European Journal of Organic Chemistry

Cover image for Vol. 2015 Issue 4

February 2015

Volume 2015, Issue 4

Pages 663–891

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
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      Pentaerythritol-Based Energetic Materials Related to PETN (Eur. J. Org. Chem. 4/2015)

      Quirin J. Axthammer, Burkhard Krumm and Thomas M. Klapötke

      Article first published online: 21 JAN 2015 | DOI: 10.1002/ejoc.201590006

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      The cover picture shows a pentaerythritol tetracarbamate (PETNC) molecule, a new high explosive, which has a positive oxygen balance, is stable up to 196 °C and could be initiated with a standard detonator. PETNC is much less sensitive than pentaerythritol tetranitrate (PETN) or nitroglycerin but once detonated delivers the same lethal energy to the target. Moreover, due to its positive oxygen balance, it can also be used as a “green” oxidizer in pyrotechnical formulations. Details are discussed in the article by Thomas M. Klapötke et al. on 723 ff.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
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    1. Graphical Abstract: Eur. J. Org. Chem. 4/2015 (pages 663–669)

      Article first published online: 21 JAN 2015 | DOI: 10.1002/ejoc.201590008

  3. News

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
  4. Microreview

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Enantioenriched Organophosphorus Compounds

      Organocatalytic Synthesis of Optically Active Organophosphorus Compounds (pages 677–702)

      Marek Dzięgielewski, Jakub Pięta, Elżbieta Kamińska and Łukasz Albrecht

      Article first published online: 5 DEC 2014 | DOI: 10.1002/ejoc.201403184

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      Organophosphorus reagents play pivotal roles in modern organic synthesis and have found many applications for the preparation both of synthetically important compounds and of biologically relevant ones. They are now widely employed in asymmetric organocatalysis to afford optically active organophosphorus compounds. This review summarizes recent progress in this field of enantioselective synthesis.

  5. Short Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
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    1. Sensor for Cadmium Ions

      Synthesis of a Phenazine-Based 1,2,3-Triazole from Naturally Occurring Naphthoquinone Designed as a Probe for Cd2+ Ions (pages 703–709)

      Guilherme A. M. Jardim, Hállen D. R. Calado, Luiz A. Cury and Eufrânio N. da Silva Júnior

      Article first published online: 23 DEC 2014 | DOI: 10.1002/ejoc.201403011

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      In this study, the synthesis of a phenazine luminescent probe obtained from the natural product lapachol is described. The compound is modified through click chemistry to generate a binding site for Cd2+ ions. Photophysics and fluorescence studies are conducted to prove the efficiency of this sensor.

    2. Organocatalysis

      Divergent Phosphine-Catalyzed [2+4] or [3+2] Cycloaddition Reactions of γ-Substituted Allenoates with Oxadienes (pages 710–714)

      Erqing Li, Meijia Chang, Ling Liang and You Huang

      Article first published online: 22 DEC 2014 | DOI: 10.1002/ejoc.201403369

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      Dihydropyran and multifunctional cyclopentene derivatives are constructed from the same starting materials by using different phosphine catalysts. By controlling the nucleophilicity of the phosphine catalysts, the γ-substituted allenoates can selectively act as C3 or C2 synthons. The results suggest that the ethyl group of the γ-substituted allenoates plays a key role in the domino reaction.

    3. Cross-Dehydrogenative Coupling

      Palladium-Catalyzed α-Selective Alkenylation of Imidazo[1,2-a]pyridines through Aerobic Cross-Dehydrogenative Coupling Reaction (pages 715–718)

      Monoranjan Ghosh, Aswini Naskar, Shubhanjan Mitra and Alakananda Hajra

      Article first published online: 22 DEC 2014 | DOI: 10.1002/ejoc.201403372

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      The palladium-catalyzed highly regioselective vinylation of imidazopyridines through a cross-dehydrogenative coupling reaction is explored. The reaction proceeds with the aid of molecular oxygen as the sole oxidant. A series of branched α-vinylated products are obtained with high efficiency.

