Extrusion – back to the future: Using an established technique to reform automated chemical synthesis

• Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 65–75, doi:10.3762/bjoc.13.9

• of the mixture [39][40][41][42]. These materials are receiving a lot of attention due to their potential applications in metal deposition and as green media in chemical reactions [43]. James et al. have reported the preparation of DESs Reline 200 (choline chloride:urea, 1:2), choline chloride:zinc

Facile synthesis of a 3-deazaadenosine phosphoramidite for RNA solid-phase synthesis

• Elisabeth Mairhofer,
• Elisabeth Fuchs and
• Ronald Micura

Beilstein J. Org. Chem. 2016, 12, 2556–2562, doi:10.3762/bjoc.12.250

• nucleobases can be significantly shifted within a well-structured RNA fold [12][13][14][15]. To address RNA phenomena of that kind, comparative atomic mutagenesis is an indispensable means, and with respect to ribozymes, can deliver important insights into the RNA catalyzed chemical reactions and underlying

Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis

• Florin Albota,
• Mino R. Caira,
• Constantin Draghici,
• Florea Dumitrascu and
• Denisa E. Dumitrescu

Beilstein J. Org. Chem. 2016, 12, 2503–2510, doi:10.3762/bjoc.12.245

• interesting chemical reactions of sydnones are their electrophilic substitution at C-4 and their participation in 1,3-dipolar cycloaddition reactions with olefinic and acetylenic dipolarophiles to form pyrazoles and functional transformation at C-4 [20][21][22][23][24][25][26]. Herein we present the synthesis

A new paradigm for designing ring construction strategies for green organic synthesis: implications for the discovery of multicomponent reactions to build molecules containing a single ring

• John Andraos

Beilstein J. Org. Chem. 2016, 12, 2420–2442, doi:10.3762/bjoc.12.236

• “intrinsic greenness”, were critical in influencing whether or not chemical reactions could achieve a minimum standard of overall greenness, regardless of how much auxiliary material (solvents, etc.) was used. Optimization toward overall greenness was best achieved by first maximizing atom economy and

Robust C–C bonded porous networks with chemically designed functionalities for improved CO₂ capture from flue gas

• Damien Thirion,
• Joo S. Lee,
• Ercan Özdemir and
• Cafer T. Yavuz

Beilstein J. Org. Chem. 2016, 12, 2274–2279, doi:10.3762/bjoc.12.220

• as nitrogen in imine, Tröger’s base or azo linked networks [8][9][10][11], have led to materials with remarkable gas uptake properties. Compared to C–C bonded networks, C–O or C–N linked structures are less thermally stable or chemically resistant. Furthermore, the chemical reactions involved in the

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

• and instruments All reagents for performing the chemical reactions were used as received. CH2Cl2 for fluorescence measurements was purchased from Merck. Dimethylformamide for cyclic voltammetry measurements was purchased from Sigma-Aldrich and kept over molecular sieves. Column chromatography was

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

• impacted the art of organic synthesis and manufacture [1][2][3][4][5][6][7]. The efficiency of chemical reactions can be greatly enhanced over common batch processes and new approaches to the optimization of established reaction protocols and the execution of hitherto unfeasible processes can be enabled

• ][9][11][12]. Over the past decade, various reactor types and technical specifications have been developed to address the intricate challenges of many chemical reactions, including the handling of hazardous [13][14] or explosive [15][16] reagents, advanced concentration and temperature gradients [17

• selective oxidations of various organic molecules (Scheme 5). From a conceptual point of view, the combination of two of the most abundant “reagents” on the surface of our planet, oxygen and visible light, with a safe, scalable, and efficient reactor technology for chemical reactions constitutes an approach

TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

• Mei-Yuan Hsu,
• Yi-Pei Liu,
• Sarah Lam,
• Su-Ching Lin and
• Cheng-Chung Wang

Beilstein J. Org. Chem. 2016, 12, 1758–1764, doi:10.3762/bjoc.12.164

• the aforementioned methods. Furthermore, organic solvents in laboratories are associated with numerous health hazards [64], and most of them are consumed during chemical reactions, work-up and purification procedures. Especially, dichloromethane, one of the most general solvents for glycosylation

Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides

• Andrew W. Truman

Beilstein J. Org. Chem. 2016, 12, 1250–1268, doi:10.3762/bjoc.12.120

• amount of RiPP chemical diversity is generated from cyclisation reactions, and the current mechanistic understanding of these reactions will be discussed here. These cyclisations involve a diverse array of chemical reactions, including 1,4-nucleophilic additions, [4 + 2] cycloadditions, ATP-dependent

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