Angewandte Chemie International Edition in English

Cover image for Vol. 34 Issue 1

January 16, 1995

Volume 34, Issue 1

Pages 3–122

Currently known as: Angewandte Chemie International Edition

    1. Cover Picture (Angew. Chem. Int. Ed. Engl. 1/1995)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500011

      Thumbnail image of graphical abstract

      The cover picture shows the environment of the Rb-centered Rb6 octahedron in the compound Na16Rb7Sb7 (Na = anthracite. Rb = blue, Sb = red). The virtually spherical isosurfaces of the partial electron densities are colored according to the values of the electron localization function (high values are white). They support the interpretation of the Rb-centered Rb6 octahedron as Rb (Rb+)6. More about this unusual antimonide that was prepared from the elements under inert conditions at 873 K is reported by H. G. von Schnering et al. on page 103ff.

  1. Reviews

    1. Top of page
    2. Reviews
    3. Highlights
    4. Communications
    5. Book Reviews
    1. Organometallic Compounds for Nonlinear Optics—The Search for En-light-enment! (pages 21–38)

      Dr. Nicholas J. Long

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500211

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      With the rapid development of opto-electronic technology, new materials are required that show nonlinear optical phenomena and at the same time fulfill a series of additional criteria such as optical transparency, thermal stability, processability, and ease of application-specific modification. Organometallic systems, like 1, through their unique characteristics such as diversity of metals, oxidation states, ligands, and geometries, allow fine-tuning of the properties to be carried out, which thus makes them suitable candidates for device application.

    2. Toxins as Tools in Neurochemistry (pages 39–50)

      Prof. Dr. Ferdinand Hucho

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500391

      The extremely different structures and properties of the neurotoxins enable them to interact very specifically with key sites in the nervous system. Neurochemists are beginning to deduce the site of action from the neurotoxin structure. These compounds have already proved invaluable in detecting and analyzing the key sites, for example, in the conduction of nerve impulses within neurons and in their transfer from cell to cell.

  2. Highlights

    1. Top of page
    2. Reviews
    3. Highlights
    4. Communications
    5. Book Reviews
    1. New Findings in the Electrophilic Addition of Halogens to Olefins (pages 51–53)

      Priv.-Doz. Dr. Rainer Herges

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500511

      Electrophilic addition—so you thought you knew it all! Recent research into the title reaction shows that a reexamination of well-established mechanisms by means of modern theoretical, analytica, and synthetic methods can be altogether worthwhile. For example. A. C. Legon et. al (Angew. Chem. Int. Ed. Engl.1994, 33, 1512–1513) recently investigated the interactions between ethene and halogens with an FT microwave spectrometer equipped with a fast-mixing nozzle.

    2. Mononuclear Tris(arene)–Metal Complexes (pages 53–54)

      Prof. Dr. Ulrich Zenneck

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500531

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      The reaction of arene anions with metal halides is not only an elegant approach to arenemetalates, but may also lead to structurally novel complexes, as Ellis et al. recently found (Angew. Chem. Int. Ed. Engl.1994, 33, 1973–1975) in, for instance, the potassium salt of 1, the first tris(arene)metal complex with three independent arene ligands.

  3. Communications

    1. Top of page
    2. Reviews
    3. Highlights
    4. Communications
    5. Book Reviews
    1. Structure Determination from Powder X-Ray Diffraction Data of a Hydrogen-Bonded Molecular Solid with Competing Ferromagnetic and Antiferromagnetic Interactions: The 2-(3,4-Dihydroxyphenyl)-α-Nitronyl Nitroxide Radical (pages 55–57)

      Joan Cirujeda, Luis Enrique Ochando, Prof. Jose Maria Amigó, Dr. Concepció Rovira, Dr. Jordi Rius and Dr. Jaume Veciana

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500551

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      A Single crystal was not needed for the structure determination of radical 1. This is the first time that structure of a purely organic molecule having only s and p electrons and with more than ten atoms the unit cell was obtained from powder X-ray diffraction data. The structure is in agreement with expected from the magnetic properties of 1.

    2. Barbituric Acid/2,4,6-Triaminopyrimidine Aggregates in Water and Their Competitive Interaction with a Monolayer of Barbituric Acid Lipids at the Gas–Water Interface (pages 58–60)

      Dr. Thomas M. Bohanon, Steffen Denzinger, Ralf Fink, Dr. Wolfgang Paulus, Prof. Dr. Helmut Ringsdorf and Marcus Weck

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500581

      The first synthetic model for competitive exchange of an organic compound, specifically the exchange of triaminopyrimidine (TAP) between barbituric acid/TAP aggregates in water and highly ordered monolayers of a barbituric acid lipid, were studied by IR and UV/Vis spectroscopy. Similar competitive interaction are important in membranes and cell biology.