    4. Cycloisomerization

      Rhodium(I)-Catalyzed Cycloisomerization of Allene–Allenylcyclopropanes (pages 719–722)

      Takamasa Kawamura, Yasuaki Kawaguchi, Katsuya Sugikubo, Fuyuhiko Inagaki and Chisato Mukai

      Article first published online: 22 DEC 2014 | DOI: 10.1002/ejoc.201403535

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      The RhI-catalyzed intramolecular [5+2–2]-type cycloisomerization of allene–allenylcyclopropanes is developed. In this reaction, ethylene is liberated from the cyclopropane ring to afford the 1,5,6,7-tetrahydroazulene skeletons.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Energetic Materials

      Pentaerythritol-Based Energetic Materials Related to PETN (pages 723–729)

      Quirin J. Axthammer, Burkhard Krumm and Thomas M. Klapötke

      Article first published online: 25 NOV 2014 | DOI: 10.1002/ejoc.201403265

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      New tetravalent pentaerythritol tetranitrocarbamate (PETNC) and its tetraammonium salt have been synthesized by an efficient two-step synthesis starting from pentaerythritol, the precursor to pentaerythritol tetranitrate (PETN). Their energetic properties are discussed in comparison with PETN.

    2. Dehalogenation of Diiodoalkenes

      Mechanism and Scope of the Base-Induced Dehalogenation of (E)-Diiodoalkenes (pages 730–737)

      Daniel Resch, Chang Heon Lee, Siew Yoong Tan, Liang Luo and Nancy S. Goroff

      Article first published online: 15 DEC 2014 | DOI: 10.1002/ejoc.201402992

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      A diiodoalkene diester undergoes hydrolysis on treatment with KOH, but eliminates iodine on reaction with iodide salts. This orthogonal reactivity is just one example of the interesting chemistry that arises from the reactions of diiodoalkenes with Lewis bases. The mechanism for this mild reaction has been studied experimentally.

    3. Conformation Analysis

      Triphenylacetic Acid Amides: Molecular Propellers with Induced Chirality (pages 738–749)

      Natalia Prusinowska, Wioletta Bendzińska-Berus, Maciej Jelecki, Urszula Rychlewska and Marcin Kwit

      Article first published online: 16 DEC 2014 | DOI: 10.1002/ejoc.201403182

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      Weak but cooperative intramolecular interactions, either CH···O hydrogen bonds or local CH/CO dipole/dipole interactions, play a key role in the process of spectacular chirality transfer in triphenylacetamides.

    4. Aryne–Enol Ether Cycloadditions

      Cycloaddition of Arynes and Cyclic Enol Ethers as a Platform for Access to Stereochemically Defined 1,2-Disubstituted Benzocyclobutenes (pages 750–764)

      Vijayendar R. Yedulla, Padmanava Pradhan, Lijia Yang and Mahesh K. Lakshman

      Article first published online: 22 DEC 2014 | DOI: 10.1002/ejoc.201403250

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      Arynes undergo facile cycloaddition with cyclic enol ethers, through which [2+2] cycloaddition products were obtained from 2,3-dihydrofuran, 2,3-dihydro-3H-pyran, and 1,4-dioxene derivatives. Each product contains a cis ring fusion, utilizable for the synthesis of advanced benzocyclobutenes. The synthetic methodology is complemented by molecular modeling and detailed structural evaluations.

    5. Chirality

      Inherently Chiral Calix[5]arenes Incorporating an Axially Chiral Binaphthyl Moiety: Synthesis, Structures and Chiral Recognition (pages 765–774)

      Wen-Zhen Zhang, Ke Yang, Si-Zhe Li, Hui Ma, Jun Luo, Kai-Ping Wang and Wen-Sheng Chung

      Article first published online: 12 DEC 2014 | DOI: 10.1002/ejoc.201403298

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      Regioselective monoalkylation of 1,3-calix[5]crown-6 incorporating an axially chiral BINOL moiety produced readily separable, inherently chiral diastereomers.

    6. Isoindole Synthesis

      Synthesis of Isoindoles by One-Electron Reductions of Dibenzo[1,4]diazocines (pages 775–785)

      Marcel Bovenkerk and Birgit Esser

      Article first published online: 16 DEC 2014 | DOI: 10.1002/ejoc.201403315

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      A protocol for the synthesis of isoindoles through one-electron reductions of dibenzo[1,4]diazocines is reported. Six novel isoindole derivatives have been synthesized, and the reaction mechanism has been studied by 1H NMR spectroscopy and quantum chemical calculations.

