European Journal of Organic Chemistry

Cover image for Vol. 2012 Issue 32

November 2012

Volume 2012, Issue 32

Pages 6299–6459

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Full Papers
    1. You have free access to this content
      Special Electronic Structure and Extended Supramolecular Oligomerization of Anionic 1,4-Dicorannulenylbenzene (Eur. J. Org. Chem. 32/2012)

      David Eisenberg, Jennifer M. Quimby, Derrick Ho, Ronit Lavi, Laurent Benisvy, Lawrence T. Scott and Roy Shenhar

      Article first published online: 26 OCT 2012 | DOI: 10.1002/ejoc.201290087

      Thumbnail image of graphical abstract

      The cover picture shows an artist's view of corannulene-based supramolecular polymers formed through the utilization of the charged polyarene stacking motif. When 1,4-dicorannulenylbenzene is reduced by lithium metal to an octaanion, it forms highly charged, supramolecular polymers based on the tendency of corannulene to form dimers that are held together by electrostatic interactions with multiple lithium cations. A strong effect of the benzene spacer on the electronic structure of the dianion, as well as on the average degree of polymerization, was revealed. Details are discussed in the article by Roy Shenhar et al. on p. 6321 ff. 3D modelling and design by Ewen Gilary, Designer and Creative Adviser (ewengilary@gmail.com)

  2. Graphical Abstract

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

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

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

      Immobilized Catalysts for Hydroformylation Reactions: A Versatile Tool for Aldehyde Synthesis (pages 6309–6320)

      Ângela C. B. Neves, Mário J. F. Calvete, Teresa M. V. D. Pinho e Melo and Mariette M. Pereira

      Article first published online: 18 SEP 2012 | DOI: 10.1002/ejoc.201200709

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      The most relevant results relating to the development and use of catalysts supported on mesoporous materials, hydrotalcite, carbon materials, and nanoparticles for metal-catalyzed hydroformylation of olefins reported over the last five years are reviewed. The results are analyzed with particular regard to reusability and leaching issues.

  5. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Full Papers
    1. Buckybowl Anions

      Special Electronic Structure and Extended Supramolecular Oligomerization of Anionic 1,4-Dicorannulenylbenzene (pages 6321–6327)

      David Eisenberg, Jennifer M. Quimby, Derrick Ho, Ronit Lavi, Laurent Benisvy, Lawrence T. Scott and Roy Shenhar

      Article first published online: 26 JUL 2012 | DOI: 10.1002/ejoc.201200714

      Thumbnail image of graphical abstract

      The reduction of 1,4-dicorannulenylbenzene is strongly affected by the benzene spacer, yielding an unexpected triplet ground state of the dianion and an octaanion that self-assembles into highly charged supramolecular oligomers that are longer than previously observed dicorannulenyl oligomers.

    2. Molecular Switches

      Synthesis and Photoisomerization of Rhodopsin-Based Molecular Switches (pages 6328–6334)

      Marina Blanco-Lomas, Pedro J. Campos and Diego Sampedro

      Article first published online: 28 SEP 2012 | DOI: 10.1002/ejoc.201200870

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      A family of photochemical switches inspired by a Rhodopsin chromophore is presented. The versatile synthetic route enables a variety of substituents to be included. The photophysical properties can be fine-tuned by changing the substituents within the structure.

    3. Laser Dyes

      Chlorinated BODIPYs: Surprisingly Efficient and Highly Photostable Laser Dyes (pages 6335–6350)

      Gonzalo Duran-Sampedro, Antonia R. Agarrabeitia, Inmaculada Garcia-Moreno, Angel Costela, Jorge Bañuelos, Teresa Arbeloa, Iñigo López Arbeloa, Jose Luis Chiara and María J. Ortiz

      Article first published online: 4 OCT 2012 | DOI: 10.1002/ejoc.201200946

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      Chlorination is a direct and low-cost strategy allowing significant enhancement of the optical properties of BODIPY dyes, overcoming some of their most important shortcomings for laser applications such as low absorptions at standard laser pumping wavelengths and/or low photostabilities.

    4. Supramolecular Chemistry

      [n]Pseudorotaxanes (n = 2, 3) from Self-Assembly of Two Cryptands and a 1,2-Bis(4-pyridinium)ethane Derivative (pages 6351–6356)

      Xuzhou Yan, Xiaodong Chi, Peifa Wei, Mingming Zhang and Feihe Huang

      Article first published online: 26 SEP 2012 | DOI: 10.1002/ejoc.201200964

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      Host–guest complexation and self-assembled structures formed between two crown ether-based cryptands and a 1,2-bis(4-pyridinium)ethane derivative are reported. A [3]pseudorotaxane forms from a dibenzo-24-crown-8-based cryptand and the 1,2-bis(4-pyridinium)ethane derivative, whereas a [2]pseudorotaxane is obtained from a bis(m-phenylene)-32-crown-10-based cryptand and the same guest.

    5. Diaryltrisphaeridine Derivatives

      Diaryltrisphaeridine Derivatives: Synthesis, Experimental Electrochemical and Photophysical Properties, and Theoretical Studies (pages 6357–6363)

      Alegría Caballero, Pedro J. Campos and Miguel A. Rodríguez

      Article first published online: 27 SEP 2012 | DOI: 10.1002/ejoc.201201051

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      The properties of diaryltrisphaeridines depend on the aryl substituents. In particular, dimethylamino groups induce a bright-green emission, which makes this a promising compound for use in fluorescence devices and molecular sensors. The green emission disappears on addition of HCl and this material can therefore also be used as a proton sensor. The results are rationalized by theoretical studies.

