Angewandte Chemie International Edition

Cover image for Vol. 46 Issue 9

February 19, 2007

Volume 46, Issue 9

Pages 1351–1543

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Review
    9. Communications
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    1. Cover Picture: Cross-Linked Layered Structure of Magnetically Ordered [Fe(TCNE)2]⋅z CH2Cl2 Determined by Rietveld Refinement of Synchrotron Powder Diffraction Data (Angew. Chem. Int. Ed. 9/2007) (page 1351)

      Jae-Hyuk Her, Peter W. Stephens, Konstantin I. Pokhodnya, Michael Bonner and Joel S. Miller

      Article first published online: 9 FEB 2007 | DOI: 10.1002/anie.200790027

      A layered magnet is formed from the reaction (see H-tube apparatus; bottom) of tetracyanoethylene (TCNE; left) and [Fe(CO)5] (right). The structural elucidation described by P. W. Stephens, J. S. Miller, and co-workers in their Communication on page 1521 ff. reveals that magnetic layers of [TCNE].− bonded to four high-spin FeII ions are connected by [C4(CN)8]2−, the diamagnetic σ dimer of [TCNE].−, which explains the higher than expected magnetization for this ferrimagnet.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Review
    9. Communications
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    1. Inside Cover: Reduction of Phenyl Silyl Acetylenes with Lithium: Unexpected Formation of a Dilithium Dibenzopentalenide (Angew. Chem. Int. Ed. 9/2007) (page 1352)

      Masaichi Saito, Michio Nakamura, Tomoyuki Tajima and Michikazu Yoshioka

      Article first published online: 9 FEB 2007 | DOI: 10.1002/anie.200790028

      Reduction of phenyl silyl acetylenes with lithium led to the unexpected formation of a dilithium dibenzopentalenide derivative together with the expected 1,4-dilithio-1,3-butadiene. The bulkiness of the silyl substituent of the phenyl silyl acetylene strongly affects its reduction mode. Further details may be found in the Communication by M. Saito and co-workers on page 1504 ff.

  3. Graphical Abstract

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    4. Graphical Abstract
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    1. Graphical Abstract: Angew. Chem. Int. Ed. 9/2007 (pages 1355–1364)

      Article first published online: 9 FEB 2007 | DOI: 10.1002/anie.200790029

  4. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Review
    9. Communications
    10. Preview
  5. Book Reviews

    1. Top of page
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    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Review
    9. Communications
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  6. Highlights

    1. Top of page
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    5. News
    6. Book Reviews
    7. Highlights
    8. Review
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    1. Thermally Responsive Polymer Vesicles (pages 1370–1372)

      Yotaro Morishima

      Article first published online: 23 JAN 2007 | DOI: 10.1002/anie.200603405

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      Guilty as charged; lock them up! Recent advances in the field of polymer vesicles are highlighted with particular focus on the temperature-induced, direct formation of vesicles in water from amphiphilic block copolymers and the structural “locking” of the resulting vesicles by formation of polyelectrolyte complexes (see picture).

    2. New Approaches for Decarboxylative Biaryl Coupling (pages 1373–1375)

      Olivier Baudoin

      Article first published online: 24 JAN 2007 | DOI: 10.1002/anie.200604494

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      Closer to nature: Biaryl motifs are common in organic molecules with important biological and physical properties. Carboxylic acids can now be used as aryl donors in palladium-catalyzed cross-coupling reactions to give biaryl compounds of high synthetic value (see scheme).

  7. Review

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    1. You have free access to this content
      The Woodward–Doering/Rabe–Kindler Total Synthesis of Quinine: Setting the Record Straight (pages 1378–1413)

      Jeffrey I. Seeman

      Article first published online: 9 FEB 2007 | DOI: 10.1002/anie.200601551

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      Did they or didn't they? In 1944, R. B. Woodward and W. von E. Doering reported the total synthesis of homomeroquinene and d-quinotoxine. On the basis of the conversion of d-quinotoxine into quinine reported by P. Rabe and K. Kindler in 1918, Woodward and Doering made the claim of the total synthesis of quinine (1). In 2000, G. Stork concluded that this claim was a myth. Previously unpublished archive material and numerous interviews throw new light onto this controversy.

