Angewandte Chemie International Edition

Cover image for Vol. 47 Issue 28

June 27, 2008

Volume 47, Issue 28

Pages 5095–5259

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlight
    8. Reviews
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    1. Cover Picture: A Complete Catalytic Cycle for Supramolecular Methanol-to-Olefins Conversion by Linking Theory with Experiment (Angew. Chem. Int. Ed. 28/2008) (page 5095)

      David M. McCann, David Lesthaeghe, Philip W. Kletnieks, Darryl R. Guenther, Miranda J. Hayman, Veronique Van Speybroeck, Michel Waroquier and James F. Haw

      Article first published online: 23 JUN 2008 | DOI: 10.1002/anie.200890132

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      A complete catalytic cycle … for the conversion of methanol into olefins (MTO) in zeolite HZSM-5 is presented by J. F. Haw et al. in their Communication on page 5179 ff. The cycle is fully consistent with theoretical and experimental observations, and can be compared to a cycling race, with stages leading up to a finish that coincides with the starting point. For each stage, specific reaction barriers need to be overcome, as in the mountain stages of the Tour de France which separate the wheat from the chaff.

  2. Inside Cover

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    1. Inside Cover: “Conformational” Solvatochromism: Spatial Discrimination of Nonpolar Solvents by Using a Supramolecular Box of a π-Conjugated Zinc Bisporphyrin Rotamer (Angew. Chem. Int. Ed. 28/2008) (page 5096)

      Junko Aimi, Yuka Nagamine, Akihiko Tsuda, Atsuya Muranaka, Masanobu Uchiyama and Takuzo Aida

      Article first published online: 23 JUN 2008 | DOI: 10.1002/anie.200890133

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      Conformational solvatochromism has been used to discriminate nonpolar solvents by using a self-assembled chromophoric molecule. A. Tsuda, T. Aida, and co-workers describe in their Communication on page 5153 ff. the self-assembly of a bis(zinc pyridylporphyrin) rotamer with a π-conjugated linker to give a mixture of supramolecular boxes composed of planar and perpendicular conformers. The ratio of the two boxes changes depending on the solvent, and leads to a solvatochromic response.

  3. Graphical Abstract

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    1. Graphical Abstract: Angew. Chem. Int. Ed. 28/2008 (pages 5099–5108)

      Article first published online: 23 JUN 2008 | DOI: 10.1002/anie.200890134

  4. News

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    4. Graphical Abstract
    5. News
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    7. Highlight
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  5. Book Review

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    4. Graphical Abstract
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    7. Highlight
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  6. Highlight

    1. Top of page
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    1. Discovering Chemical Terra Incognita: Unusual Metallacycles and Their Reactions (pages 5118–5121)

      Uwe Rosenthal

      Article first published online: 3 JUN 2008 | DOI: 10.1002/anie.200801571

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      In the loop: Highly strained five-membered metallacycles, until very recently uncharted territory, are currently receiving much attention in organometallic chemistry. Recent publications are discussed in which the theoretically predicted 1-metallacyclopenta-2,3-dienes A are attained, filling the gap between 1-metallacyclopent-3-enes B and 1-metallacyclopenta-2,3,4-trienes C.

  7. Reviews

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    1. Chemical Design of Nanoparticle Probes for High-Performance Magnetic Resonance Imaging (pages 5122–5135)

      Young-wook Jun, Jae-Hyun Lee and Jinwoo Cheon

      Article first published online: 23 JUN 2008 | DOI: 10.1002/anie.200701674

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      Tailor made: Owing to their unique magnetic properties and being a size comparable to biological functional units, tailored magnetic nanoparticles (MNPs) are increasingly used as medical probes. Their use enables the sensitive and target specific observation of biological events at the molecular and cellular levels.

    2. Reticular Chemistry of Metal–Organic Polyhedra (pages 5136–5147)

      David J. Tranchemontagne, Zheng Ni, Michael O'Keeffe and Omar M. Yaghi

      Article first published online: 4 JUN 2008 | DOI: 10.1002/anie.200705008

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      Made to measure: Analysis of structures of existing metal–organic polyhedra (MOPs) delivers important criteria for the design of new MOPs. The angle between the links from the secondary building unit and that between the links of a ditopic linker linker are important parameters for the design of such structures.