    7. Helical Structures

      Through the Maze: Cross-Coupling Pathways to a Helical Hexaphenyl “Geländer” Molecule (pages 786–801)

      Michel Rickhaus, Linda Maria Bannwart, Oliver Unke, Heiko Gsellinger, Daniel Häussinger and Marcel Mayor

      Article first published online: 18 DEC 2014 | DOI: 10.1002/ejoc.201403322

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      The synthesis of a helical, interlinked Geländer (banister) type hexaphenyl oligomer is symbolized in the figure as a maze; this is a representation of both the often convoluted synthetic possibilities as well as the successful resolution of the maze to reach the target structure.

    8. Radical Reactions

      A Mild Radical Method for the Dimerzation of Dithiocarbamates (pages 802–809)

      Ning Chen, Xin Zhong, Pingfan Li and Jiaxi Xu

      Article first published online: 18 DEC 2014 | DOI: 10.1002/ejoc.201403348

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      A general, practical, and efficient method for the dimerization of dithiocarbamates has been developed that can be used to prepare the corresponding bis(1-arylimino-1-alkyl/arylthiomethyl) disulfides with dilauroyl peroxide as oxidant.

    9. Ruthenium Nanocatalysts

      Synthesis of Chiral Functionalised Cyclobutylpyrrolidines and Cyclobutylamino Alcohols from (–)-(S)-Verbenone – Applications in the Stabilisation of Ruthenium Nanocatalysts (pages 810–819)

      Jordi Aguilera, Isabelle Favier, Marta Sans, Àlex Mor, Ángel Álvarez-Larena, Ona Illa, Montserrat Gómez and Rosa M. Ortuño

      Article first published online: 16 DEC 2014 | DOI: 10.1002/ejoc.201403176

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      Pyrrolidines and amino alcohols anchored to chiral polysubstituted cyclobutane moieties are synthesised stereoselectively from (–)-verbenone. Some of them are appropriate stabilisers of ruthenium nanoparticles and find catalytic applications in the hydrogenation of arenes and nitrobenzene derivatives to afford selectively the corresponding cyclohexane or aniline derivatives.

    10. Donor–Acceptor Systems

      Tuning the Isomeric Fused Heteroaromatic Core of Small Donor–Acceptor Molecules to Alter Their Crystalline Nature and Enhance Photovoltaic Performance (pages 820–827)

      Dongfeng Dang, Manjun Xiao, Pei Zhou, Juan Zhong, Jiang Fan, Ning Su, Wenjing Xiong, Chuncheng Yang, Qiong Wang, Yafei Wang, Yong Pei, Renqiang Yang and Weiguo Zhu

      Article first published online: 22 DEC 2014 | DOI: 10.1002/ejoc.201403350

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      Two novel donor–acceptor (D–A) molecules of endo- and exo-DBST(BT-Cz)2 were synthesized with two benzothiadiazole-carbazole (BT-Cz) arms and an isomeric dibenzosexithiophene (DBST) core. Compared with the endo compound, exo-DBST(BT-Cz)2 exhibits an increased hole mobility of 1.1 × 10–4 cm2 V–1 s–1 and enhanced photovoltaic properties, with a PCE value of 2.13 % and FF of 0.61 in OSCs.

    11. Amination of Flavones

      Buchwald–Hartwig Reactions of Monohaloflavones (pages 828–839)

      Krisztina Kónya, Dávid Pajtás, Attila Kiss-Szikszai and Tamás Patonay

      Article first published online: 16 DEC 2014 | DOI: 10.1002/ejoc.201403108

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      A new and efficient approach to (substituted) aminoflavones and hybrids of flavones and amino acids using Buchwald–Hartwig coupling was developed and optimised.

