Dai

Beilstein J. Org. Chem. 2016, 12, 702–715, doi:10.3762/bjoc.12.70

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  • on the distal nitrogen atom is likely preventing this nitrogen from attacking the electrophile and triggers an elimination process which would yield a byproduct like 29. Of particular interest, when benzophenone (Ph2CO) was used to trap the α-lithiation product of N-Boc-N’-alkylpiperazines, in
  • addition to the desired products (18, 34, and 35), a significant amount of oxidized product 36 was obtained (Figure 9). The formation of this byproduct is proposed to be a sequential single-electron oxidation of the alkyllithium intermediate by benzophenone. Again, the use of a bulky alkyl group on the
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Published 13 Apr 2016

Iron complexes of tetramine ligands catalyse allylic hydroxyamination via a nitroso–ene mechanism

  • David Porter,
  • Belinda M.-L. Poon and
  • Peter J. Rutledge

Beilstein J. Org. Chem. 2015, 11, 2549–2556, doi:10.3762/bjoc.11.275

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  • commercially available reagents were used without purification unless otherwise specified. Solvents for extraction and chromatography were distilled before use. Solvents for reactions were freshly distilled immediately prior to use. Tetrahydrofuran (THF) was dried over sodium wire and benzophenone
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Published 11 Dec 2015

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

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  • photogenerated copper(I) being very reactive. On irradiating aqueous reaction mixtures containing 1 mol % of 1 at 365 nm (TLC lamp) for 1 h, click reactions were shown to proceed to full conversion. Keywords: benzophenone photosensitizer; bioconjugation; click chemistry; copper; photoreduction; Introduction
  • tren (tren = tris(2-aminoethyl)amine) ligand derivative [11][12] or the dmeda (dmeda = N,N’-dimethylethylenediamine) ligand [13][14] (Scheme 1). Irradiation at 365 nm of the benzophenone photosensitizer (n→π* electronic transition), introduced through the carboxylate counterion, mediated a highly
  • molecules being most probably bound to the copper ions in aqueous solution, while in THF, the carboxylates interact more tightly with the copper ions. This is in agreement with the 1H NMR spectra of 1, which showed well resolved peaks for the benzophenone protons in D2O, while in THF-d8 broad resonances
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Published 21 Oct 2015

Synthesis and structures of ruthenium–NHC complexes and their catalysis in hydrogen transfer reaction

  • Chao Chen,
  • Chunxin Lu,
  • Qing Zheng,
  • Shengliang Ni,
  • Min Zhang and
  • Wanzhi Chen

Beilstein J. Org. Chem. 2015, 11, 1786–1795, doi:10.3762/bjoc.11.194

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  • substituents (Table 2, entries 3–8) and electron-donating groups (Table 2, entries 9 and 10), and the target product could be obtained in excellent yields (90–99%). Bulkier aromatic ketone benzophenone is also tested in this reaction with 92% and 94% conversion after 3 h (Table 2, entries 11 and 12). In
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Published 30 Sep 2015

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

Graphical Abstract
  • standard procedures and were degassed by freeze–thaw cycles prior to use. All chemicals used were purchased from Sigma-Aldrich and used as received. The deuterated solvents were dried with sodium/benzophenone and vacuum transferred for storage in Schlenk flasks fitted with Teflon valves. 1H NMR, 13C{1H
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Published 17 Sep 2015

Grubbs–Hoveyda type catalysts bearing a dicationic N-heterocyclic carbene for biphasic olefin metathesis reactions in ionic liquids

  • Maximilian Koy,
  • Hagen J. Altmann,
  • Benjamin Autenrieth,
  • Wolfgang Frey and
  • Michael R. Buchmeiser

Beilstein J. Org. Chem. 2015, 11, 1632–1638, doi:10.3762/bjoc.11.178

Graphical Abstract
  • , Netherlands) and were dried by using an MBraun SPS-800 solvent purification system. Hexane was purchased from VWR and distilled from sodium/benzophenone under N2. Starting materials were purchased from ABCR, Aldrich, Alfa Aesar, Fluka and TCI Europe and used without further purification. KOCMe2Et was
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Published 15 Sep 2015

Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium–zinc base and regioselectivity-computed CH acidity relationship

  • Mohamed Yacine Ameur Messaoud,
  • Ghenia Bentabed-Ababsa,
  • Madani Hedidi,
  • Aïcha Derdour,
  • Floris Chevallier,
  • Yury S. Halauko,
  • Oleg A. Ivashkevich,
  • Vadim E. Matulis,
  • Laurent Picot,
  • Valérie Thiéry,
  • Thierry Roisnel,
  • Vincent Dorcet and
  • Florence Mongin

Beilstein J. Org. Chem. 2015, 11, 1475–1485, doi:10.3762/bjoc.11.160

Graphical Abstract
  • reason [37][38][40], the corresponding N-(4-substituted phenyl)pyrroles and -indoles are rather functionalized at C3’, next to the substituent. Experimental General methods. All the reactions were performed under argon atmosphere. THF was distilled over sodium/benzophenone. ZnCl2·TMEDA was prepared as
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Published 24 Aug 2015

Design and synthesis of fused polycycles via Diels–Alder reaction and ring-rearrangement metathesis as key steps

  • Sambasivarao Kotha and
  • Ongolu Ravikumar

Beilstein J. Org. Chem. 2015, 11, 1259–1264, doi:10.3762/bjoc.11.140

Graphical Abstract
  • -sensitive reagents or catalysts were performed in degassed solvents. Dry tetrahydrofuran (THF) and dry ether were obtained by distillation over sodium benzophenone ketyl freshly prior to use. Dichloromethane (DCM) and toluene were distilled over P2O5 and DMF over CaH2. Sodium sulfate was dried in an oven at
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Published 27 Jul 2015

Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

  • Huixin Jiang,
  • Virginia Mazzanti,
  • Christian R. Parker,
  • Søren Lindbæk Broman,
  • Jens Heide Wallberg,
  • Karol Lušpai,
  • Adam Brincko,
  • Henrik G. Kjaergaard,
  • Anders Kadziola,
  • Peter Rapta,
  • Ole Hammerich and
  • Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2015, 11, 930–948, doi:10.3762/bjoc.11.104

Graphical Abstract
  • -radiaannulenes exhibit low-energy CT absorptions. Experimental General Methods – Synthesis. Chemicals were purchased from Aldrich, Fluka, and GSF Chemicals and used as received. THF was distilled over the Na/benzophenone couple. Solvents were of HPLC grade and used as received. Thin layer chromatography (TLC
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Published 02 Jun 2015

Probing multivalency in ligand–receptor-mediated adhesion of soft, biomimetic interfaces

  • Stephan Schmidt,
  • Hanqing Wang,
  • Daniel Pussak,
  • Simone Mosca and
  • Laura Hartmann

Beilstein J. Org. Chem. 2015, 11, 720–729, doi:10.3762/bjoc.11.82

Graphical Abstract
  • -functionalized SCPs. Carboxy groups on the SCP were introduced by a radical grafting process where incubation of the PEG microgels with benzophenone and acrylic acid lead to poly(acrylic acid) grafts on the PEG backbone. Using this model system, we could already show that the mechanical flexibility of the
  • (Scheme 1). It is known that benzophenone can absorb the energy of photons to excite the electron in its carbonyl group from ground state (S0) to the excited state (S1) or (S2) depending on the wavelength used. Subsequently, the excited electron can go to the triple state (T1) through intersystem crossing
  • (ISC). At the T1 state, the benzophenone molecule has an excited electron which is highly reactive, and can abstract a hydrogen atom from the PEG backbone. The abstracted hydrogen atom generates a radical on the PEG-backbone and a semipinacol radical on the benzophenone carbonyl group [16]. In the
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Published 12 May 2015