  8. Communications

    1. Top of page
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    4. Graphical Abstract
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    6. Book Review
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    8. Reviews
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    1. Alignment of Carbon Nanotubes in Weak Magnetic Fields (pages 5148–5152)

      John Tumpane, Nikolaos Karousis, Nikos Tagmatarchis and Bengt Nordén

      Article first published online: 11 JUN 2008 | DOI: 10.1002/anie.200801548

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      Gently brought into line: Functionalized carbon nanotubes (see picture, C,H black, N blue) facilitate a high degree of orientation in a weak magnetic field equation image, as detected by linear dichroism spectroscopy (incident planes of light A and A). In addition, relaxation measurements in the magnetic field allow the length of the nanotubes to be determined.

    2. “Conformational” Solvatochromism: Spatial Discrimination of Nonpolar Solvents by Using a Supramolecular Box of a π-Conjugated Zinc Bisporphyrin Rotamer (pages 5153–5156)

      Junko Aimi, Yuka Nagamine, Akihiko Tsuda, Atsuya Muranaka, Masanobu Uchiyama and Takuzo Aida

      Article first published online: 11 JUN 2008 | DOI: 10.1002/anie.200801332

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      Boxing clever: A cyclic tetramer of the dialkynylene-bridged zinc bisporphyrin rotamer [ZnP([TRIPLE BOND])2] shows a unique solvatochromic response to nonpolar solvents with equally low dielectric constants (2.23–2.57). This solvatochromism originates from the π conjugation of [ZnP ([TRIPLE BOND])2]. The tetramer [{ZnP([TRIPLE BOND])2}4] can discriminate spectroscopically benzene from CCl4 (see picture) and even the regioisomers of xylene.

    3. DNA-Tile-Directed Self-Assembly of Quantum Dots into Two-Dimensional Nanopatterns (pages 5157–5159)

      Jaswinder Sharma, Yonggang Ke, Chenxiang Lin, Rahul Chhabra, Qiangbin Wang, Jeanette Nangreave, Yan Liu and Hao Yan

      Article first published online: 4 JUN 2008 | DOI: 10.1002/anie.200801485

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      Turning dots into stripes: Rationally designed DNA-tile arrays are used to organize quantum dots into well-aligned two-dimensional nanopatterns (see schematic representation and TEM image; A: streptavidin-coated quantum dots); the power of programmable DNA scaffolding is thereby demonstrated.

    4. Organogelation of Sheet–Helix Diblock Copolypeptides (pages 5160–5162)

      Matthew I. Gibson and Neil R. Cameron

      Article first published online: 4 JUN 2008 | DOI: 10.1002/anie.200801056

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      Together they're strong: Block copolypeptides containing poly(benzyl-L-threonine) and an α-helical block are effective organogelators despite the high solubility of the constituent homopolymers. An unexpected conformational change in the first block, from random coil to β sheet, directs the assembly into stacked lamellae (see picture).

    5. Charge-Conversion Ternary Polyplex with Endosome Disruption Moiety: A Technique for Efficient and Safe Gene Delivery (pages 5163–5166)

      Yan Lee, Kanjiro Miyata, Makoto Oba, Takehiko Ishii, Shigeto Fukushima, Muri Han, Hiroyuki Koyama, Nobuhiro Nishiyama and Kazunori Kataoka

      Article first published online: 4 JUN 2008 | DOI: 10.1002/anie.200800963

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      Wrapped for special delivery: A ternary polyplex, with an endosomal disruption moiety based on the charge-conversion polymer pAsp(DET-Aco), showed negative charges for serum stability and low cytotoxicity, but the charges became positive and the endosome disruption moiety was exposed (see picture). High transfection efficiency and minimal cytotoxicity were observed with primary cells.