    3. A Versatile Solid-Phase Synthesis of N-Linked Glycopeptides (pages 60–63)

      Dr. Dirk Vetter, Dr. David Tumelty, Dr. Sunil K. Singh and Dr. Mark A. Gallop

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500601

      A convergent synthesis not requiring sugar protecting groups yields N-glycopeptides. The key step is the condensation of unprotected glycosylamines with resin-bound peptides that have activated carboxyl groups in specified positions. Twenty-three N-linked glycopeptides such as 1 and 2 all derived from one peptide motif were obtained. This approach should facilitate generation of glycopeptide libraries.

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    4. A New Zincosilicate Zeolite with Nine-Ring Channels (pages 63–65)

      Dipl.-Min. Carsten Röhrig and Prof. Dr. Hermann Gies

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500631

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      The spiro-5 building block 1 is an unusual arrangement of five [TO4] tetrahedra (T [DOUBLE BOND] Si, Zn) to give two three-rings of tetrahedra. This building unit is the backbone of the partial structure of the tetrahedral framework of the new zincosilicate zeolite 2. The nonframework components Na+, K+, and H2O likewise form a three-dimensional network, which contributes considerably to the stability of 2.

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    5. Molecular Recognition of Anions by Zwitterionic Host Molecules in Water (pages 65–66)

      Dr. Karin Worm and Prof. Dr. Franz P. Schmidtchen

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500651

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      Up to now cationic hosts were necessary for the molecular recognition of hydrophilic anions in water. This task can, however, also be performed with the cage molecule 1 having zero net charge. The vital design feature is the rigid separation of substructures of unlike charge, which enables encapsulation of the guest in the central cavity.

    6. Thermal Isomerization of Indigo (pages 67–68)

      Doz. Dr. Günter Haucke and Dr. Gerhard Graness

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500671

      Thumbnail image of graphical abstract

      At about 460°C indigo (1) isomerizes to dibenzonaphthyridindione (2) in the gas phase remarkably smoothly with ring enlargement to incorporate the central C[BOND]C double bond. The transition state was calculated (PM3) and is characterized by the rupture of the bonds between the carbonyl groups and the central C[DOUBLE BOND]C unit.

    7. The Novel Copper Polytelluride Salts NaBa6Cu3Te14 and (K0.60Ba0.40)Ba6Cu2.58Te14: Discrete Clusters or Extended Solids? (pages 68–71)

      Dr. Xiang Zhang, Jon L. Schindler, Tim Hogan, Joyce Albritton-Thomas, Dr. Carl R. Kannewurf and Prof. Dr. Mercouri G. Kanatzidis

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500681

      Thumbnail image of graphical abstract

      Columnar stacks of discrete Cu3Te3 six-membered rings in which each copper atom is also coordinated to a Temath image chelating ligand are present in the crystals of 1 (depicted on the right) and in the isomorphous compound 2. The stacks are held together by Te…Te interactions; sodium ions are located in interstitial sites between the rings, and Ba2+ and Te2− ions cocrystallize for charge neutralization. Compounds 1 and 2 are semiconductors with a narrow band gap.

      • equation image
    8. Na2Ti3Cl8: From Isolated Ti2+ Ions to [Ti3]6+ Clusters (pages 71–73)

      Dr. Dirk J. Hinz, Prof. Dr. Gerd Meyer, Dipl.-Chem. Thorsten Dedecke and Prof. Dr. Werner Urland

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500711

      Thumbnail image of graphical abstract

      Na2Ti3Cl8 is a temperature-dependent magnetic switch. The switching process (= phase transition) takes places below room temperature and is accompanied by a drastic decrease in magnetic susceptibility and molar volume. The transition is attributed to the formation of [Ti3]6+ clusters (see diagram) by two-dimensional Peierl's distortion within math image[TiCl4/2Cl2/3]2− layers.

    9. Homogeneous versus Heterogeneous Zeolite Nucleation (pages 73–75)

      Dr. Ir. Wim H. Dokter, Drs. Harold F. van Garderen, Dr. Ir. Theo P. M. Beelen, Prof. Dr. Rutger A. van Santen and Drs. Wim Bras

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500731

      Thumbnail image of graphical abstract

      Aggregates of fractal dimension were found in the intermediate gel phases that organize prior to nucleation and crystallization (shown right) of silicalite from a homogeneous reaction mixture. Small- and wide-angle X-ray scattering studies prove that for zeolites nucleation may be homogeneous or heterogeneous.

