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Search for "hydrocarbon" in Full Text gives 187 result(s) in Beilstein Journal of Organic Chemistry.

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

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  • striking differences regarding their reaction with water. While BIFOP–Cl is nearly completely unreactive, its oxo-derivative O–BIFOP–Cl reacts instantly with water, yielding a tricyclic hydrocarbon unit after rearrangement. The analysis of the crystal structure of O–BIFOP–Cl and BIFOP–Cl revealed that the
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Published 04 Mar 2015

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

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  • double layer immediately around the electrode surface that can prevent molecules from reaching the electrode. For example, a “greasy” hydrocarbon-based electrolyte will form a hydrophobic double layer and exclude polar molecules from the region surrounding the electrode. This was the case when Et4NOTs
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Published 23 Feb 2015

Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin

  • Jun Terao,
  • Yohei Konoshima,
  • Akitoshi Matono,
  • Hiroshi Masai,
  • Tetsuaki Fujihara and
  • Yasushi Tsuji

Beilstein J. Org. Chem. 2014, 10, 2800–2808, doi:10.3762/bjoc.10.297

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  • Jun Terao Yohei Konoshima Akitoshi Matono Hiroshi Masai Tetsuaki Fujihara Yasushi Tsuji Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, Japan 10.3762/bjoc.10.297 Abstract We synthesized symmetrically insulated oligo(para
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Published 28 Nov 2014

Microsolvation and sp2-stereoinversion of monomeric α-(2,6-di-tert-butylphenyl)vinyllithium as measured by NMR

  • Rudolf Knorr,
  • Monika Knittl and
  • Eva C. Rossmann

Beilstein J. Org. Chem. 2014, 10, 2521–2530, doi:10.3762/bjoc.10.263

Graphical Abstract
  • -BuBr to yield hydrocarbon 7. In THF as the solvent, such a mixing problem was encountered already at −70 °C: During the cautious addition of n-BuLi to bromoalkene 3, 4 was generated and rapidly converted into 6, 7, and 8a despite the presence of residual n-BuLi. In consideration of these various
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Published 29 Oct 2014

Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation

  • Yiyang Liu,
  • Marc Liniger,
  • Ryan M. McFadden,
  • Jenny L. Roizen,
  • Jacquie Malette,
  • Corey M. Reeves,
  • Douglas C. Behenna,
  • Masaki Seto,
  • Jimin Kim,
  • Justin T. Mohr,
  • Scott C. Virgil and
  • Brian M. Stoltz

Beilstein J. Org. Chem. 2014, 10, 2501–2512, doi:10.3762/bjoc.10.261

Graphical Abstract
  • quaternary centers, two of which are stereogenic. Being a hydrocarbon, (−)-thujopsene (10) has few natural handles for retrosynthetic analysis. Inspired by the complexity of this relatively small natural product, several total syntheses of racemic 10 have been reported [25][26][27][28][29] along with at
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Published 28 Oct 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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  • functional groups weaken C–H bonds, yielding relatively stable radicals, in turn resulting in selective CO2 fixation [150]. Another patented system uses electrogenerated bases to deprotonate a weakly acidic hydrocarbon group forming anions which are carboxylated in the presence of CO2. Meanwhile, proton
  • reaction product. The base precursor should be more easily electroreduced than the weakly acidic hydrocarbon group and carbon dioxide, and should not undergo a nucleophilic attack by either the hydrocarbon anion or the electrogenerated base. Therefore, the base precursor should be sterically hindered at or
  • near the site(s) where reduction will occur. The electrogenerated base must be a strong enough Brønsted base to deprotonate the weakly acidic hydrocarbon group. Ethenetetracarboxylate tetraesters are typical base precursors, suited for the electrocarboxylation of N-alkyldiglycolimides (Scheme 22). This
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Published 27 Oct 2014

Building complex carbon skeletons with ethynyl[2.2]paracyclophanes

  • Ina Dix,
  • Lidija Bondarenko,
  • Peter G. Jones,
  • Thomas Oeser and
  • Henning Hopf