    6. Chiral Pool

      Derivatives of (–)-Isosteviol with Expanded Ring D and Various Oxygen Functionalities (pages 6364–6371)

      Christina Lohoelter, Dieter Schollmeyer and Siegfried R. Waldvogel

      Article first published online: 26 SEP 2012 | DOI: 10.1002/ejoc.201200970

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      Ring D of (–)-isosteviol was expanded to a variety of cyclohexanone derivatives wherein the carbonyl group can be located on all three potential positions. Since the starting material is readily available, new ex-chiral-pool building blocks are accessible.

    7. Cycloaddition Reactions

      Cycloaddition Reactions of Propiolamidinium Salts (pages 6372–6382)

      Werner Weingärtner and Gerhard Maas

      Article first published online: 28 SEP 2012 | DOI: 10.1002/ejoc.201201005

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      Acetylenes bearing single carboxamidinium groups have not previously been studied as cycloaddition partners. Here we report that thermally induced cycloadditions across their electron-deficient C≡C triple bonds can be achieved with nitrones, azides, and cyclopentadiene.

    8. Enzyme Models

      Synthesis of Tin-Containing Cyclodextrins as Potential Enzyme Models (pages 6383–6389)

      You Zhou, Lavinia Marinescu, Christian Marcus Pedersen and Mikael Bols

      Article first published online: 5 OCT 2012 | DOI: 10.1002/ejoc.201200756

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      Although modified tin hydrides are difficult to make, they are incredibly useful promoters of radical reactions. In this paper we report the first synthesis of a organotinchloride covalently bound to a cyclodextrin as a potential enzyme model.

    9. Organocatalysis

      Synthesis and Characterization of Monosaccharide Derivatives and Application of Sugar-Based Prolinamides in Asymmetric Synthesis (pages 6390–6406)

      Jyoti Agarwal and Rama Krishna Peddinti

      Article first published online: 4 OCT 2012 | DOI: 10.1002/ejoc.201200522

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      The catalytic activity of novel sugar-based prolinamide organocatalysts, obtained from the corresponding primary amines, was demonstrated in the asymmetric aldol reaction. The prolinamide 3a was established as efficient and powerful organocatalyst for the enantioselective aldol reaction between various cyclic/acyclic ketones and aromatic aldehydes through a mild and facile method under solvent-free conditions, and the aldol adducts were obtained in high levels of diastereo- and enantioselectivities.

    10. L-Proline-Catalyzed Activation of Methyl Ketones or Active Methylene Compounds and DMF-DMA for Syntheses of (2E)-3-Dimethylamino-2- propen-1-ones (pages 6407–6413)

      Dinesh Kumar, Damodara N. Kommi, Pradeep Chopra, Md Imam Ansari and Asit K. Chakraborti

      Article first published online: 4 OCT 2012 | DOI: 10.1002/ejoc.201200778

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      A covalent and noncovalent synchronously ambiphilic activation of methyl ketones or active methylene compounds with DMF-DMA (N,N-dimethylformamide dimethyl acetal) by L-proline for the syntheses of (2E)-3-dimethylamino-2-propen-1-ones is described.

    11. Organocatalyzed Intramolecular Michael Addition of Morita–Baylis–Hillman Adducts of β-Arylnitroethylenes: An Entry to 3-Aryl-4-nitrocyclohexanones (pages 6414–6419)

      Chada Raji Reddy, Motatipally Damoder Reddy and Kothapalli Haribabu

      Article first published online: 26 SEP 2012 | DOI: 10.1002/ejoc.201200884

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      Morita–Baylis–Hillman (MBH) adducts of β-arylnitroethylenes have been successfully converted into 3-aryl-4-nitrocyclohexanones through an organocatalyzed diastereoselective intramolecular Michael addition. The application of the method towards (±)-epibatidine and its analogues has also been achieved.

    12. Aza-C-Glycosides

      The Development of an Aza-C-Glycoside Library Based on a Tandem Staudinger/Aza-Wittig/Ugi Three-Component Reaction (pages 6420–6454)

      Tom Wennekes, Kimberly M. Bonger, Katrin Vogel, Richard J. B. H. N. van den Berg, Anneke Strijland, Wilma E. Donker-Koopman, Johannes M. F. G. Aerts, Gijsbert A. van der Marel and Herman S. Overkleeft

      Article first published online: 4 OCT 2012 | DOI: 10.1002/ejoc.201200923

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      We report the synthesis of a 64-member compound library of aza-C-glycosides starting from four carbohydrate-derived azido aldehydes by using the Staudinger/aza-Wittig/Ugi three-component reaction. A preliminary biological evaluation of the compound library as inhibitors of human acid glucosylceramidase is also reported.

    13. Isomerization

      Lewis Acid Promoted Double Bond Isomerization of Tetrahydroxanthones (pages 6455–6459)

      Anna M. Linsenmeier and Stefan Bräse

      Article first published online: 28 SEP 2012 | DOI: 10.1002/ejoc.201201009

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      Tetrahydroxanthones, readily available from salicylaldehydes and cycloalkenones, undergo isomerization upon treatment with AlCl3. Follow-up chemistry such as asymmetric Corey–Bakshi–Shibata (CBS) reduction provides highly functionalized tetrahydroxanthones.

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