    6. Two-Photon Fluorescent Probes for Intracellular Free Zinc Ions in Living Tissue (pages 5167–5170)

      Hwan Myung Kim, Mun Sik Seo, Myoung Jin An, Jin Hee Hong, Yu Shun Tian, Joon Ho Choi, Ohyun Kwon, Kyoung J. Lee and Bong Rae Cho

      Article first published online: 4 JUN 2008 | DOI: 10.1002/anie.200800929

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      The living image: The efficient two-photon probes AZn1 and AZn2 (see picture for rat brain tissue) show 24- to 52-fold two-photon excited fluorescence enhancement in response to Zn2+. They can selectively detect intracellular free Zn2+ ions in live cells and in living tissues at a depth of 80–150 μm without interference from other metal ions and the membrane-bound probes.

    7. Nb(salan)-Catalyzed Asymmetric Epoxidation of Allylic Alcohols with Hydrogen Peroxide (pages 5171–5174)

      Hiromichi Egami and Tsutomu Katsuki

      Article first published online: 5 JUN 2008 | DOI: 10.1002/anie.200800797

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      Bridging the catalyst: The dimeric complex [(μ-oxo){Nb(salan)}2] catalyzes asymmetric epoxidation of allylic alcohols by hydrogen peroxide to give epoxy alcohols with good to high enantioselectivities irrespective of the olefin geometry (see scheme).

    8. Stimuli-Responsive Luminescent Liquid Crystals: Change of Photoluminescent Colors Triggered by a Shear-Induced Phase Transition (pages 5175–5178)

      Yoshimitsu Sagara and Takashi Kato

      Article first published online: 2 JUN 2008 | DOI: 10.1002/anie.200800164

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      Shear brilliance: The photoluminescent color of a pyrene-based liquid crystal changes from yellow to blue-green upon mechanical shearing due to a phase transition from a micellar cubic to a columnar phase (see picture).

    9. A Complete Catalytic Cycle for Supramolecular Methanol-to-Olefins Conversion by Linking Theory with Experiment (pages 5179–5182)

      David M. McCann, David Lesthaeghe, Philip W. Kletnieks, Darryl R. Guenther, Miranda J. Hayman, Veronique Van Speybroeck, Michel Waroquier and James F. Haw

      Article first published online: 28 APR 2008 | DOI: 10.1002/anie.200705453

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      Le Tour de MTO: A complete working catalytic cycle for the conversion of methanol to olefins in HZSM-5 is reported in full consistency with both experimental and theoretical observations. This particular route includes carbon-atom scrambling into a methylbenzene ring, NMR-observed cationic intermediates, and the production of isobutene.

    10. Vertically Aligned Diamond Nanowires for DNA Sensing (pages 5183–5185)

      Nianjun Yang, Hiroshi Uetsuka, Eiji Osawa and Christoph E. Nebel

      Article first published online: 6 JUN 2008 | DOI: 10.1002/anie.200801706

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      Live wire: Biofunctionalized vertically aligned diamond nanowires as DNA sensors benefit from the outstanding electrochemical properties of diamond as a transducer as well as the advantages of dispersed, controlled binding of linker molecules to achieve behavior of DNA molecules' “like-in-solution” situation.

    11. Microbial Synthesis of CdS Nanocrystals in Genetically Engineered E. coli (pages 5186–5189)

      Seung Hyun Kang, Krassimir N. Bozhilov, Nosang V. Myung, Ashok Mulchandani and Wilfred Chen

      Article first published online: 2 JUN 2008 | DOI: 10.1002/anie.200705806

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      A bacterial biofactory: Escherichia coli strains were genetically engineered to produce phytochelatins (PCs) as capping agents and used for the intracellular synthesis of fluorescent and water-soluble PC-coated CdS nanoparticles (see figure). The size of the semiconductor nanocrystals could be tuned by controlling the population of the capping PCs. SpPCS is the PC synthase from Schizosaccharomyces pombe; GSHI*=γ-glutamylcysteine synthetase.