Beilstein J. Org. Chem. 2014, 10, 2013–2020, doi:10.3762/bjoc.10.209

Graphical Abstract
  • -diethynyl[2.2]paracyclophane, i.e., the hydrocarbon with two ethynyl groups in vicinal position in the same ring [2][3]. If, however, our target molecules are to have the two triple bonds in different benzene rings, the pseudo-gem-diethynyl[2.2]paracyclophane 2 is the analog of 1 (Scheme 1). Analogously
  • The oxidative dimerization (Glaser coupling) of the achiral hydrocarbon 2 took place effortlessly and in high yield (Scheme 3). However, we have been unable so far to determine the exact structure of the isolated dimer. As shown in Scheme 3, in principle, two different dimers of 2 could be formed: one
  • /propan-2-ol, 9:1) and [α]D25 = 43 ° (c 0.533, hexane/propan-2-ol, 9:1). The later eluting dimer is the “parallel” hydrocarbon 12 (Figure 2). This compound (Figure 2) crystallizes with imposed inversion symmetry (and is thus achiral), but the effective symmetry is C2h (2/m) with r.m.s.d. 0.14 Å. Compound
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Published 27 Aug 2014

Supercritical carbon dioxide: a solvent like no other

  • Jocelyn Peach and
  • Julian Eastoe

Beilstein J. Org. Chem. 2014, 10, 1878–1895, doi:10.3762/bjoc.10.196

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  • environmental hazards [64][65][66][67]. Investigations focusing on partially fluorinated hybrid surfactants as a way to reduce fluorine content began in 1994 with the design and synthesis of F7H7, a partially fluorinated surfactant with an n-C7 fluorocarbon chain and an n-C7 hydrocarbon chain (Table 1, compound
  • relationship between Φsurf, Ptrans and γcmc (surface tension of aqueous solutions) has been identified, with Φsurf increasing with decreased Ptrans and γcmc. This has been observed with a range of surfactants, including fully and partially fluorinated and hydrocarbon-based surfactants (Figure 2). Surfactant
  • tails – siloxane, hydrocarbon and oxygenated surfactants: Though the use of fluorocarbons can be significantly reduced through the development of hybrid, semi-fluorinated surfactants, the race toward the development of a non-fluorinated, CO2 soluble surfactant is of primary focus in this field. These
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Published 14 Aug 2014

Aryl substitution of pentacenes

  • Andreas R. Waterloo,
  • Anna-Chiara Sale,
  • Dan Lehnherr,
  • Frank Hampel and
  • Rik R. Tykwinski

Beilstein J. Org. Chem. 2014, 10, 1692–1705, doi:10.3762/bjoc.10.178

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  • ; pentacene; π-stacking; polycyclic aromatic hydrocarbon; solid-state structure; Introduction Conjugated organic molecules are promising candidates for use in optoelectronic applications including OLEDs [1], photovoltaics [2], and OFETs [3]. Even though there is literally an infinite number of possibilities
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Published 28 Jul 2014

Influence of perylenediimide–pyrene supramolecular interactions on the stability of DNA-based hybrids: Importance of electrostatic complementarity

  • Christian B. Winiger,
  • Simon M. Langenegger,
  • Oleg Khorev and
  • Robert Häner

Beilstein J. Org. Chem. 2014, 10, 1589–1595, doi:10.3762/bjoc.10.164

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  • sciences. They play a crucial role in the stacking of nucleobases, thus stabilising the DNA double helix. The following paper describes a series of chimeric DNA–polycyclic aromatic hydrocarbon (PAH) hybrids. The PAH building blocks are electron-rich pyrene and electron-poor perylenediimide (PDI), and were
  • molecular scaffold for arranging various types of chromophores [39][40][41][42][43][44]. Recently, we reported that oligoarenotides (oligomers with an alternating phosphodiester-aromatic hydrocarbon motif) exhibit similar structural properties as nucleic acids, and although the aromatic hydrocarbons cannot
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Published 11 Jul 2014

The search for new amphiphiles: synthesis of a modular, high-throughput library

  • George C. Feast,
  • Thomas Lepitre,
  • Xavier Mulet,
  • Charlotte E. Conn,
  • Oliver E. Hutt,
  • G. Paul Savage and
  • Calum J. Drummond