  8. Communications

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    1. γ-Substituted Peptide Nucleic Acids Constructed from L-Lysine are a Versatile Scaffold for Multifunctional Display (pages 1414–1418)

      Ethan A. Englund and Daniel H. Appella

      Article first published online: 29 NOV 2006 | DOI: 10.1002/anie.200603483

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      On display: This model shows DNA (pink) annealed to a peptide nucleic acid (PNA; orange) containing several L-lysine γ side chains (LKγ-PNA) in the middle of the PNA oligomer. The LKγ-PNA side chains project away from the nucleobase pairs (purple) and line the periphery of the duplex. This strategy can be used for the multifunctional display of various functional groups from the PNA residues without diminishing the binding affinity or selectivity to DNA.

    2. Observation of Cu2+–H2 Interactions in a Fully Desolvated Sodalite-Type Metal–Organic Framework (pages 1419–1422)

      Mircea Dincă, Won Seok Han, Yun Liu, Anne Dailly, Craig M. Brown and Jeffrey R. Long

      Article first published online: 19 JAN 2007 | DOI: 10.1002/anie.200604362

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      Metal–H2binding: A new tetrazolate-based metal–organic framework exhibits high H2 uptake at low temperature and moderate pressure. The evacuation of coordinated solvent molecules from Cu2+ ions within the framework provides strong binding sites for H2 molecules (see picture; Cu purple, C gray, N blue, Cl green).

    3. The Oxorhenium(VII)-Catalyzed Direct Condensation of Phosphoric Acid with an Alcohol (pages 1423–1426)

      Akira Sakakura, Mikimoto Katsukawa and Kazuaki Ishihara

      Article first published online: 17 JAN 2007 | DOI: 10.1002/anie.200604333

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      Come together … over Re: Oxorhenium(VII) complexes catalyze the direct condensation of phosphoric acid with an alcohol to selectively give the corresponding phosphoric acid monoester on a 2–100-mmol scale (see scheme). This method should be useful for the industrially important synthesis of phosphoric acid monoesters.

    4. Towards a 32-Electron Principle: Pu@Pb12 and Related Systems (pages 1427–1430)

      Jean-Pierre Dognon, Carine Clavaguéra and Pekka Pyykkö

      Article first published online: 16 JAN 2007 | DOI: 10.1002/anie.200604198

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      The predicted endohedral icosahedral clusters Pu@Pb12 (see picture; Pu blue, Pb yellow) and [Am@Pb12]+ have an outermost 32-electron system corresponding to formally occupied 7s, 7p, 6d, and 5f actinide orbitals, each of which interacts with a Pb 6p-based orbital of the [Pb12]2− cage. This study provides the first example of a formal 32-electron principle, and 32 is not a false magic number.

    5. Supramolecular Liquid Crystals Based on Cyclo[8]pyrrole (pages 1431–1435)

      Marcin Stępień, Bertrand Donnio and Jonathan L. Sessler

      Article first published online: 16 JAN 2007 | DOI: 10.1002/anie.200603893

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      It stacks up nicely: Exposure of dihydrogen sulfate salts of appropriately substituted cyclo[8]pyrroles to electron-deficient acceptor molecules gives discotic liquid crystals. The columnar mesophase structures are stabilized by electron-donor/electron-acceptor interactions (see picture; red: trinitrobenzene, green: cyclo[8]pyrrole cores, yellow: sulfate ions, gray: volume occupied by the substituents).

    6. [Os3(CO)6(PMe3)3](μ3222-C60)[Re3(μ-H)3(CO)9]: A Fullerene[60] Coordinated to Two Different Trinuclear Clusters (pages 1436–1439)

      Bo Keun Park, Chang Yeon Lee, Jaehoon Jung, Jung Hak Lim, Young-Kyu Han, Chang Seop Hong and Joon T. Park

      Article first published online: 17 JAN 2007 | DOI: 10.1002/anie.200603882

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      A buckyball sandwich: The depicted reaction produces cis-1 and cis-2 (see picture), in which the fullerene is sandwiched between two different clusters. Variable-temperature 1H NMR spectra reveal that cis-1 and cis-2 are interconvertible and cis-2 exists as two isomers.

    7. A Site- and Stereoselective Intermolecular Alkene–Alkyne Coupling Process (pages 1440–1443)

      Holly A. Reichard and Glenn C. Micalizio

      Article first published online: 15 JAN 2007 | DOI: 10.1002/anie.200603515

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      Ti-ght union: A highly regio- and stereoselective bimolecular coupling reaction is described for the union of substituted, unactivated olefins and internal alkynes (see scheme). The titanium-mediated coupling reaction proceeds with C[BOND]C bond formation occurring distal to a pendent hydroxy group.