Trifluoromethyl-substituted tetrathiafulvalenes

  • Olivier Jeannin,
  • Frédéric Barrière and
  • Marc Fourmigué

Beilstein J. Org. Chem. 2015, 11, 647–658, doi:10.3762/bjoc.11.73

Graphical Abstract
  • from Na/benzophenone. CH3CN and CH2Cl2 were distilled over P2O5 and MeOH over Mg/I2. Column chromatography was performed on silica gel. 1H, 13C and 19F NMR spectra were obtained on a Bruker Avance DRX500 spectrometer at 500.04 MHz for 1H, 470.28 MHz for 19F and 125.75 MHz for 13C. Chemical shifts were
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Published 06 May 2015

Photocatalytic nucleophilic addition of alcohols to styrenes in Markovnikov and anti-Markovnikov orientation

  • Martin Weiser,
  • Sergej Hermann,
  • Alexander Penner and
  • Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2015, 11, 568–575, doi:10.3762/bjoc.11.62

Graphical Abstract
  • °C, using a 250 mW high-power LED (λ = 530 nm) as light source while stirring. Preliminary experiments with substrate 1 revealed that formation of benzophenone was nearly completely prevented by carefully degassing the reaction mixture. A previous report of Neunteufel and Arnold considered the
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Published 27 Apr 2015

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

Graphical Abstract
  • direct conjugation, whereby a third such system is excluded from interaction [3]. Typical examples are 2-vinyl-buta-1,3-diene ([3]dendralene, 3-methylene-penta-1,4-diene), benzophenone or urea. Whereas the hydrocarbon parent systems, the [n]dendralenes, have long been a neglected class of oligoenes [4
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Published 18 Mar 2015

An unusually stable chlorophosphite: What makes BIFOP–Cl so robust against hydrolysis?

  • Roberto Blanco Trillo,
  • Jörg M. Neudörfl and
  • Bernd Goldfuss

Beilstein J. Org. Chem. 2015, 11, 313–322, doi:10.3762/bjoc.11.36

Graphical Abstract
  • application as a chiral ligand to be used in, for example, Pd catalysis [13][14][15]. Experimental All reactions were carried out under an inert argon atmosphere and in heated glassware using standard Schlenk techniques. Anhydrous solvents were obtained by distillation from sodium benzophenone ketyl. The NMR
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Published 04 Mar 2015

(2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues

  • Armin de Meijere,
  • Sergei I. Kozhushkov,
  • Dmitrii S. Yufit,
  • Christian Grosse,
  • Marcel Kaiser and
  • Vitaly A. Raev

Beilstein J. Org. Chem. 2014, 10, 2844–2857, doi:10.3762/bjoc.10.302

Graphical Abstract
  • -threonine (4) and (2S,3R)-β-methylphenylalanine (3), using the Belokon' approach with (S)- and (R)-2-[(N-benzylprolyl)amino]benzophenone [(S)- and (R)-10] as reusable chiral auxiliaries have been developed. Three new fluoromethyl analogues of the naturally occurring octadepsipeptide hormaomycin (1) with
  • from (S)- and (R)-2-[(N-benzylprolyl)amino]benzophenone [(S)- and (R)-10] as reusable chiral auxiliaries with the racemic iodides 11a–c, employing the protocol of Larionov and de Meijere [7], in each case led to a mixture of diastereomeric products, which were separated by column chromatography
  • corresponding (2S,1'S,2'R)- [see Scheme 3, derived from (S)-10] and (2R,1'S,2'R)-3-(2'-fluoromethylcyclopropyl)alanines [derived from (R)-10] in good to excellent yields. The chiral auxiliary was recovered as the hydrochloride of 2-[(N-benzylprolyl)amino]benzophenone (~95%). (R)-allo-Threonine (4) is
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Published 03 Dec 2014

Design and synthesis of novel bis-annulated caged polycycles via ring-closing metathesis: pushpakenediol

  • Sambasivarao Kotha and
  • Mirtunjay Kumar Dipak

Beilstein J. Org. Chem. 2014, 10, 2664–2670, doi:10.3762/bjoc.10.280

Graphical Abstract
  • nitrogen by using oven-dried glassware and syringes. THF and Et2O were distilled from sodium/benzophenone under nitrogen immediately prior to use. Dichloromethane was distilled over P2O5. TLC was performed by using (10 × 5 cm) glass plates coated with Acme’s silica gel GF254 (containing 13% calcium sulfate
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Published 13 Nov 2014