Beilstein J. Org. Chem. 2014, 10, 1578–1588, doi:10.3762/bjoc.10.163

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  • cycloaddition (CuAAC) reaction. The tails were synthesised from two core alkyne-tethered intermediates, which were subsequently functionalised with hydrocarbon chains varying in length and degree of unsaturation and branching, while the five sugar head groups were selected with ranging substitution patterns and
  • interfaces that curve towards the aqueous domain) are desirable as they maintain the same lyotropic structure upon dilution [8]. Inverse phases typically form from amphiphiles with multiple hydrocarbon-chain tails. Therefore, to tune our amphiphiles towards inverse phase formation, we undertook the synthesis
  • that enabled a late-stage, modular addition of the hydrocarbon chains; the products of which could be taken straight into the high-throughput CuAAC reaction. To this end, diol 2 was synthesised by esterification of commercially available 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoic acid (1), according
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Published 10 Jul 2014

Syntheses of fluorooxindole and 2-fluoro-2-arylacetic acid derivatives from diethyl 2-fluoromalonate ester

  • Antal Harsanyi,
  • Graham Sandford,
  • Dmitri S. Yufit and
  • Judith A.K. Howard

Beilstein J. Org. Chem. 2014, 10, 1213–1219, doi:10.3762/bjoc.10.119

Graphical Abstract
  • corresponding reactivity profiles [14]. However, it does not necessarily follow that reactions for which regio- and stereoselectivity profiles are well established for hydrocarbon systems will be similar to those for corresponding selectively fluorinated systems and, indeed, this is often not the case [15]. The
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Published 22 May 2014

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

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  • reactions and to probe the magnetic environment of the concave/convex space around the hydrocarbon bowl. For both classes of functionalization, computational results are reported to complement the experimental observations. Keywords: Bingel–Hirsch reaction; buckybowl; carbon nanomaterials; cyclopropanation
  • ; polycyclic aromatic hydrocarbon; Prato reaction; Introduction Investigations into the structures and properties of geodesic polyarenes began with the synthesis of corannulene (1, C20H10) in 1966 [1][2] and were greatly stimulated by the discovery of buckminsterfullerene (2, C60) in 1985 (Figure 1) [3
  • formation at an interior carbon atom, despite the long history of aromatic hydrocarbon chemistry [41][42]. These PAHs (1 and 10) are obviously nonplanar and have the same patterns of pentagons and hexagons as that found on the surface of fullerene C60. The distortions of the π-systems in these molecules
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Published 28 Apr 2014

Conformational analysis of 2,2-difluoroethylamine hydrochloride: double gauche effect

  • Josué M. Silla,
  • Claudimar J. Duarte,
  • Rodrigo A. Cormanich,
  • Roberto Rittner and
  • Matheus P. Freitas

Beilstein J. Org. Chem. 2014, 10, 877–882, doi:10.3762/bjoc.10.84

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  • -difluoroethylamine hydrochloride; gauche effect; hydrogen bonding; Introduction The conformational isomerism of alkylamines devotes interest because intramolecular effects relative to hydrocarbon analogues are affected by the electronegativity of the nitrogen atom and by the basicity of the amino group. However
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Published 16 Apr 2014

Metal and metal-free photocatalysts: mechanistic approach and application as photoinitiators of photopolymerization

  • Jacques Lalevée,
  • Sofia Telitel,
  • Pu Xiao,
  • Marc Lepeltier,
  • Frédéric Dumur,
  • Fabrice Morlet-Savary,
  • Didier Gigmes and
  • Jean-Pierre Fouassier

Beilstein J. Org. Chem. 2014, 10, 863–876, doi:10.3762/bjoc.10.83

Graphical Abstract
  • under a red laser line exposure at 635 nm. This result was very important as cationic polymerization in these irradiation conditions was not possible previously. Changing Vi or the anthracene derivative for a hydrocarbon (e.g. pyrene, naphthacene, pentacene) allows a tunable absorption of the system
  • from 400 nm to 650 nm: exposure of the hydrocarbon/Ph2I+/TTMSS system to soft purple (405 nm), blue (457, 462 or 473 nm), green (514, 532 nm), yellow (591 nm) or red (630, 635 nm) LED bulbs or laser diodes becomes successful. In rare examples, the PIC/methyldiethanolamine MDEA/phenacyl bromide R-Br
  • recently achieved in FRP for the first time [54][55]: they involve hydrocarbon derivatives (e.g., pyrene, naphtacene, pentacene), an amine (e.g., ethyl dimethylaminobenzoate) and an alkyl halide (e.g., phenacyl bromide); the mechanism is similar to that shown in Scheme 12. As above, a tunable absorption of
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Published 15 Apr 2014

