A modular approach to neutral P,N-ligands: synthesis and coordination chemistry

• Vladislav Vasilenko,
• Torsten Roth,
• Clemens K. Blasius,
• Sebastian N. Intorp,
• Hubert Wadepohl and
• Lutz H. Gade

Beilstein J. Org. Chem. 2016, 12, 846–853, doi:10.3762/bjoc.12.83

• have a significant influence on the binding geometry und coordination properties of these bidentate P,N-donors. Keywords: P,N-ligands; phosphanylformamidines; phosphine imines; transition metal complexes; Introduction P,N-ligands have been applied in a wide variety of chemical reactions ranging from

Dynamic behavior of rearranging carbocations – implications for terpene biosynthesis

• Stephanie R. Hare and
• Dean J. Tantillo

Beilstein J. Org. Chem. 2016, 12, 377–390, doi:10.3762/bjoc.12.41

• questions. MD simulations have been employed to answer two different questions about the chemical reactions discussed below: (1) what mechanism(s) is energetically viable? and (2) do (non-statistical) dynamic effects exert control over product distributions? While trajectories can be started from anywhere

Enabling technologies and green processes in cyclodextrin chemistry

• Giancarlo Cravotto,
• Marina Caporaso,
• Laszlo Jicsinszky and
• Katia Martina

Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30

• enantiomeric ratio. Basically, three major types of HSBM chemical reaction can occur in the presence of CDs: Preparation of CD complexes and various chemical reactions on the complexed substructures; Derivatization of naked, natural CD; Reactions of activated CD. While reactions occur between a complexed

Learning from the unexpected in life and DNA self-assembly

• Jennifer M. Heemstra

Beilstein J. Org. Chem. 2015, 11, 2713–2720, doi:10.3762/bjoc.11.292

• chemical reactions [4]. In the context of this project, our unexpected observation regarding the impact of dyes on DNA assembly was something that we merely needed to overcome. However, this experience provided us with an improved understanding of the function of structure-switching sensors, which has

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

• polyolefins can serve as structural models for “polyacetylene”, their chemical properties should also reflect that of the polymer. Chemical reactions of the higher acyclic polyolefins have scarcely been studied, and we hence decided to carry out typical, textbook olefin reactions of a representative selection

Glycoluril–tetrathiafulvalene molecular clips: on the influence of electronic and spatial properties for binding neutral accepting guests

• Yoann Cotelle,
• Marie Hardouin-Lerouge,
• Stéphanie Legoupy,
• Olivier Alévêque,
• Eric Levillain and
• Piétrick Hudhomme

Beilstein J. Org. Chem. 2015, 11, 1023–1036, doi:10.3762/bjoc.11.115

• . The stepwise oxidation of each molecular clip involves an electrochemical mechanism with three one-electron processes and two charge-coupled chemical reactions, a scheme which is supported by electrochemical simulations. The fine-tunable π-donating ability of the TTF units and the cavity size allow to

• by an electrochemical simulation program (DigiElch 7) involving an electrochemical mechanism (Scheme 4) composed by three one-electron processes and two charge-coupled chemical reactions (i.e., formation of mixed-valence and dimerization via a square scheme). Due to the equivalence of the two TTF

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

• may be warranted. Conclusion To better understand how PTFE tape functions as a semipermeable membrane, we examined its behavior and compared it to bulk PTFE. We included both simple diffusion processes and chemical reactions to examine the effects of solvents and reagents on the permeability of the

Photovoltaic-driven organic electrosynthesis and efforts toward more sustainable oxidation reactions

• Bichlien H. Nguyen,
• Robert J. Perkins,
• Jake A. Smith and
• Kevin D. Moeller

Beilstein J. Org. Chem. 2015, 11, 280–287, doi:10.3762/bjoc.11.32

• . Keywords: electrochemistry; sustainable oxidation reactions; visible light; Introduction Organic electrochemistry is an extremely versatile tool for conducting a wide variety of chemical reactions [1][2][3]. This versatility stems from both the gentle, acid/base neutral reaction conditions employed for

Properties of cationic monosubstituted tetraalkylammonium cyclodextrin derivatives – their stability, complexation ability in solution or when deposited on solid anionic surface

• Martin Popr,
• Sergey K. Filippov,
• Nikolai Matushkin,
• Juraj Dian and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2015, 11, 192–199, doi:10.3762/bjoc.11.20

• capillary zone electrophoresis [8][9][10][11][12] and also as catalysts of chemical reactions [13][14][15]. The main goal of our research is to explore the possibility of binding of the monosubstituted cationic CD derivatives to an anionic surface by simple electrostatic interactions. Such an assembly could

First chemoenzymatic stereodivergent synthesis of both enantiomers of promethazine and ethopropazine