    8. On the Rearrangement of an Azaspiroindolenine to a Precursor to Phalarine: Mechanistic Insights (pages 1444–1447)

      Chaomin Li, Collin Chan, Annekatrin C. Heimann and Samuel J. Danishefsky

      Article first published online: 19 JAN 2007 | DOI: 10.1002/anie.200604071

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      An interesting rearrangement: Management of functional groups in derivatives of indoles enables a rearrangement to take place which provides the pentacyclic ring system found in phalarine (see scheme, CSA=camphorsulfonic acid, Ts=toluene-4-sulfonyl). Studies into the mechanism proved valuable for the total synthesis of phalarine and provided insight into the chemistry of indoles in general.

    9. Total Synthesis of Phalarine (pages 1448–1450)

      Chaomin Li, Collin Chan, Annekatrin C. Heimann and Samuel J. Danishefsky

      Article first published online: 19 JAN 2007 | DOI: 10.1002/anie.200604072

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      End of the expedition … for now: Completion of the first total synthesis of phalarine from an advanced rearrangement product brought up interesting obstacles to overcome. Use of the Gassman oxindole synthesis and subsequent manipulations led to the racemic natural product (see scheme, Ts=toluene-4-sulfonyl).

    10. Total Synthesis of Peribysin E Necessitates Revision of the Assignment of its Absolute Configuration (pages 1451–1454)

      Angie R. Angeles, David C. Dorn, Cynthia A. Kou, Malcolm A. S. Moore and Samuel J. Danishefsky

      Article first published online: 19 JAN 2007 | DOI: 10.1002/anie.200604308

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      The right way round: Peribysin E, a naturally occurring adhesion inhibitor, has been synthesized and, as a result, its absolute configuration reassigned. The natural and nonnatural enantiomers can be reached starting from (R)- or (S)-carvone, respectively. A key step is the ring contraction of 1 to 2 (see scheme, TBS=tert-butyldimethylsilyl, TES=triethylsilyl).

    11. Controlled Release of Guest Molecules from Mesoporous Silica Particles Based on a pH-Responsive Polypseudorotaxane Motif (pages 1455–1457)

      Chiyoung Park, Kyoungho Oh, Sang Cheon Lee and Chulhee Kim

      Article first published online: 15 JAN 2007 | DOI: 10.1002/anie.200603404

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      Stringing them along: The pores of a mesoporous silica particle were filled with guest molecules and then blocked by threading cyclodextrin molecules (CDs) onto the surface-grafted polyethylenimine (PEI) chains at pH 11. At pH 5.5, the guest molecules can be released from the pores of the particle by reversible dethreading of the CDs from the PEI chains.

    12. Base-Induced Solvent Switches in Acid–Base Reactions (pages 1458–1461)

      Omar F. Mohammed, Dina Pines, Erik T. J. Nibbering and Ehud Pines

      Article first published online: 10 JAN 2007 | DOI: 10.1002/anie.200603383

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      Fast switches: Eigen and Weller's classic diffusion reaction model for aqueous acid–base neutralization reactions is used to interpret the proton-transfer dynamics between pyranine and trichloroacetate. Upon mutual diffusion of the acid and base to form an encounter reaction complex, solvent switches mediate the proton transfer between acid and base and provide a general framework for all observed dynamic features (see picture; ROH=acid, B=base).

    13. Characterization of the Enzyme BtrD from Bacillus circulans and Revision of Its Functional Assignment in the Biosynthesis of Butirosin (pages 1462–1464)

      Andrew W. Truman, Fanglu Huang, Nicholas M. Llewellyn and Jonathan B. Spencer

      Article first published online: 17 JAN 2007 | DOI: 10.1002/anie.200604194

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      A functional reassignment: BtrD, a protein encoded in the butirosin gene cluster, functions as a deacetylase rather than a nucleotidyltransferase as previously reported. BtrD was found to selectively catalyze the conversion of 2′-N-acetylparomamine to paromamine, strongly suggesting that butirosin's neosamine moiety originates from uridine diphospho(UDP)-N-acetylglucosamine (see picture).

    14. Dichloromethane as a Selective Modifying Agent To Create a Family of Highly Reactive Chromium Polymerization Sites (pages 1465–1468)

      Cristina N. Nenu, Elena Groppo, Carlo Lamberti, Andrew M. Beale, Tom Visser, Adriano Zecchina and Bert M. Weckhuysen

      Article first published online: 9 JAN 2007 | DOI: 10.1002/anie.200602593

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      Uniform polymerization sites with high activity can be created by treating a Phillips-type CrII/SiO2 catalyst with CH2Cl2 (as shown schematically in the picture) under well-defined conditions. A mechanism is proposed in which CH2Cl2 increases the catalytic activity of a small fraction of Cr sites while poisoning the remainder.