    10. Orthorhombic and Monoclinic 2,3,7,8-Tetramethoxythianthrene: Small Structural Difference–Large Lattice Change (pages 76–78)

      Prof. Dr. Hans Bock, Dipl.-Chem. Andreas Rauschenbach, Dipl.-Chem. Christian Näther, Dr. Zdenek Havlas, Prof. Dr. Angelo Gavezzotti and Dr. Guiseppe Filippini

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500761

      Thumbnail image of graphical abstract

      Merely the change of the solvent for the crystallization of the title compound leads to different crystal modifications. In the orthorhombic crystals (from n-hexane) a methoxy group is twisted out of the C6 plane (see structure). In the monoclinic crystals (from diisopropyl ether) all four methoxy groups lie in the plane of the C6 rings.

    11. (S)-(+)- and (R)-(–)-1,5-Dimethyl-4-phenyl-1,5-dihydro-2H-pyrrol-2-ones by Carbene Ring Contraction and Decarboxylation of (2 R, 3 S)-(–)- and (2 S, 3 R)-(+)-6-Diazo-3,4-dimethyl-2-phenyloxazepane-5,7-diones (pages 78–79)

      Dr. Giorgio Chelucci and Prof. Dr. Antonio Saba

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500781

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      Catalytic decomposition of diazo compound 1, which is readily available in homochiral form, leads exclusively to the unsaturated, enantiomerically pure lactam 2. This chiral C5-building block and its enantiomer open access to asymmetric pyrrolidinones and pyrrolidines, which are of potential therapeutic utility.

    12. Elusiveness of CuIII Complexation; Preference for Trifluoromethyl Oxidation in the Formation of [CuI(CF3)4] Salts (pages 80–81)

      Prof. Dr. James P. Snyder

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500801

      Thumbnail image of graphical abstract

      Where are the electrons in copper complexes with a formal CuIII oxidation state? Ab initio calculations suggest cuprate 1 to contain a d10 Cu1 metal atom and the average of one CFmath image and three CFmath image groups. Assignment of oxidation numbers based on consideration of the metal center alone can be misleading.

    13. 1,3,5,7-Tetraphosphabarrelene: A New Cyclic Phosphaalkyne Tetramer (pages 81–83)

      Prof. Dr. Paul Binger, Dr. Gerald Glaser, Barbara Gabor and Dr. Richard Mynott

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500811

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      A surprisingly straightforward cyclotetramerization of tBuC ≡ P in the coordination sphere of an η8-cyclooctatertraene–zirconium complex yields 1,3,5,7-tetraphosphabarrelen 1. The bicyclic compound is initially bound to the Zr atom through two P[DOUBLE BOND]C bonds, but can easily be liberated from the complex by reaction with hexachloroethane.

    14. Oligomethylene-Bridged Vitamin B12 Dimers (pages 84–86)

      Prof. Dr. Bernhard Kräutler, Dipl.-Ing. Tomas Dérer, Dr. Pingli Liu, Mag. Walter Mühlecker, Dr. Michael Puchberger, Mag. Karl Gruber and Prof. Dr. Christoph Kratky

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500841

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      The reaction of the highly nucleophilic CoI form of vitamin B12 with 1,ω-dibromo-n-alkanes (ω ≥ 4) leads to oligomethylene-bridged B12 dimers in high yields. Use of 1,4-dibromobutane results in a dimer (shown schematically on the right), in which the two cobalamin moieties are tightly packed and coaxially linked through a tetramethylene chain, which is a synclinal conformation.

    15. A Highly Symmetric Sixfold Cycloaddition Product of Fullerene C60 (pages 87–88)

      Prof. Dr. Bernhard Kräutler and Mag. Josef Maynollo

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500871

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      In one step and with 26% yield, a sixfold Diels-Alder product is formed from buckminsterfullerene C60 and 2,3-dimethyl-1,3-butadiene. This first direct synthesis of a highly symmetric, exohedrally sixfold substituted fullerene addition product is remarkably simple. The components were heated in ortho-dichlorobenzene at roughly 110°C for ten days, and the product was purified by column chromatography.

    16. Photoswitchable Phase Separation in Hydrophobically Modified Poly(acrylamide)/Surfactant Systems (pages 88–90)

      Dr. Jochem J. Effing and Prof. Dr. Jan C. T. Kwak

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500881

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      Through light-induced cis–trans isomerization of the hydrophobic azobenzene fragment (see below), the binding of surfactant molecules to hydrophobically modified poly(acrylamide)s can be switched on and off, which influences phase separation and gel formation.