• Paweł Borowiecki,
• Daniel Paprocki and
• Maciej Dranka

Beilstein J. Org. Chem. 2014, 10, 3038–3055, doi:10.3762/bjoc.10.322

• aim of this study was to take advantage of the extraordinary properties of enzyme catalysis and develop a new method based on lipase-mediated kinetic resolution (KR) of 1-(10H-phenothiazin-10-yl)propan-2-ol enantiomers, which combined with convenient chemical reactions could provide a simple and

Lateral ordering of PTCDA on the clean and the oxygen pre-covered Cu(100) surface investigated by scanning tunneling microscopy and low energy electron diffraction

• Stefan Gärtner,
• Benjamin Fiedler,
• Oliver Bauer,
• Antonela Marele and
• Moritz M. Sokolowski

Beilstein J. Org. Chem. 2014, 10, 2055–2064, doi:10.3762/bjoc.10.213

• this elevated temperatures the PTCDA molecules have undergone different kinds of chemical reactions. Therefore no intact desorption can be expected, in agreement with the TPD experiments of Schmidt et al. [8]. A non-dissociative adsorption on Cu(100) is further corroborated by STM images of PTCDA on

Synthesis of a bifunctional cytidine derivative and its conjugation to RNA for in vitro selection of a cytidine deaminase ribozyme

• Nico Rublack and
• Sabine Müller

Beilstein J. Org. Chem. 2014, 10, 1906–1913, doi:10.3762/bjoc.10.198

• from aptamers for simple binding of defined ligands, also RNAs for catalysis of chemical reactions have been selected. In the latter case, a key step often is the conjugation of one of the two reactants to the library, requiring suitable strategies for terminal or internal RNA functionalization. With

• peptide bond formation, artificial ribonucleic acids developed by in vitro selection have been shown to catalyze a wide variety of organic chemical reactions [3][4][5]. Moreover, several of these developed ribozymes promote reactions of metabolic relevance in modern life organisms. Impressive examples are

A complete series of 6-deoxy-monosubstituted tetraalkylammonium derivatives of α-, β-, and γ-cyclodextrin with 1, 2, and 3 permanent positive charges

• Martin Popr,
• Simona Hybelbauerová and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2014, 10, 1390–1396, doi:10.3762/bjoc.10.142

• excellent chiral selectors in capillary zone electrophoresis (CZE) [18][19] and as catalysts of chemical reactions [20][21]. The synthesis of some cationic derivatives of β-CD have already been described in the literature (namely 6I-(N,N,N-trimethylammonio)-6I-deoxy-β-cyclodextrin [21] and 6I-(N,N,N’,N‘,N

Automated solid-phase peptide synthesis to obtain therapeutic peptides

• Veronika Mäde,
• Sylvia Els-Heindl and
• Annette G. Beck-Sickinger

Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118

• solutions. The first liquid-handling apparatus performing SPPS of this type was described in 1965 [24]. The improvement of chemical reactions, solid supports, linkers and especially the development of the Fmoc-based SPPS-strategy [31][37] have contributed to simplification and many advancement of following

• ), the N-terminus of hPP was protected with Nvoc and after cleavage from resin, selective PEGylation was performed in solution followed by specific Nvoc removal [99]. Conclusion The production of peptides by automated synthesis on solid support provides a great variety of benefits. Chemical reactions

Site-selective covalent functionalization at interior carbon atoms and on the rim of circumtrindene, a C₃₆H₁₂ open geodesic polyarene

• Hee Yeon Cho,
• Ronald B. M. Ansems and
• Lawrence T. Scott

Beilstein J. Org. Chem. 2014, 10, 956–968, doi:10.3762/bjoc.10.94

• functionalization of circumtrindene Since the isolation and characterization of the first polycyclic aromatic hydrocarbons in the 1800s, a tremendous range of chemical reactions on such compounds has been developed [41][42]. Most of this chemistry involves chemical modifications on the edge carbons and has been

Tailoring of organic dyes with oxidoreductive compounds to obtain photocyclic radical generator systems exhibiting photocatalytic behavior

• Christian Ley,
• Julien Christmann,
• Ahmad Ibrahim,
• Luciano H. Di Stefano and
• Xavier Allonas

Beilstein J. Org. Chem. 2014, 10, 936–947, doi:10.3762/bjoc.10.92

• of the complex kinetics underlying PCIS chemical reactions, allowing a better and simplest selection of chemicals combination. Results and Discussion In order to outline this behavior, the photochemical consumption of the dye (i.e., photolysis) was studied in a typical Type II and a 3-cpt PCIS based

Synthesis of nucleotide–amino acid conjugates designed for photo-CIDNP experiments by a phosphotriester approach

• Tatyana V. Abramova,
• Olga B. Morozova,
• Vladimir N. Silnikov and
• Alexandra V. Yurkovskaya