    15. Reaching the Maximum Multiplicity of the Covalent Chemical Bond (pages 1469–1472)

      Björn O. Roos, Antonio C. Borin and Laura Gagliardi

      Article first published online: 16 JAN 2007 | DOI: 10.1002/anie.200603600

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      Maxing out at six: The maximum bond order that can be achieved between two equal atoms in the periodic system is six. The picture shows the potential energy curves for the diatoms Cr2, Mo2, and W2, where the latter two are sextuply bonded molecules (d=internuclear distance in atomic units).

    16. A General Method for Measurement of Enantiomeric Excess by Using Electrooptics in Ferroelectric Liquid Crystals (pages 1473–1475)

      David M. Walba, Lior Eshdat, Eva Korblova, Renfan Shao and Noel A. Clark

      Article first published online: 15 JAN 2007 | DOI: 10.1002/anie.200603692

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      It'seerie: A new method for quantitative measurement of ee values is described. The method exploits the unique electrooptic properties of the chiral smectic A liquid-crystal phase and is potentially applicable to the high-throughput (>106 determinations per day) measurement of ee values for any chiral analyte.

    17. High-Pressure Synthesis of Crystalline Carbon Nitride Imide, C2N2(NH) (pages 1476–1480)

      Elisabeta Horvath-Bordon, Ralf Riedel, Paul F. McMillan, Peter Kroll, Gerhard Miehe, Peter A. van Aken, Andreas Zerr, Peter Hoppe, Olga Shebanova, Ian McLaren, Stefan Lauterbach, Edwin Kroke and Reinhard Boehler

      Article first published online: 15 JAN 2007 | DOI: 10.1002/anie.200603851

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      Extreme chemistry: The carbon nitride imide C2N2(NH) is synthesized from the single-source precursor 1-cyanoguanidine under high-pressure and high-temperature conditions in a laser-heated diamond-anvil cell. Characterization of single crystals recovered at ambient conditions reveals that the new compound adopts a defect wurtzite structure (see picture).

    18. Backbone Carbonyl Group Basicities Are Related to Gas-Phase Fragmentation of Peptides and Protein Folding (pages 1481–1484)

      Mikhail M. Savitski, Frank Kjeldsen, Michael L. Nielsen, Sergiy O. Garbuzynskiy, Oxana V. Galzitskaya, Alexey K. Surin and Roman A. Zubarev

      Article first published online: 9 JAN 2007 | DOI: 10.1002/anie.200603881

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      A strong correlation is found between the propensity of individual amino acids to induce peptide-bond cleavage in the gas phase (PAA–XX) and their structure-forming propensity (PS, red) and H-bond-accepting propensity (PH, blue). Thus, the same fundamental parameter, carbonyl group basicity, governs the formation of secondary protein structures in solution and directs fragmentation in the gas phase.

    19. Stereochemical and Mechanistic Investigations of a Palladium-Catalyzed Annulation of Secondary Alkyl Iodides (pages 1485–1488)

      Alena Rudolph, Nils Rackelmann and Mark Lautens

      Article first published online: 15 JAN 2007 | DOI: 10.1002/anie.200603888

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      Inversion versus retention: A palladium-catalyzed annulation with enantioenriched secondary alkyl iodides gives mechanistic insight into the stereochemistry of this C[BOND]H bond functionalization reaction (see scheme) involving a proposed PdII/PdIV catalytic cycle.

    20. Template Synthesis of Multishelled Cu2O Hollow Spheres with a Single-Crystalline Shell Wall (pages 1489–1492)

      Haolan Xu and Wenzhong Wang

      Article first published online: 17 JAN 2007 | DOI: 10.1002/anie.200603895

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      Shells within shells: Simply varying the concentration of the cetyltrimethylammonium bromide surfactant in a template process leads to single-, double-, triple-, and quadruple-shelled Cu2O hollow spheres (see TEM image). Thus, the vesicle-directed synthesis of inorganic multishelled hollow spheres is feasible.