    17. Micron-Scale Patterning of Biological Molecules (pages 91–93)

      David John Pritchard, Dr. Hywel Morgan and Dr. Jonathan Mark Cooper

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500911

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      Site-specific attachment of biological molecules on gold and silicon dioxide surfaces has been achieved: The surface is modified with the receptor/ligand pair avidin D/photobiotin 1 and exposed to light through a mask in the presence of a protein solution; binding only occurs in the exposed areas. After unbound material is removed by washing, this process can be repeated several times to produce a two-dimensional pattern. One of the potential applications of this technique is the patterning of antibodies in a format that can be used in a multi-analyte immunosensor.

    18. The Structural and Thermodynamic Basis for the Formation of Self-Assembled Peptide Nanotubes (pages 93–95)

      Prof. M. Reza Ghadiri, Dr. Kenji Kobayashi, Dr. Juan R. Granja, Dr. Raj K. Chadha and Dr. Duncan E. McRee

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500931

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      Nanostructures through self-assembly: Suitably designed planar cyclic peptides like 1 form cylindrical dimers in nonpolar organic solvents. These ensembles are good models for the fundamental description of parallel and antiparallel β-sheet structures as well as for the design of novel peptide nanostructures. The analysis of the structural and thermodynamic aspects of the dimerization process showed that the hydrogen bonds between the peptide backbones are crucial factors for the stability of the ensembles and selective formation of β-sheet arrangements. Furthermore 1 crystallizes to form a novel, porous, solid-state object with an amphiphilic tubular superlattice, which may have potential utility in the molecular inclusion of hydrophilic and hydrophobic substrates.

    19. β-Sheet Peptide Architecture: Measuring the Relative Stability of Parallel vs. Antiparallel β-Sheets (pages 95–98)

      Dr. Kenji Kobayashi, Dr. Juan R. Granja and Prof. M. Reza Ghadiri

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500951

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      Nanostructures through self-assembly: Suitably designed planar cyclic peptides like 1 form cylindrical dimers in nonpolar organic solvents. These ensembles are good models for the fundamental description of parallel and antiparallel β-sheet structures as well as for the design of novel peptide nanostructures. The analysis of the structural and thermodynamic aspects of the dimerization process showed that the hydrogen bonds between the peptide backbones are crucial factors for the stability of the ensembles and selective formation of β-sheet arrangements. Furthermore 1 crystallizes to form a novel, porous, solid-state object with an amphiphilic tubular superlattice, which may have potential utility in the molecular inclusion of hydrophilic and hydrophobic substrates.

    20. Synthesis and Structure of a Dendritic Polysilane (pages 98–99)

      Prof. Joseph B. Lambert, Jodi L. Pflug and Charlotte L. Stern

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199500981

      The first dendritic polysilane, methyl[tris(permethylneopentasilyl)]silane [(Me3Si)3-SiSiMe2]3SiMe, has been synthesized starting from (Me3Si)3SiH and characterized by crystallography. The dendrimer comprises 27 Si7 pathways and consequently exhibits UV absorption with greatly enhanced intensity over that of simple linear polysilanes of similar length.

    21. Isolation and X-Ray Crystal Structure of a Palladacyclobutane: Insight into the Mechanism of Cyclopropanation (pages 100–102)

      Prof. H. M. R. Hoffmann, Dr. Andreas R. Otte, Dr. Andreas Wilde, Dr. Stephan Menzer and Dr. David J. Williams

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199501001

      Thumbnail image of graphical abstract

      The intermediate metallacycle 1 was isolated from the reaction of the corresponding (η3-allyl)-palladium complex with deprotonated isobutyronitrile in THF/TMEDA (TMEDA = N,N,N′,N′-tetramethylethylenediamine). When CO was passed over a solution of 1 in dichloromethane at room temperature, the compound underwent spontaneous, stereoselective reductive elimination to form the corresponding cyclopropane.

    22. The Stabilization of the Rb Ion in Na16Rb7Sb7 = Na16(RbRb6)Sb7 (pages 103–105)

      Prof. Dr. Hans Georg von Schnering, Dr. Raúl Hector Cardoso Gil, Dr. Wolfgang Hönle, Dr. Armin Burkhardt, Dr. Georges Krier and Prof. Ole Krogh Andersen

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199501031

      An unusual electron distribution is shown by the ternary antimonide Na16Rb7Sb7, since only 21 of the 23 valence electrons of the alkali metal atoms are required for the formation of the Sb3− centers to be expected because of the semiconducting behavior. The remaining two electrons are localized in the region of a Rb center, which is located inside a Rb6 octahedron. The formulation of this center as Rb is supported for example by the synthesis of the isostructural Na16Rb6ISb7 and by the results of quantum chemical calculations.