Structure elucidation of female-specific volatiles released by the parasitoid wasp Trichogramma turkestanica (Hymenoptera: Trichogrammatidae)

  • Armin Tröger,
  • Teris A. van Beek,
  • Martinus E. Huigens,
  • Isabel M. M. S. Silva,
  • Maarten A. Posthumus and
  • Wittko Francke

Beilstein J. Org. Chem. 2014, 10, 767–773, doi:10.3762/bjoc.10.72

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  • identified as the hydrocarbon 2,6,8,12-tetramethyltrideca-2,4-diene (A) and the corresponding allylic alcohol 2,6,8,12-tetramethyltrideca-2,4-diene-1-ol (B) [12]. Since the two proposed structures were deduced from analytical data only, the aim of the present study was to scrutinize these suggestions by
  • unambiguous synthesis. Results and Discussion The 70 eV EI mass spectra of the two natural products A and B are depicted in Figure 1 [12]. Because the carbon skeleton had been reported to be the same in both compounds, we used the hydrocarbon A as the first target for the preparation of a reference sample. As
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Published 02 Apr 2014

Carbenoid-mediated nucleophilic “hydrolysis” of 2-(dichloromethylidene)-1,1,3,3-tetramethylindane with DMSO participation, affording access to one-sidedly overcrowded ketone and bromoalkene descendants§

  • Rudolf Knorr,
  • Thomas Menke,
  • Johannes Freudenreich and
  • Claudio Pires

Beilstein J. Org. Chem. 2014, 10, 307–315, doi:10.3762/bjoc.10.28

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  • ; DMSO; nucleophilic vinylic substitution; steric hindrance; Introduction The 1,1,3,3-tetramethylindan-2-yl(idene) fragments shown in the hydrocarbon parts of formulae 4–8 (Scheme 1) are preferable to the corresponding acyclic di-tert-butylmethylidene moiety (t-Bu2C in 1–3) as the shielding substituent
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Published 31 Jan 2014

The difluoromethylene (CF2) group in aliphatic chains: Synthesis and conformational preference of palmitic acids and nonadecane containing CF2 groups

  • Yi Wang,
  • Ricardo Callejo,
  • Alexandra M. Z. Slawin and
  • David O’Hagan

Beilstein J. Org. Chem. 2014, 10, 18–25, doi:10.3762/bjoc.10.4

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  • aliphatic chain. Specifically 8,8,10,10- and 8,8,11,11-tetrafluorohexadecanoic acids (6b and 6c) are prepared as well as the singly modified analogue 8,8-difluorohexadecanoic acid (6a). Also 8,8,11,11-tetrafluorononadecane (27) is prepared as a pure hydrocarbon containing a 1,4-di-CF2 motif. The modified
  • solid state. Thus it appeared appropriate to prepare a true hydrocarbon chain to further investigate the conformational preference of the 1,4-di-CF2 motif. Accordingly we selected to prepare tetrafluorononadecane 27. This is a long chain hydrocarbon with the 1,4-di-CF2 motif placed centrally. The
  • that this is the preferred conformation of this motif in a hydrocarbon chain. Conclusion In conclusion, we have synthesised three palmitic acid analogues 6a–c carrying regiospecifically located CF2 groups. The tetrafluorononadecane 27 was also prepared as an example of a true hydrocarbon. Relatively
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Published 06 Jan 2014

Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine

  • Holger Erdbrink,
  • Elisabeth K. Nyakatura,
  • Susanne Huhmann,
  • Ulla I. M. Gerling,
  • Dieter Lentz,
  • Beate Koksch and
  • Constantin Czekelius

Beilstein J. Org. Chem. 2013, 9, 2009–2014, doi:10.3762/bjoc.9.236

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  • acids (Ile or Val) are the most stabilizing amino acids in parallel packing arrangements, because they project the hydrocarbon side chain from the β-carbon atom directly into the helical interface, whereas perpendicular packing precludes β-branched residues from occupying these sites and Leu is favored
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Published 02 Oct 2013

Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements

  • Jungho Jun,
  • Hyu-Suk Yeom,
  • Jun-Hyun An and
  • Seunghoon Shin

Beilstein J. Org. Chem. 2013, 9, 1724–1729, doi:10.3762/bjoc.9.198

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  • = di-t-butyl-o-biphenylphosphine, JohnPhos) formed in situ was used as catalyst, the reaction was more efficient in chlorinated solvents rather than polar aprotic or aromatic hydrocarbon solvents (Table 1, entries 1–7). Contrary to the previous [4 + 2] cycloaddition, formal enyne cross metathesis or [2
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Published 22 Aug 2013

Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water

  • Daisuke Hirose and
  • Tsuyoshi Taniguchi

Beilstein J. Org. Chem. 2013, 9, 1713–1717, doi:10.3762/bjoc.9.196

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  • treatment of the crude product with di-tert-butyl dicarbonate (Boc2O) (Scheme 2). This experiment emphasised the potential of the present multifunctionalization method because the simple unsaturated hydrocarbon 1 can be converted into the highly polar amino-1,4-diol compound in only two steps. The plausible
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Published 20 Aug 2013

The preparation of several 1,2,3,4,5-functionalized cyclopentane derivatives

  • André S. Kelch,
  • Peter G. Jones,
  • Ina Dix and
  • Henning Hopf

Beilstein J. Org. Chem. 2013, 9, 1705–1712, doi:10.3762/bjoc.9.195

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  • that has all the carbon atoms of the final [5]radialene (3) already in place is 1,2,3,4,5-pentamethylcyclopenta-1,3-diene (8). Formally this hydrocarbon merely has to be dehydrogenated three times to provide the target molecule. To accomplish this goal we first had to replace these hydrogen atoms by a
  • to 32 is also summarized in Scheme 7. Since in all our bromination experiments we isolated small amounts of a hydrocarbon that, according to mass spectral analysis, has the formula C20H30, i.e. is a dimer of the starting material, we assume that the permethylcyclopentadienyl radical 33 plays an
  • 32) that could lead to [5]radialene (3) in hand, a synthesis of this long missing hydrocarbon is now within sight. Structure of 19 in the crystal; ellipsoids represent 50% probability levels. Structure of 24 in the crystal; ellipsoids represent 30% probability levels. Structure of 26 in the crystal
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Published 19 Aug 2013

Bromination of hydrocarbons with CBr4, initiated by light-emitting diode irradiation

  • Yuta Nishina,
  • Bunsho Ohtani and
  • Kotaro Kikushima

Beilstein J. Org. Chem. 2013, 9, 1663–1667, doi:10.3762/bjoc.9.190

Graphical Abstract
  • species for the bromination. The generation of CHBr3 was confirmed by NMR spectroscopy and GC–MS spectrometry analysis, indicating that the present bromination involves the homolytic cleavage of a C–Br bond in CBr4 followed by radical abstraction of a hydrogen atom from a hydrocarbon. Keywords
  • : bromination; free radical; hydrocarbon; light-emitting diode; photo irradiation; Introduction Bromination reactions of organic compounds are fundamental reactions for providing a wide variety of organic precursors for industrial materials [1][2][3][4][5][6][7][8]. Generally, the bromination of saturated
  • the second bromination was not assigned at this point. Conclusion In conclusion, we have developed a method for the hydrocarbon bromination induced by LED irradiation using CBr4 as a bromine source. The present reaction system did not require any additives, catalysts, heating, or inert conditions, and
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Published 14 Aug 2013

True and masked three-coordinate T-shaped platinum(II) intermediates

  • Manuel A. Ortuño,
  • Salvador Conejero and
  • Agustí Lledós

Beilstein J. Org. Chem. 2013, 9, 1352–1382, doi:10.3762/bjoc.9.153

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Published 09 Jul 2013

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

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  • saddle points by frequency calculations. The experimental kinetic and spectroscopic data was all obtained in the nonpolar hydrocarbon solvents t-BuPh or cyclopropane. Solvent effects, particularly differences in solvation between the neutral reactants and neutral transition states, were therefore
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Published 04 Jun 2013
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