    12. Synthetic Methods

      Stereoselective TiCl4-Mediated Aldol Reactions Starting from Acylsilanes (pages 840–846)

      Gangababu Marri, J. Satyanarayana Reddy, Johal Ruiz, Saibal Das and René Grée

      Article first published online: 16 DEC 2014 | DOI: 10.1002/ejoc.201403263

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      A new, simple and efficient method has been developed for the preparation of β-hydroxyacylsilanes through a Lewis acid mediated aldol condensation. The use of TiCl4 under optimized reaction conditions allows the preparation of the target molecules in fair-to-good yields with excellent syn selectivities.

    13. Natural Products

      Spirangien Derivatives from the Myxobacterium Sorangium cellulosum: Isolation, Structure Elucidation, and Biological Activity (pages 847–857)

      Nicole Bruns, Wera Collisi, Steffen Bernecker, Marc Stadler, Christian Richter, Harald Schwalbe and Markus Kalesse

      Article first published online: 16 DEC 2014 | DOI: 10.1002/ejoc.201403353

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      Eleven new spirangien derivatives have been isolated from the myxobacterium Sorangium cellulosum. The structures were elucidated by MS and various NMR methods. We used Murata's method and statistical analysis of the PKS gene cluster based on profile hidden Markov models to determine their configurations. All the spirangien derivatives showed high cytotoxicities against two cancer cell lines.

    14. Spirocyclic Dihydrofurans

      Diastereoselective Synthesis of Spirocyclic Dihydrofurans and 1-Oxaspiro[4.5]decan-6-one Derivatives from Norbornyl α-Diketones (pages 858–870)

      Surendra H. Mahadevegowda and Faiz Ahmed Khan

      Article first published online: 18 DEC 2014 | DOI: 10.1002/ejoc.201403087

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      A diastereoselective propargylation of non-enolizable norbornyl α-diketones and an efficient AgI-catalyzed cycloisomerization of the resulting α-keto homopropargyl alcohols bearing terminal alkynes leading to spirocyclic dihydrofurans have been reported. This methodology has been successfully used to synthesize 1-oxaspiro[4.5]decan-6-ones through acid-mediated Grob-type fragmentation reactions.

    15. Difluorinated Enol Ethers

      Modified Julia Olefination on Sugar-Derived Lactones: Synthesis of Difluoro-exo-glycals (pages 871–875)

      Samuel Habib and David Gueyrard

      Article first published online: 22 DEC 2014 | DOI: 10.1002/ejoc.201403175

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      We report the preparation of difluoro-exo-glycals by olefination of sugar-derived lactones using a modified Julia reaction.

    16. C–C Bond Formation

      Copper(II)-Promoted C–C Bond Formation by Oxidative Coupling of Two C(sp3)–H Bonds Adjacent to Carbonyl Group to Construct 1,4-Diketones and Tetrasubstituted Furans (pages 876–885)

      Shuai Mao, Ya-Ru Gao, Shao-Liang Zhang, Dong-Dong Guo and Yong-Qiang Wang

      Article first published online: 18 DEC 2014 | DOI: 10.1002/ejoc.201403274

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      Coupling of two C–H bonds adjacent to a carbonyl group: The copper(II)-promoted coupling of two C(sp3)–H bonds that are adjacent to a carbonyl group was carried out for the preparation of 2,3-disubstituted 1,4-diketones and tetrasubstituted furans. This economic approach features a wide substrate scope and a high functional group tolerance.

    17. Fluorinated Pyrazoles

      Multigram Synthesis of Fluoroalkyl-Substituted Pyrazole-4-carboxylic Acids (pages 886–891)

      Rustam T. Iminov, Alexander V. Mashkov, Ivan I. Vyzir, Bohdan A. Chalyk, Anton V. Tverdokhlebov, Pavel K. Mykhailiuk, Ludmila N. Babichenko, Andrey A. Tolmachev, Yulian M. Volovenko, Angelina Biitseva, Oleg V. Shishkin and Svetlana V. Shishkina

      Article first published online: 22 DEC 2014 | DOI: 10.1002/ejoc.201403295

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      Fluorinated pyrazolecarboxylic acids ― potential building blocks for agrochemical applications ― have been prepared on a multigram scale. The easy separation of the isomeric mixture of esters was the key feature of the synthesis.

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