Angewandte Chemie International Edition

Cover image for Vol. 45 Issue 36

September 11, 2006

Volume 45, Issue 36

Pages 5895–6061

  1. Cover Picture

    1. Top of page
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    3. Graphical Abstract
    4. Web Site
    5. Book Review
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    7. Review
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    1. Cover Picture: The First Structural Characterization of a Binary P–N Molecule: The Highly Energetic Compound P3N21 (Angew. Chem. Int. Ed. 36/2006) (page 5895)

      Michael Göbel, Konstantin Karaghiosoff and Thomas M. Klapötke

      Version of Record online: 5 SEP 2006 | DOI: 10.1002/anie.200690122

      A binary P–N molecule was unambiguously characterized for the first time. The cover shows the molecular structure of P3N21 determined by X-ray diffraction. The explosive decomposition of a sample in a drop-hammer experiment and the protective clothing that must be worn during such an experiment are also depicted. Further details on the balancing act between the formation and decomposition of this molecule are provided by T. M. Klapötke and co-workers in their Communication on page 6037 ff.

  2. Graphical Abstract

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    5. Book Review
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  3. Web Site

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    1. Lipids and Lipidomics (pages 5910–5911)

      Thomas Kolter

      Version of Record online: 5 SEP 2006 | DOI: 10.1002/anie.200603313

  4. Book Review

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    5. Book Review
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    7. Review
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  5. Highlights

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    1. A New Dimension in Multinuclear Metallocene Complexes (pages 5916–5918)

      Matthias Wagner

      Version of Record online: 14 AUG 2006 | DOI: 10.1002/anie.200601787

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      Radial oligocyclopentadienyl metal complexes were synthesized for the first time by a highly efficient Negishi coupling. Such compounds open fascinating possibilities for applications on the threshold between homogeneous and heterogeneous catalysis as well as in molecular electronics.

    2. Enzyme-Catalyzed Sulfide Ring Formation in Lantibiotics (pages 5919–5921)

      Günther Jung

      Version of Record online: 17 AUG 2006 | DOI: 10.1002/anie.200601850

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      Building bridges: The crystal structure of the zinc enzyme NisC was solved recently by X-ray diffraction. This cyclase single-handedly catalyzes the formation of several sulfide bridges in the dehydrated precursor protein NisA of the lantibiotic nisin. The Highlight discusses the impact of these results on the field of lantibiotic research.

  6. Review

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    1. The Supramolecular Chemistry of Organic–Inorganic Hybrid Materials (pages 5924–5948)

      Ana B. Descalzo, Ramón Martínez-Máñez, Félix Sancenón, Katrin Hoffmann and Knut Rurack

      Version of Record online: 5 SEP 2006 | DOI: 10.1002/anie.200600734

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      Taking chemical functionality to a new level: Blending 2D and 3D nanoscopic structures with supramolecular concepts can be used to generate systems for enhanced recognition and sensing, to control assembly and disassembly processes, and give the possibility for biomimetic reactions within nanoscopic scaffolds.

  7. Communications

    1. Top of page
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    4. Web Site
    5. Book Review
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    1. Simplified Analysis of Mixtures of Small Molecules by Chromatographic NMR Spectroscopy (pages 5950–5953)

      Guilhem Pages, Corinne Delaurent and Stefano Caldarelli

      Version of Record online: 26 JUL 2006 | DOI: 10.1002/anie.200601622

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      Break it up: Ordinarily, silica gel produces no separation in a mixture of aromatic molecules by HPLC; however, solid-enhanced DOSY NMR spectroscopy succeeds in this task, although its separation capabilities concern just the spectral components. Chromatographic NMR spectroscopy may thus prove a simple complement to HPLC in favorable cases. MAS=magic-angle spinning.

    2. Synthesis and Structure of the “Dialuminyne” Na2[Ar′AlAlAr′] and Na2[(Ar′′Al)3]: Al[BOND]Al Bonding in Al2Na2 and Al3Na2 Clusters (pages 5953–5956)

      Robert J. Wright, Marcin Brynda and Philip P. Power

      Version of Record online: 9 AUG 2006 | DOI: 10.1002/anie.200601925

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      An alkyne analogue with Al: The first “dialuminyne” of formula Na2[Ar′AlAlAr′] (see picture; Ar′=C6H3-2,6-(C6H3-2,6-iPr2)2) was synthesized and characterized by X-ray crystallography. The structure contains a planar trans-bent C–Al–Al–C array with an Al[BOND]Al bond length of 2.428(1) Å and a bending angle of 131.71(7)° at Al.