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

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  • was first described by Wawzonek, converting benzophenone and acetophenone to benzylic acid and 2-hydroxy-2-phenylpropionic acid, respectively [79]. This offers an electrochemical route for several commercially relevant α-aryl propionic acids, used as non-steroidal anti-inflammatory drugs (NSAIDs) [80
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Published 27 Oct 2014

Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing

  • Bradley D. Rose,
  • Peter J. Santa Maria,
  • Aaron G. Fix,
  • Chris L. Vonnegut,
  • Lev N. Zakharov,
  • Sean R. Parkin and
  • Michael M. Haley

Beilstein J. Org. Chem. 2014, 10, 2122–2130, doi:10.3762/bjoc.10.219

Graphical Abstract
  • the UV–vis spectrum (Table 3). To see if this was a computational artifact, the same calculations were performed for fluorenone and benzophenone, where it has previously been established that the S0→S1 transition corresponds to π→π* and n→π*, respectively [29][30]. The calculations correctly predict
  • the ordering of the states for fluorenone and benzophenone. To validate this experimentally, UV–vis spectra were gathered in solvents of differing polarity. We anticipated that if the S0→S1 transition corresponds to a n→π* transition, the energy separating the S0 and S1 states would be measurably
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Published 05 Sep 2014

Photorelease of phosphates: Mild methods for protecting phosphate derivatives

  • Sanjeewa N. Senadheera,
  • Abraham L. Yousef and
  • Richard S. Givens

Beilstein J. Org. Chem. 2014, 10, 2038–2054, doi:10.3762/bjoc.10.212

Graphical Abstract
  • triplet sensitized photolysis in the presence of benzophenone (BP), a well-established triplet sensitizer, at 254 nm under O2-free conditions was Φdis = 0.022. These combined results demonstrate that the reactive excited state is a triplet that is partially quenched by O2 under ambient conditions
  • disappearance quantum efficiency (Table 2). 4. Triplet sensitization experiment. A quartz tube was charged with 14a (2.0 mg, 0.0059 mmol) and benzophenone (20 mg, 0.11 mmol), and the contents were dissolved in acetonitrile (10 mL) to which was added water (100 µL) to make a 1% aqueous solution. The solution was
  • degassed with argon and irradiated with 6-RPR 2540 Å bulbs. Sample aliquots (0.2 mL) were taken after 0, 2, 5, 7, and 10 min of photolysis and analyzed by HPLC on a C18 analytical column with a mobile phase containing 70% acetonitrile and 30% water. The detection wavelength was 323 nm. The benzophenone had
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Published 29 Aug 2014

An economical and safe procedure to synthesize 2-hydroxy-4-pentynoic acid: A precursor towards ‘clickable’ biodegradable polylactide

  • Quanxuan Zhang,
  • Hong Ren and
  • Gregory L. Baker

Beilstein J. Org. Chem. 2014, 10, 1365–1371, doi:10.3762/bjoc.10.139

Graphical Abstract
  • methods All reactions, if not stated otherwise, were performed in oven-dried glassware under nitrogen atmosphere. THF and dioxane were dried over sodium/benzophenone and distilled before use. All other reagents and solvents were ACS grade and used as received unless specified. Melting points were measured
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Published 17 Jun 2014

Homochiral BINOL-based macrocycles with π-electron-rich, electron-withdrawing or extended spacing units as receptors for C60

  • Marco Caricato,
  • Silvia Díez González,
  • Idoia Arandia Ariño and
  • Dario Pasini

Beilstein J. Org. Chem. 2014, 10, 1308–1316, doi:10.3762/bjoc.10.132

Graphical Abstract
  • ], 3a [28], 4a [28] and p-toluenesulfonic acid 4-dimethylaminopyridinium salt (PTSA-DMAP) [45] were prepared according to literature procedures. THF (Na, benzophenone) and CH2Cl2 (CaH2) were dried before use. Analytical thin-layer chromatography was performed on silica gel, chromophore loaded, and with
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Published 06 Jun 2014
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