    12. Enrichment of Cell-Targeting and Population-Specific Aptamers by Fluorescence-Activated Cell Sorting (pages 5190–5193)

      Marie-Sophie L. Raddatz, Andreas Dolf, Elmar Endl, Percy Knolle, Michael Famulok and Günter Mayer

      Article first published online: 2 JUN 2008 | DOI: 10.1002/anie.200800216

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      A class above: In a sophisticated approach to the systematic evolution of ligands by exponential enrichment (SELEX) of cell-type-specific nucleic acid aptamers, the title technique was combined with the use of combinatorial nucleic acid libraries to target a defined subpopulation within composite mixtures of cells (see picture). The ssDNA library after 10 selection cycles bound vital Burkitt lymphoma cells more effectively than the starting library.

    13. Gold(0) Nanoparticles for Selective Catalytic Diboration (pages 5194–5197)

      Jesus Ramírez, Mercedes Sanaú and Elena Fernández

      Article first published online: 5 JUN 2008 | DOI: 10.1002/anie.200800541

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      Going with gold: Gold(0) nanoparticles stabilized with the diphosphine ligand binap mediate the catalytic diboration of styrene, resulting in complete formation of the bis(boronate)ester product. The gold(0) catalytic mechanism can involve base-assisted heterolytic cleavage of diboron reagents followed by the transmetalation step.

    14. Transformation of a 1-Zirconacyclopent-3-yne, a Five-Membered Cycloalkyne, into a 1-Zirconacyclopent-3-ene and Formal “1-Zirconacyclopenta-2,3-dienes” (pages 5198–5202)

      Noriyuki Suzuki, Daisuke Hashizume, Hiroyuki Koshino and Teiji Chihara

      Article first published online: 30 APR 2008 | DOI: 10.1002/anie.200800739

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      Alkyne, alkene, and “allene”? A stable five-membered metallacycloalkyne 1 with alkylidene moieties was treated with an alkali metal to give a dianionic species 2, which was transformed into a 1-zirconacyclopent-3-ene complex by protonation. The alkylation of 2 afforded zirconocene–η4-1,3-enyne complexes 3, which can be regarded as formal “1-zirconacyclopenta-2,3-dienes”. Ar=4-EtC6H4; R=Me, Me3Sn.

    15. Complete Switch of Migratory Aptitude in Aluminum-Catalyzed 1,2-Rearrangement of Differently α,α-Disubstituted α-Siloxy Aldehydes (pages 5203–5206)

      Kohsuke Ohmatsu, Takayuki Tanaka, Takashi Ooi and Keiji Maruoka

      Article first published online: 4 JUN 2008 | DOI: 10.1002/anie.200800801

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      Control of the migration tendency: The regiodivergent 1,2-rearrangement of α-siloxy aldehydes bearing α-aryl and α-alkyl substituents into α-siloxy ketones has been realized by using different aluminum Lewis acid catalyst/solvent systems (see scheme). The scope of this unprecedented protocol has been investigated with various substrates and clearly demonstrates its utility for the selective synthesis of two structural isomers from one substrate.

    16. Simple and Efficient Asymmetric α-Alkylation and α,α-Bisalkylation of Acyclic Ketones by Using Chiral N-Amino Cyclic Carbamate Hydrazones (pages 5207–5210)

      Daniel Lim and Don M. Coltart

      Article first published online: 4 JUN 2008 | DOI: 10.1002/anie.200800848

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      Distinguishing left from right: In the title reactions, chiral N-amino cyclic carbamates (ACCs) substantially diminish the drawbacks associated with the use of chiral dialkyl hydrazines, yet provide excellent stereoselectivity and high yields. In addition, ACCs exhibit a unique directing effect that overrides the inherent selectivity of lithium diisopropylamide (LDA) and enables the asymmetric α,α-bisalkylation of ketones (see scheme).

    17. Electrochemically Driven Release of Picomole Amounts of Calcium Ions with Temporal and Spatial Resolution (pages 5211–5214)

      Christian Amatore, Damiano Genovese, Emmanuel Maisonhaute, Noureddine Raouafi and Bernd Schöllhorn

      Article first published online: 2 JUN 2008 | DOI: 10.1002/anie.200705274

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      Controlled delivery: Redox commutation of a paraphenylenediamine and aza-crown ether assembly anchored as a self-assembled monolayer to an electrode surface allows the time and spatially controlled release of picomole amounts of calcium ions. The release occurs on a sub-millisecond time scale, and is irreversible provided that the two-electron-oxidized redox center is not returned electrochemically to its neutral initial state (see scheme).