    3. Photochemical Upconversion: Anthracene Dimerization Sensitized to Visible Light by a RuII Chromophore (pages 5957–5959)

      Radiy R. Islangulov and Felix N. Castellano

      Version of Record online: 14 AUG 2006 | DOI: 10.1002/anie.200601615

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      Double up: Photochemical upconversion by MLCT-sensitized triplet–triplet annihilation is demonstrated (MLCT=metal-to-ligand charge transfer). Selective visible excitation of [Ru(dmb)3]2+ (dmb=4,4′-dimethyl-2,2′-bipyridine) in the presence of anthracene efficiently produces the [4+4] cycloaddition product. This transformation traditionally requires ultraviolet light.

    4. Proton-Fueled, Reversible Assembly of Gold Nanoparticles by Controlled Triplex Formation (pages 5960–5963)

      Young Hwan Jung, Kyung-Bok Lee, Yang-Gyun Kim and Insung S. Choi

      Version of Record online: 4 AUG 2006 | DOI: 10.1002/anie.200601089

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      Fueled up: The protonation of the imino group of cytosines in double-stranded DNA, which is required for the formation of a triplex, can be used to guide the assembly/disassembly of DNA-conjugated gold nanoparticles. The reversible switching of the nanoparticles is demonstrated by repeated cycling of pH between 5.0 and 6.5 with the proton as a fuel (see picture).

    5. Manganese Oxide Nanoparticles Electrodeposited on Platinum Are Superior to Platinum for Oxygen Reduction (pages 5963–5966)

      Mohamed S. El-Deab and Takeo Ohsaka

      Version of Record online: 4 AUG 2006 | DOI: 10.1002/anie.200600692

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      A change in orientation of adsorbed oxygen molecules from parallel (top) at the bare Pt electrode to a mixture of parallel and end-on modes at a Pt surface modified by the electrodeposition of manganese oxide nanoparticles (nano-MnOx/Pt) causes a higher population of oxygen molecules at the MnOx/Pt surface (bottom). The modified electrode is thus a superior electrocatalyst for the reduction of oxygen (Pt yellow, O white, MnOx black).

    6. Luminescence Studies of the Intracellular Distribution of a Dinuclear Gold(I) N-Heterocyclic Carbene Complex (pages 5966–5970)

      Peter J. Barnard, Louise E. Wedlock, Murray V. Baker, Susan J. Berners-Price, David A. Joyce, Brian W. Skelton and James H. Steer

      Version of Record online: 10 AUG 2006 | DOI: 10.1002/anie.200601526

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      Gold lights the way: A bidentate cyclophane N-heterocyclic carbene ligand has been used to synthesize a new dinuclear AuI complex of the formula [Au2L2]2+. The short Au⋅⋅⋅Au distance imposed by the rigid cyclophane ligand leads to a red-shifted luminescence profile that enables the complex to be used as a luminescent probe for distribution studies in single living cancer cells.

    7. Metal-Compound-Induced Vesicles as Efficient Directors for Rapid Synthesis of Hollow Alloy Spheres (pages 5971–5974)

      Xuanjun Zhang and Dan Li

      Version of Record online: 9 AUG 2006 | DOI: 10.1002/anie.200601617

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      Hollow alloy: Vesicles formed from tetrabutylammonium bromide and metal compounds act as efficient directors for the rapid synthesis of a variety of binary, ternary, and quaternary intermetallic materials with hollow structures. In this way, different metals were co-alloyed on the vesicle surface to produce hollow alloy spheres containing more than two kinds of metals.