    21. Crystalline Mo3VOx Mixed-Metal-Oxide Catalyst with Trigonal Symmetry (pages 1493–1496)

      Masahiro Sadakane, Nobufumi Watanabe, Tomokazu Katou, Yoshinobu Nodasaka and Wataru Ueda

      Article first published online: 15 JAN 2007 | DOI: 10.1002/anie.200603923

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      Outstanding catalytic activity for the selective oxidation of acrolein (see picture) is observed with a crystalline metal oxide, Mo3VOx (x≤11.1). The catalyst is synthesized from a solution containing pentagonal units of {Mo(Mo5O27)} (blue), which further react with molybdenum and vanadium species (red) to form a 3D metal oxide.

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      High Enantioselectivity Is Induced by a Single Monodentate Phosphoramidite Ligand in Iridium-Catalyzed Asymmetric Hydrogenation (pages 1497–1500)

      Francesca Giacomina, Auke Meetsma, Lavinia Panella, Laurent Lefort, André H. M. de Vries and Johannes G. de Vries

      Article first published online: 16 JAN 2007 | DOI: 10.1002/anie.200603930

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      The Full Monty? Stripping a catalyst down to its bare essentials gives a neutral iridium complex containing only one monodentate phosphoramidite ligand that is an efficient catalyst for the enantioselective hydrogenation of α-dehydroamino acids (see picture).

    23. Aligned Carbon Nanotubes in the Supramolecular Order of Discotic Liquid Crystals (pages 1501–1503)

      Sandeep Kumar and Hari Krishna Bisoyi

      Article first published online: 16 JAN 2007 | DOI: 10.1002/anie.200603967

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      Between the lines: Functionalized single-walled carbon nanotubes (SWNTs) can be aligned in the hexagonal columnar mesophase of discotic liquid crystals (DLCs). The thermophysical properties of SWNT–DLC composites indicate inclusion of SWNTs in the supramolecular order of DLCs (see picture).

    24. Reduction of Phenyl Silyl Acetylenes with Lithium: Unexpected Formation of a Dilithium Dibenzopentalenide (pages 1504–1507)

      Masaichi Saito, Michio Nakamura, Tomoyuki Tajima and Michikazu Yoshioka

      Article first published online: 24 JAN 2007 | DOI: 10.1002/anie.200604067

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      The degree of bulkiness of the silyl substituent strongly affects the reduction mode of phenyl silyl acetylenes. For example, the treatment of phenyl(triisopropylsilyl)acetylene with lithium led to the unprecedented formation of a dilithium dibenzopentalenide together with the expected 1,4-dilithio-1,3-butadiene (see scheme), whereas the reduction of phenyl(tert-butyldimethylsilyl)acetylene gave only the corresponding 1,4-dilithio-1,3-butadiene.

    25. Adaptive Orientation of Multifunctional Nanowires for Magnetic Control of Bioelectrocatalytic Processes (pages 1508–1511)

      Óscar A. Loaiza, Rawiwan Laocharoensuk, Jared Burdick, Marcella C. Rodríguez, Jose M. Pingarron, Maria Pedrero and Joseph Wang

      Article first published online: 10 JAN 2007 | DOI: 10.1002/anie.200604082

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      Charging ahead: Adaptive functional nanowires can be used for magnetoswitchable bioelectrocatalysis. This control is accomplished by changing the surface orientation of two-segment gold/nickel nanowires, which are functionalized with glucose oxidase (GOx), in connection to a surface-bound ferrocene (Fc) electron-transfer mediator (see picture).

    26. Synthetic Study Towards Azadirachtin: An Efficient and Stereoselective Construction of the AB Rings with Full Functionality (pages 1512–1516)

      Hidenori Watanabe, Naoki Mori, Daisuke Itoh, Takeshi Kitahara and Kenji Mori

      Article first published online: 17 JAN 2007 | DOI: 10.1002/anie.200604097

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      From A to B: The decalin moiety of azadirachtin, which includes the fully functionalized AB ring system (see picture), was synthesized stereoselectively in only 23 steps. Key steps include an intramolecular Diels–Alder reaction, a decarboxylation, a Claisen rearrangement, and finally a tandem radical cyclization.

    27. Asymmetric Total Synthesis of (−)-Cribrostatin 4 (Renieramycin H) (pages 1517–1520)

      Guillaume Vincent and Robert M. Williams

      Article first published online: 19 JAN 2007 | DOI: 10.1002/anie.200604126

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      Out of the blue: The convergent asymmetric total synthesis of the antitumor antibiotic (−)-cribrostatin 4 from the blue sponge Cribrochalina features asymmetric Staudinger and Pictet–Spengler reactions to form the tetrahydroisoquinoline moiety. These reactions were followed by a reductive opening/elimination of a tricyclic β-lactam and a Pictet–Spengler cyclization to access the unsaturated pentacyclic core.