    18. PdII-Catalyzed Monoselective ortho Halogenation of C[BOND]H Bonds Assisted by Counter Cations: A Complementary Method to Directed ortho Lithiation (pages 5215–5219)

      Tian-Sheng Mei, Ramesh Giri, Nathan Maugel and Jin-Quan Yu

      Article first published online: 3 JUN 2008 | DOI: 10.1002/anie.200705613

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      When the counterion counts: The yield and selectivity of the title transformation of benzoic acid derivatives were improved greatly by using tetraalkyl ammonium salts as additives (see scheme; monoselectivity: 5:1–18:1). These effects are attributed to the influence of counter cations. The halogenated products are versatile intermediates for the construction of substituted aromatic compounds. DMF=N,N-dimethylformamide.

    19. Carbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Enynes as Surrogates to Preformed Allenylmetal Reagents: A Ruthenium-Catalyzed C[BOND]C Bond-Forming Transfer Hydrogenation (pages 5220–5223)

      Ryan L. Patman, Vanessa M. Williams, John F. Bower and Michael J. Krische

      Article first published online: 4 JUN 2008 | DOI: 10.1002/anie.200801359

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      Transcending oxidation level: Under the conditions of ruthenium-catalyzed transfer hydrogenation, conjugated enynes couple to benzylic, allylic, and aliphatic alcohols or aldehydes to furnish products of carbonyl propargylation (see scheme; dppf=1,1′-bis(diphenylphosphino)ferrocene, TBS=tert-butyldimethylsilyl). Isotopic labeling studies corroborate a mechanism involving hydrogen donation from the alcohol to the enyne.

    20. Homogeneous Catalytic Hydroamination of Alkynes and Allenes with Ammonia (pages 5224–5228)

      Vincent Lavallo, Guido D. Frey, Bruno Donnadieu, Michele Soleilhavoup and Guy Bertrand

      Article first published online: 4 JUN 2008 | DOI: 10.1002/anie.200801136

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      A golden ticket to the synthesis of reactive nitrogen-containing compounds, such as imines, enamines, and allyl amines, through the addition of NH3 to unsaturated bonds is the cationic cyclic (alkyl)(amino)carbene–gold(I) catalyst shown in blue (Dipp=diisopropylphenyl). An ideal initial step for the preparation of simple bulk chemicals, this reaction is also useful for the synthesis of more complex molecules (see examples).

    21. Construction and Screening of a 2-Aminoimidazole Library Identifies a Small Molecule Capable of Inhibiting and Dispersing Bacterial Biofilms across Order, Class, and Phylum (pages 5229–5231)

      Steven A. Rogers and Christian Melander

      Article first published online: 4 JUN 2008 | DOI: 10.1002/anie.200800862

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      A team of three: 2-Aminoimidazole, triazole, and tether units together resulted in conjugates (see picture, n=4–6 for the most active compounds) that are capable of inhibiting and dispersing bacteria biofilms without inducing bacterial death. Such biofilms have been implicated in a plethora of medical problems, including infection of implanted medical devices and the mortality of cystic fibrosis patients.

    22. Cage Escape Competes with Geminate Recombination during Alkane Hydroxylation by the Diiron Oxygenase AlkB (pages 5232–5234)

      Rachel N. Austin, Kate Luddy, Karla Erickson, Marilla Pender-Cudlip, Erin Bertrand, Dayi Deng, Ryan S. Buzdygon, Jan B. van Beilen and John T. Groves

      Article first published online: 2 JUN 2008 | DOI: 10.1002/anie.200801184

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      AlkB stops the radical clock: Three structurally analogous radical-clock substrates with a large span in their rearrangement rates are hydroxylated by AlkB to afford similar amounts of rearranged (2) and unrearranged products (1). Such a result is in accord with radical rebound competing with cage escape of the geminate substrate radical. The results show that radical clocks can measure both the radical lifetime and the kinetics of cage escape.