    8. Metal–Organic Frameworks as Efficient Materials for Drug Delivery (pages 5974–5978)

      Patricia Horcajada, Christian Serre, María Vallet-Regí, Muriel Sebban, Francis Taulelle and Gérard Férey

      Version of Record online: 9 AUG 2006 | DOI: 10.1002/anie.200601878

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      Fill 'em up: The metal carboxylates MIL-100 and MIL-101 act as porous matrices (see picture; MIL=Materials of Institut Lavoisier) for drug-delivery systems using Ibuprofen as a model substrate. Very large amounts of the drug could be incorporated, up to an unprecedented capacity of 1.4 g of drug per gram of porous solid for MIL-101, and the total release of Ibuprofen was achieved under physiological conditions in 3 (MIL-100) and 6 days (MIL-101).

    9. Direct Monitoring of the Asymmetric Induction of Solid-Phase Catalysis Using Circular Dichroism: Diamine–CuI-Catalyzed Asymmetric Henry Reaction (pages 5978–5981)

      Takayoshi Arai, Masahiko Watanabe, Akitsugu Fujiwara, Naota Yokoyama and Akira Yanagisawa

      Version of Record online: 9 AUG 2006 | DOI: 10.1002/anie.200602255

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      The direct approach: A new high-throughput screening system for analyzing the asymmetric induction in catalytic enantioselective synthesis couples solid-phase reactions with a circular dichroism detection system (see picture). Thus, direct monitoring of asymmetric induction without the need for purification or chromatographic analysis is obtained.

    10. Auxetics at the Molecular Level: A Negative Poisson's Ratio in Molecular Rods (pages 5981–5983)

      Nir Pour, Lior Itzhaki, Benaya Hoz, Eli Altus, Harold Basch and Shmaryahu Hoz

      Version of Record online: 14 AUG 2006 | DOI: 10.1002/anie.200601764

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      Negative feedback: Auxetic materials are materials that, counterintuitively, become thicker when stretched and thinner when compressed (negative Poisson's ratio). Quantum mechanical computations were used to identify poly[n]prismanes (n=3–6), the first nanomolecular systems that manifest auxetic behavior at the molecular level. The magnitude of the negative Poisson's ratio in these prismanes ranges from 7 to 15 %.

    11. Highly Efficient Asymmetric Michael Addition of Aldehydes to Nitroalkenes Catalyzed by a Simple trans-4-Hydroxyprolylamide (pages 5984–5987)

      Claudio Palomo, Silvia Vera, Antonia Mielgo and Enrique Gómez-Bengoa

      Version of Record online: 4 AUG 2006 | DOI: 10.1002/anie.200602207

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      Discriminating reactions: While no self-aldol reaction is observed in the reaction shown, catalyst 1 promotes the Michael addition of aldehydes to nitroalkenes with the lowest catalyst loading and lowest stoichiometric ratio of reactant aldehyde that have been reported so far for this type of reaction.

    12. Activation of Aryl Germanium(II) Chlorides by [Mo(PMe3)6] and [W(η2-CH2PMe2)H(PMe3)4]: A New Route to Metal–Germanium Triple Bonds (pages 5987–5991)

      Alexander C. Filippou, Nils Weidemann, Athanassios I. Philippopoulos and Gregor Schnakenburg

      Version of Record online: 22 AUG 2006 | DOI: 10.1002/anie.200602061

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      A new activation mode of aryl germanium(II) chlorides at electron-rich metal centers leads to compounds featuring metal–germanium triple bonds. Reaction of 1 with RGeCl affords the hydrido–germylidene complex 2, which rearranges thermally to give the germylidyne complex 3 (see scheme; Trip=C6H2-2,4,6-iPr3). In contrast, the reaction of [Mo(PMe3)6] with RGeCl yields directly the germylidyne complex trans-[Cl(PMe3)4Mo[TRIPLE BOND]GeR].

    13. Gold(I)-Catalyzed Cyclizations of Silyl Enol Ethers: Application to the Synthesis of (+)-Lycopladine A (pages 5991–5994)

      Steven T. Staben, Joshua J. Kennedy-Smith, David Huang, Britton K. Corkey, Rebecca L. LaLonde and F. Dean Toste

      Version of Record online: 4 AUG 2006 | DOI: 10.1002/anie.200602035

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      In control: Gold(I)-catalyzed intramolecular addition of silyl enol ethers to alkynes and allenes allows for the diastereoselective synthesis of cyclopentenes with control of the position of the double bond. The utility of these reactions is demonstrated by an efficient total synthesis of (+)-lycopladine A that takes advantage of the orthogonal reactivity of AuI and Pd0 towards unsaturated iodides (see scheme).