Beilstein J. Org. Chem. 2013, 9, 2898–2909, doi:10.3762/bjoc.9.326

• spin hyperpolarization, which occurs in transient radical pairs on a microsecond time scale. Nuclear spin hyperpolarization is preserved in diamagnetic products of chemical reactions for several seconds allowing for NMR detection. This approach is based on the phenomenon of Chemically Induced Dynamic

Flow microreactor synthesis in organo-fluorine chemistry

• Hideki Amii,
• Aiichiro Nagaki and
• Jun-ichi Yoshida

Beilstein J. Org. Chem. 2013, 9, 2793–2802, doi:10.3762/bjoc.9.314

• faced with problems such as the difficulties in handling of fluorinating reagents and in controlling of chemical reactions. Recently, flow microreactor synthesis has emerged as a new methodology for producing chemical substances with high efficiency. This review outlines the successful examples of

• on the market contain fluorine atoms [6][9][10]. Despite increased demands in wide fields of science, synthesis of fluoro-organic compounds is still often faced with problems such as the difficulty in handling of fluorinating reagents and in controlling of chemical reactions. Furthermore, low

• increasingly popular method in organic chemistry [14][15][16][17]. Flow microreactor systems serve as an effective method for precise control of chemical reactions. Not only operational safety, but also extremely fast mixing, efficient heat transfer, and precise residence time control by virtue of the

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

• ][11][12][13][14][15][16][17]. In the past years, continuous-flow chemistry has received considerable attention and microstructured continuous-flow devices have emerged as useful devices for different chemical reactions [18][19][20][21][22]. Microreactor technology offers numerous practical advantages

One-pot sequential synthesis of isocyanates and urea derivatives via a microwave-assisted Staudinger–aza-Wittig reaction

• Diego Carnaroglio,
• Katia Martina,
• Giovanni Palmisano,
• Andrea Penoni,
• Claudia Domini and
• Giancarlo Cravotto

Beilstein J. Org. Chem. 2013, 9, 2378–2386, doi:10.3762/bjoc.9.274

• heat and mass transfer provided by dielectric heating and sonochemical conditions [24][25]. In general, MW in organic synthesis is a valid response to problems regarding long reaction times and a high reagent excess. The use of dielectric heating to promote chemical reactions has become well

The rapid generation of isothiocyanates in flow

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 1613–1619, doi:10.3762/bjoc.9.184

• Marcus Baumann Ian R. Baxendale Department of Chemistry, University of Durham, South Road, Durham DH1 3LE, United Kingdom 10.3762/bjoc.9.184 Abstract Isothiocyanates are versatile starting materials for a wide range of chemical reactions. However, their high nucleophilic susceptibility means they

Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production

• Sándor B. Ötvös,
• Ádám Georgiádes,
• István M. Mándity,
• Lóránd Kiss and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2013, 9, 1508–1516, doi:10.3762/bjoc.9.172

• ] and conventional batch experiments [76]. In conventional batch-based chemistry, the scale-up of chemical reactions can be a challenge because the output depends on the batch size. The situation becomes even more complicated when unstable reactants such as azides are handled on a large scale. However

Hypervalent iodine/TEMPO-mediated oxidation in flow systems: a fast and efficient protocol for alcohol oxidation

• Nida Ambreen,
• Ravi Kumar and
• Thomas Wirth

Beilstein J. Org. Chem. 2013, 9, 1437–1442, doi:10.3762/bjoc.9.162

• platforms to perform reactions under continuous flow rather than in batch mode has led to improvements regarding safety and sustainability. Microreactor technology can be beneficial over classical approaches in a variety of chemical reactions. Many reactions can benefit from the properties of microreactors

Copper-catalyzed aerobic aliphatic C–H oxygenation with hydroperoxides

• Pei Chui Too,
• Ya Lin Tnay and
• Shunsuke Chiba

Beilstein J. Org. Chem. 2013, 9, 1217–1225, doi:10.3762/bjoc.9.138

• radical; 1,5-H radical shift; hydroperoxides; molecular oxygen; Introduction Aliphatic sp3 C–H bonds are ubiquitous components in organic molecules but rather inert towards most of the chemical reactions. It thus remains as one of the most challenging topics in organic synthesis to develop catalytic

Camera-enabled techniques for organic synthesis

• Steven V. Ley,
• Richard J. Ingham,
• Matthew O’Brien and
• Duncan L. Browne

Beilstein J. Org. Chem. 2013, 9, 1051–1072, doi:10.3762/bjoc.9.118

• plurality of chemical reactions in an array format (Figure 17). This system is specifically targeted at oligonucleotide synthesis where multiple reactions may frequently be performed in parallel, and so this invention included the development of optical analysis software to process the vast amount of data