      Corrected by:

      Corrigendum: Corrigendum: Asymmetric Total Synthesis of (−)-Cribrostatin 4 (Renieramycin H)

      Vol. 50, Issue 37, 8458, Article first published online: 1 SEP 2011

    28. Cross-Linked Layered Structure of Magnetically Ordered [Fe(TCNE)2]⋅z CH2Cl2 Determined by Rietveld Refinement of Synchrotron Powder Diffraction Data (pages 1521–1524)

      Jae-Hyuk Her, Peter W. Stephens, Konstantin I. Pokhodnya, Michael Bonner and Joel S. Miller

      Article first published online: 26 JAN 2007 | DOI: 10.1002/anie.200604164

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      The wages of spin: Insight into the elusive structure of [V(TCNE)x]-based magnets is provided by the structural analysis of the title compound (Tc≈100 K; TCNE=tetracyanoethylene; z≈0.3), in which {FeII4-[TCNE]).−} layers are bridged by diamagnetic TCNE dimers μ4-[C4(CN)8]2− (see picture; Fe gold; C black; N blue). Strong intralayer spin coupling between the FeII centers leads to the observed magnetic ordering.

    29. Single-Crystal Organic Microtubes with a Rectangular Cross Section (pages 1525–1528)

      Xiujuan Zhang, Xiaohong Zhang, Wensheng Shi, Xiangmin Meng, Chunsing Lee and Shuittong Lee

      Article first published online: 16 JAN 2007 | DOI: 10.1002/anie.200604359

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      A simple solution process without the assistance of surfactant, catalyst, or template under ambient conditions in air has been used to prepare single-crystal hollow microtubes with a rectangular cross section from [2-(p-dimethylaminophenyl)ethenyl]phenylmethylenepropanedinitrile (DAPMP). The DAPMP microtubes (see picture for SEM images) show remarkably strong frequency-doubling nonlinear optical properties.

    30. The Azaallylic Anion as a Synthon for Pd-Catalyzed Synthesis of Heterocycles: Domino Two- and Three-Component Synthesis of Indoles (pages 1529–1532)

      José Barluenga, Agustín Jiménez-Aquino, Carlos Valdés and Fernando Aznar

      Article first published online: 16 JAN 2007 | DOI: 10.1002/anie.200604407

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      Piecing it all together with palladium: Two- and three-component cascade processes that are promoted by a multifunctional Pd catalyst lead to indoles in a highly efficient manner (see scheme). The key step is the Pd-catalyzed α-arylation of imines with o-dihalobenzene derivatives.

    31. Total Synthesis of (+)-Aquaticol by Biomimetic Phenol Dearomatization: Double Diastereofacial Differentiation in the Diels–Alder Dimerization of Orthoquinols with a C2-Symmetric Transition State (pages 1533–1535)

      Julien Gagnepain, Frédéric Castet and Stéphane Quideau

      Article first published online: 16 JAN 2007 | DOI: 10.1002/anie.200604610

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      Double or nothing: The bissesquiterpene (+)-aquaticol was synthesized by biomimetic oxidative dearomatization of 1 via an orthoquinol intermediate that undergoes spontaneous and selective dimerization; only like diastereomers react. The remarkable double diastereofacial differentiation observed is explained in terms of a double hyperconjugative “Cieplak–Fallis” effect expressed in a C2-symmetric bispericyclic transition state.

    32. Catalysis by Gold(I) and Gold(III): A Parallelism between Homo- and Heterogeneous Catalysts for Copper-Free Sonogashira Cross-Coupling Reactions (pages 1536–1538)

      Camino González-Arellano, Alberto Abad, Avelino Corma, Hermenegildo García, Marta Iglesias and Félix Sánchez

      Article first published online: 17 JAN 2007 | DOI: 10.1002/anie.200604746

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      Zero, one, or three? The role of Au0, AuI, and AuIII cations in the heterogeneous gold catalyst Au/CeO2 was investigated with the copper-free Sonogashira cross-coupling reaction of iodobenzene and phenyl acetylene (see picture). Reactions carried out under both heterogeneous and homogeneous conditions using distinct Au0, AuI, and AuIII species reveal that AuI is the active species for the cross-coupling reaction.

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      Preview: Angew. Chem. Int. Ed. 10/2007 (page 1543)

      Article first published online: 9 FEB 2007 | DOI: 10.1002/anie.200790030

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