    14. β-Disubstituted Allylic Chlorides: Substrates for the Cu-Catalyzed Asymmetric SN2′ Reaction (pages 5995–5998)

      Caroline A. Falciola, Karine Tissot-Croset and Alexandre Alexakis

      Version of Record online: 4 AUG 2006 | DOI: 10.1002/anie.200601855

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      Scope broadened: A previously developed asymmetric Cu-catalyzed allylic substitution can be applied to more substituted allylic patterns. Two classes of β-disubstituted substrates, cinnamyl derivatives and aliphatic endocyclic allylic chlorides, afford excellent regio- and enantioselectivities (see schemes; L*=phosphoramidite ligand).

    15. Self-Regenerating Rh- and Pt-Based Perovskite Catalysts for Automotive-Emissions Control (pages 5998–6002)

      Hirohisa Tanaka, Masashi Taniguchi, Mari Uenishi, Nobuhiko Kajita, Isao Tan, Yasuo Nishihata, Jun'ichiro Mizuki, Keiichi Narita, Mareo Kimura and Kimiyoshi Kaneko

      Version of Record online: 14 AUG 2006 | DOI: 10.1002/anie.200503938

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      As good as new: Perovskite-based catalysts containing Rh and Pt for use in exhaust-emissions control systems are developed. These catalysts are found to be self-regenerating and could thus lead to the use of lower amounts of precious metals. The picture shows the TEM image of Pt grains of catalyst CaTi0.95Pt0.05O3 aged in an engine exhaust at 900 °C for 100 h.

    16. Pd(OAc)2-Catalyzed Coupling/Cyclization of 2,3-Allenoic Acids and Methyl Propiolate: Observation of Double 1,7-Hydrogen Shifts (pages 6002–6005)

      Zhenhua Gu and Shengming Ma

      Version of Record online: 9 AUG 2006 | DOI: 10.1002/anie.200601699

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      On the move: A Pd(OAc)2-catalyzed coupling/cyclization reaction of 2,3-allenoic acids with methyl propiolate in the presence of [Sc(OTf)3]/BF3⋅Et2O (OTf=triflate) leads to a “π-bond migration” in the 1:2 adducts, which may proceed through double 1,7-hydrogen migrations.

    17. Storing and Releasing Hydrogen with a Redox Switch (pages 6005–6008)

      Simon K. Brayshaw, Jennifer C. Green, Nilay Hazari, J. Scott McIndoe, Frank Marken, Paul R. Raithby and Andrew S. Weller

      Version of Record online: 4 AUG 2006 | DOI: 10.1002/anie.200601434

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      Give and take: A molecular cluster that readily takes up and stores two molecules of H2 also rapidly releases (milliseconds) the stored H2 by a simple redox process. This process represents a new method of hydrogen storage and release from a well-defined molecular material.

    18. Metallic Magnesium Nano/Mesoscale Structures: Their Shape-Controlled Preparation and Mg/Air Battery Applications (pages 6009–6012)

      Weiyang Li, Chunsheng Li, Chunyuan Zhou, Hua Ma and Jun Chen

      Version of Record online: 4 AUG 2006 | DOI: 10.1002/anie.200600099

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      Magnesium nano/mesostructures with spherical, platelike, rodlike, and sea-urchin-like shapes are prepared by a simple and efficient vapor-transport method. They exhibit excellent electrochemical properties in Mg/air batteries. The figure shows discharge curves of the Mg/air batteries made from two samples, at a constant current of 0.5 mA and a temperature of 25 °C.

    19. Solid-State Phase Transition of an Inclusion Complex of 5-Methyl-2-pyridone with 1,3,5-Benzenetricarboxylic Acid (pages 6013–6016)

      Shinya Hirano, Shinji Toyota, Fumio Toda, Kotaro Fujii and Hidehiro Uekuasa

      Version of Record online: 9 AUG 2006 | DOI: 10.1002/anie.200600845

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      Changed in a flash: A photochemically unreactive crystal of 5-methyl-2-pyridone with a trimesic acid host is transformed in the solid state into a reactive phase by heating or by contact with solvent vapor. The mechanism was revealed to involve desolvation and a 180° turn of one molecule with respect to the other.