    23. The Colors of C60 Solutions (pages 105–107)

      Prof. Dr. Javier Catalán, Dr. José L. Saiz, Dr. José L. Laynez, Dr. Nadine Jagerovic and Dr. José Elguero

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199501051

      Differences in the absorption intensity in the spectral range between 400 and 500 nm, which the human eye perceives as changes in color, are the reason why solutions of C60 show different colors. The results of the experiments described rule out the formation of charge transfer complexes or of C60 aggregates.

    24. Photosensitized Formation of 8-Hydroxy-2′-deoxyguanosine in Salmon Testes DNA by Furocoumarin Hydroperoxides: A Novel, Intercalating “Photo-Fenton” Reagent for Oxidative DNA Damage (pages 107–110)

      Prof. Dr. Waldemar Adam, Dr. Jean Cadet, Prof. Dr. Francesco Dall'Acqua, Prof. Dr. Bernd Epe, Dr. Danaboyina Ramaiah and Dr. Chantu R. Saha-Möller

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199501071

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      Furocoumarin hydroperoxides such as 1 are novel photochemical sources of hydroxyl radicals; in salmon testes DNA they form the mutagenic oxidation product 8-hydroxy-2′-deoxyguanosine 2 in up to 1.8% yield on UVA irradiation (λ = 350 nm).

    25. Solid-State and Solution Structures of [{NW(OC(CH3)2CF3)3}3] and Factors Favoring the Metathesis of C[BOND]N and W[BOND]W Triple Bonds in Reactions Involving Organic Nitriles and Ditungsten Hexaalkoxides (pages 110–112)

      Prof. Malcolm H. Chisholm, Dr. Kirsten Folting-Streib, Darin B. Tiedtke, Frédéric Lemoigno and Prof. Odile Eisenstein

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199501101

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      A planar W3N3 ring showing marked alternation in the bond lengths (structures shown on the right) is the distinctive structural element in the trimeric tungsten nitride 1 (R = C(CH3)2CF3), which was obtained by reaction of the alkoxide [W2(OR)6] with benzonitrile. When R = SitBuMe2, a complex is formed in solution with a central W2O2 ring and terminal nitrio ligands.

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    26. Aggregation of Nitrido–Metal Complexes: The Example of [(η5-C5Me5)Mo(N)Cl2] (pages 112–115)

      Prof. Dr. Wolfgang A. Herrmann, Sandra Bogdanovic, Thomas Priermeier, Prof. Dr. Rinaldo Poli and Dr. James C. Fettinger

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199501121

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      The reactive nitridomolybdenum(VI) fragment 1 is available from the reaction of [Cpmath imageMo2Cl6] with azides. Aggregation occurs in different ways depending on the conditions to afford compounds containing six-membered rings with either localized or delocalized metal–nitrogen multiple bonds. The nature and structure of the products indicates that 1 has a nucleophilic nitrido ligand.

    27. An Ab Initio Investigation of the RhI-Catalyzed Hydroboration of C[DOUBLE BOND]C Bonds: Evidence for Hydrogen Migration in the Key Step (pages 115–118)

      Dr. Andrea E. Dorigo and Prof. Dr. Paul von Ragué Schleyer

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199501151

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      Participation of several 14-electron complexes as intermediates in the [Rh(PH3)3Cl]-catalyzed addition of BH3 to alkenes is suggested by results of ab initio pseudopotential computations, which also indicate a preference for migration of a hydrogen atom rather than the BH2 group to the C [DOUBLE BOND] C bond in the key step. The calculations also provide a rationale for the diastereoselectivity of the reaction. The structure calculated for one of the intermediates is shown on the right.

  4. Book Reviews

    1. Top of page
    2. Reviews
    3. Highlights
    4. Communications
    5. Book Reviews
    1. Book Review: FT-NIR Atlas. By M. Buback and H. P. Vögele (pages 120–121)

      Wolfram Sander

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199501201

    2. Book Review: Activated Metals in Organic Synthesis. By P. Cintas (page 121)

      Paul Knochel

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199501211

    3. Book Review: Cluster Chemistry. By G. González-Morega (pages 121–122)

      Lutz H. Gade

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199501212

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