    23. Time-Resolved Dynamic Nuclear Polarization Enhanced NMR Spectroscopy (pages 5235–5237)

      Sean Bowen and Christian Hilty

      Article first published online: 2 JUN 2008 | DOI: 10.1002/anie.200801492

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      The sensitive touch: Sensitivity constraints in NMR spectroscopy typically call for long measurement times. Hyperpolarization can enhance the time resolution of NMR spectroscopy by removing the need for signal averaging. Reactions such as enzyme catalysis can be followed in real time by hyperpolarized NMR spectroscopy through reduction in the intensity of the substrate resonance as well as the appearance of product resonances (see picture).

    24. Which Oxidant Is Really Responsible for P450 Model Oxygenation Reactions? A Kinetic Approach (pages 5238–5242)

      Alicja Franke, Christoph Fertinger and Rudi van Eldik

      Article first published online: 2 JUN 2008 | DOI: 10.1002/anie.200800907

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      A rate-fate fête: Direct kinetic studies on epoxidation and sulfoxidation reactions revealed that the oxygenating capability of [(TMP+.)FeIV[DOUBLE BOND]O] is orders of magnitude higher than that of [FeIII(TMP)(m-CPBA)]. Under catalytic turnover conditions, the relative ratio between the rate of O[BOND]O bond heterolytic cleavage and the rate of oxygen transfer from the [FeIII(TMP)(m-CPBA)] intermediate to the substrate, should be taken into consideration. m-CPBA=m-chloroperbenzoic acid, TMP=meso-tetramesitylporphyrin.

    25. Cobalt-Catalyzed [4+2+2] Cycloaddition for the Synthesis of 1,3,6-Cyclooctatrienes (pages 5243–5245)

      Gerhard Hilt and Judith Janikowski

      Article first published online: 5 JUN 2008 | DOI: 10.1002/anie.200800127

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      After eight? Polysubstituted 1,3,6-cyclooctatrienes can be obtained in high regioselectivity and in good yields from a cobalt-catalyzed intermolecular cycloaddition reaction between two alkynes and a 1,3-diene (see example in scheme).

    26. Total Synthesis of Polyoxygenated Cembrenes (pages 5246–5249)

      Lutz F. Tietze, C. Christian Brazel, Sören Hölsken, Jörg Magull and Arne Ringe

      Article first published online: 4 JUN 2008 | DOI: 10.1002/anie.200800626

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      A convergent approach for the stereoselective construction of polyoxygenated cembrenes is reported. Key steps in the synthesis are an asymmetric domino multicomponent allylation, a modified Myers α-alkylation, and a ring-closing metathesis.

    27. Selenium as a Key Element for Highly Ordered Aromatic Self-Assembled Monolayers (pages 5250–5252)

      Asif Bashir, Daniel Käfer, Jan Müller, Christof Wöll, Andreas Terfort and Gregor Witte

      Article first published online: 2 JUN 2008 | DOI: 10.1002/anie.200800883

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      Less stress: Self-assembled monolayers of aromatic molecules become significantly better ordered, if selenium atoms instead of sulfur atoms are used as anchoring groups. Presumably as a result of a lowered corrugation for the Au–Se interaction, the molecules can adapt more easily to structures governed by the carbon backbone.

    28. Mechanistic Studies of Hydrocarbon Combustion and Synthesis on Noble Metals (pages 5253–5255)

      Oliver R. Inderwildi, Stephen J. Jenkins and David A. King

      Article first published online: 4 JUN 2008 | DOI: 10.1002/anie.200800685

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      Common staging point: Results of DFT studies on surface-catalyzed processes indicate that oxymethylidyne species (CHO) are intermediates in both the combustion and the synthesis of hydrocarbons on noble-metal surfaces (the picture shows CHO formation on Pd). Combustion and synthesis proceed by very similar pathways, but in opposite directions, even though different metals are used in the two processes.

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    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlight
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      Preview: Angew. Chem. Int. Ed. 29/2008 (page 5259)

      Article first published online: 23 JUN 2008 | DOI: 10.1002/anie.200890136

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