      Corrected by:

      Corrigendum: Solid-State Phase Transition of an Inclusion Complex of 5-Methyl-2-pyridone with 1,3,5-Benzenetricarboxylic Acid

      Vol. 46, Issue 4, 486, Version of Record online: 10 JAN 2007

    20. Anomeric Acetates of N-Acetylneuraminic Acid are Useful C-Sialyl Donors in Samarium-Mediated Reformatsky Coupling Reactions (pages 6016–6020)

      Adeline Malapelle, Zouleika Abdallah, Gilles Doisneau and Jean-Marie Beau

      Version of Record online: 9 AUG 2006 | DOI: 10.1002/anie.200601209

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      Teaching an old molecule new tricks: A new solution for an expeditious C-sialylation from N-acetylneuraminic acid involves the use of the peracetylated derivative 1, a very common starting material prepared 40 years ago in Heidelberg, through an anomeric umpolung by samarium diiodide without an additive, in the presence of a carbonyl compound. Excellent yields are obtained for the coupling with cyclic ketones (see scheme).

    21. N-Heterocyclic Carbene Catalyzed C[BOND]C Bond Cleavage in Redox Esterifications of Chiral Formylcyclopropanes (pages 6021–6024)

      Stephanie S. Sohn and Jeffrey W. Bode

      Version of Record online: 26 JUL 2006 | DOI: 10.1002/anie.200601919

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      A clean break: An N-heterocyclic carbene catalyzes the ring-opening of chiral non-racemic formylcyclopropanes, with simultaneous oxidation of the aldehyde function and without the need for stoichiometric reagents. The activated carboxylate intermediate is trapped by a variety of nucleophiles, thus leading to chiral esters, thioesters, or carboxylic acids (see scheme; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene, EWG=electron- withdrawing group, Nu=nucleophile.)

    22. Enantioselective Catalytic Intramolecular Cyclopropanation using Modified Cinchona Alkaloid Organocatalysts (pages 6024–6028)

      Carin C. C. Johansson, Nadine Bremeyer, Steven V. Ley, Dafydd R. Owen, Stephen C. Smith and Matthew J. Gaunt

      Version of Record online: 4 AUG 2006 | DOI: 10.1002/anie.200602129

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      A mechanism-guided design process was used to develop cinchona alkaloids that are substituted at the C2′ position of the quinoline moiety. These compounds prove to be excellent organocatalysts for an enantioselective intramolecular cyclopropanation reaction (see scheme).

    23. Gold(I)-Catalyzed Intermolecular Cyclopropanation of Enynes with Alkenes: Trapping of Two Different Gold Carbenes (pages 6029–6032)

      Salomé López, Elena Herrero-Gómez, Patricia Pérez-Galán, Cristina Nieto-Oberhuber and Antonio M. Echavarren

      Version of Record online: 10 AUG 2006 | DOI: 10.1002/anie.200602448

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      Caught in a trap: Intermolecular cyclopropanation reactions of enynes with alkenes allows the synthesis of complex cyclic systems with gold(I) catalysts under mild conditions. Furthermore, gold carbenes are trapped intermolecularly with alkenes (see scheme; L=ligand), thereby providing experimental evidence for the involvement of two different types of metal carbenes in the skeletal rearrangement of enynes.

    24. Property-Oriented Rational Design of Single-Molecule Magnets: A C3-Symmetric Mn6Cr Complex based on Three Molecular Building Blocks with a Spin Ground State of St=21/2 (pages 6033–6037)

      Thorsten Glaser, Maik Heidemeier, Thomas Weyhermüller, Rolf-Dieter Hoffmann, Holger Rupp and Paul Müller

      Version of Record online: 9 AUG 2006 | DOI: 10.1002/anie.200600712

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      Forced to comply: The MnIII6CrIII complex 1 is constructed from two trinuclear manganese triplesalen complexes and one [Cr(CN6)]3− ion, and possesses a spin ground state of St=21/2. The threefold symmetry enforced by the triplesalen ligand precludes a complete cancellation of the single-site magnetic anisotropies and minimizes quantum tunneling of the magnetization. The analysis of the magnetic properties reveals that this complex is indeed a single-molecule magnet.

    25. The First Structural Characterization of a Binary P–N Molecule: The Highly Energetic Compound P3N21 (pages 6037–6040)

      Michael Göbel, Konstantin Karaghiosoff and Thomas M. Klapötke

      Version of Record online: 29 AUG 2006 | DOI: 10.1002/anie.200601670

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      An explosive mixture: The first structural characterization of a binary molecule of phosphorus and nitrogen is described. With the help of a new synthetic strategy, the phosphorus azide P3N21 is prepared in pure form, and single crystals are isolated, enabling a structure determination by X-ray diffraction (see structure; P orange, N blue).

    26. Efficient Synthesis of Functionalized Organozinc Compounds by the Direct Insertion of Zinc into Organic Iodides and Bromides (pages 6040–6044)

      Arkady Krasovskiy, Vladimir Malakhov, Andrei Gavryushin and Paul Knochel

      Version of Record online: 10 AUG 2006 | DOI: 10.1002/anie.200601450

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      Insider dealing: A wide range of polyfunctional (hetero)aromatic and aliphatic zinc reagents can be easily prepared in THF. The compounds are formed by a Zn insertion reaction mediated by the addition of LiCl (see scheme; All=allyl).

    27. Mechanistic Studies of Catalytic Polyethylene Chain Growth in the Presence of Water (pages 6044–6046)

      Andreas Berkefeld and Stefan Mecking

      Version of Record online: 9 AUG 2006 | DOI: 10.1002/anie.200601387

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      Position blocked? Quantitative studies of polyethylene chain growth in the presence of water by variable-temperature (VT) 1H NMR spectroscopy show, unexpectedly, that water can compete with monomer binding at the vacant coordination site in cationic diimine palladium(II) methyl as well as higher alkyl complexes (see scheme); the latter are prepared cleanly as water complexes at T<0 °C.

    28. 18F-Labeling of Peptides by means of an Organosilicon-Based Fluoride Acceptor (pages 6047–6050)

      Ralf Schirrmacher, Gerrit Bradtmöller, Esther Schirrmacher, Oliver Thews, Julia Tillmanns, Thomas Siessmeier, Hans G. Buchholz, Peter Bartenstein, Björn Wängler, Christof M. Niemeyer and Klaus Jurkschat

      Version of Record online: 3 AUG 2006 | DOI: 10.1002/anie.200600795

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      F on: Fluorotriorganosilyl-derivatized Tyr3-octreotate was labeled with 18F providing the first practical formulation in 18F-radiochemistry for the labeling of a peptide (see scheme). The very mild reaction conditions and the fast labeling make this strategy a valuable tool for the synthesis of 18F-radiopharmaceuticals.

    29. Li26 Clusters in the Compound Li13Na29Ba19 (pages 6051–6053)

      Volodymyr Smetana, Volodymyr Babizhetskyy, Grigori V. Vajenine and Arndt Simon

      Version of Record online: 9 AUG 2006 | DOI: 10.1002/anie.200602137

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      A star is born: The Li26 cluster in the new intermetallic phase Li13Na29Ba19 can be described on the basis of a tetrahedral star (left) or four interpenetrating centered icosahedra (right). The M26 cluster is known from γ-brass and was predicted to be stable for Li in the gas phase. Li13Na29Ba19 contains the first example of a homoatomic M26 cluster in the solid state.

    30. Regioselective Iron-Catalyzed Allylic Amination (pages 6053–6056)

      Bernd Plietker

      Version of Record online: 9 AUG 2006 | DOI: 10.1002/anie.200602261

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      Iron age: An air- and water-resistant iron(−II) catalyst, in the presence of triphenylphosphane under buffered conditions, allows for the highly regioselective and stereoselective allylation of primary aromatic amines. A broad substrate range both in the aniline and in the allyl carbonate moiety is tolerated.

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