Angewandte Chemie International Edition in English

Cover image for Vol. 29 Issue 5

May 1990

Volume 29, Issue 5

Pages 439–564

Currently known as: Angewandte Chemie International Edition

    1. Cover Picture (Angew. Chem. Int. Ed. Engl. 5/1990)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199004391

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      The cover illustration shows, in the middle, a table containing the apparatus used by Otto Hahn, Lise Meitner, and Fritz Strassmann in their search for transuranium elements in uranium samples that had been subjected to neutron irradiation: counting tubes and the associated amplifiers for detecting radioactivity, the counters themselves, and power supplies (left and center); neutron sources (background right) and equipment for chemical isolation of the resulting active species (foreground right); and the historic laboratory notebook. It was with these materials that Otto Hahn and Fritz Strtassmann were occupied when they established the presence of radioactive barium in the radiochemical “indicator experiment” on December 17, 1938, an experiment in which uranium nuclei were split into nuclei corresponding to two elements of intermediate mass. Günter Herrmann discusses these historic experiments from the years 1934--1939 in the article beginning on page 481. The fission product barium would today be identified at a glance from its γ-spectrum (shown at the bottom of the illustration), which reveals characteristic γ-lines for three barium isotopes. One of these is barium-139, half-life 83 min, the isotope with which the indicator experiment was actually performed. In the background is depicted a modern apparatus for radiochemical separation, fully automated and computer controlled. Photographs: A. Zschau, GSI Darmstadt, and Deutsches Museum, Munich.

    2. Graphical Abstract (Angew. Chem. Int. Ed. Engl. 5/1990)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199004392

  1. Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    1. Two-Dimensional Model Networks (pages 439–448)

      Dr. Heinz Rehage and Prof. Dr. Madeleine Veyssié

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199004393

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      Ultrathin membranes are extremely interesting model systems, for example in the investigation of complex biological processes. One can thus study the deformation of oil droplets under flow conditions as a function of the elasticity of the surrounding membrane (see illustration on the right; the arrow indicates the flow direction). An important potential application is diagnosis through simple viscosity measurements of blood diseases derived from abnormal changes in the membrane flexibility of erythrocytes.

    2. Boron-Phosphorus Compounds and Multiple Bonding (pages 449–460)

      Prof. Philip P. Power

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199004491

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      The length of the bond between boron and phosphorus, and thus the extent of multiple bonding, is strongly dependent upon what substituents are present. Species with highly reactive P-B multiple bonds are stabilized by bulky substituents. Acyclic and cyclic B-P π systems may thus be formed. For example, the structure data for 1 (R1 = 2,4,6-(CH3)3C6H2; R2 = cyclo-C6H11) unequivocally show that the B3P3 ring is a benzene analogue.

    3. The Chemistry of Vitamin A and Vision (pages 461–480)

      Prof. Robert R. Rando

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199004611

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      The physical phenomenon of light and the biological processes known as sight are linked by the chemistry of the visual cycle. The current interpretation of this process is indicated below, in schematic form. A key piece of evidence is the recent discovery that the energy required for reconstituting 11-cis-retinol is supplied by phospholipids in the pigment epithelial membrane.

    4. Five Decades Ago: From the “Transuranics” to Nuclear Fission (pages 481–508)

      Prof. Dr. Günter Herrmann

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199004811

      “The history of nuclear fission”, writes G. Herrmann, “tells us of how science often evolves, not by successive logical steps but rather through strange detours; how for many years the most experienced groups miss the central point in their experiments and in their thinking because they remain attached to seemingly well-founded but erroneous concepts; how in the end they intuitively find the right track; and how after decades a scientist returns to the kind of work he pursued as a beginner.”

  2. Communications

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    1. Kinetic Isotope Effects as a Mechanistic Tool for the Elucidation of the Rate-Determining Step(s) in the Transition-Metal-Ion-Mediated Activation of CH/CC Bonds. Ethylene Loss from Metastable 4-Octyne/M Complexes in the Gas Phase (pages 509–510)

      Prof. Dr. Christian Schulze and Dr. Helmut Schwarz

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005091

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      The nature of the transition-metal ion M determines which of the steps (CH activation or loss of olefin) will be rate-determining in the regiospecific formation of ethylene from 4-octyne: with M = Cr or Cu it is CH activation, but with M = Fe it is the loss of ethylene. Both steps are subject to isotope effects, with M = Cr or Ni.

    2. Rhodium-Catalyzed Synthesis of Trisubstituted Olefins from Ethene Derivatives and Diazoalkanes (pages 510–512)

      Dr. Justin Wolf, Lutz Brandt, Arno Fries and Prof. Dr. Helmut Werner

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005101

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      Synthesis of square-planar carbene complexes was the goal, but a novel catalytic olefin synthesis was the result. A mixture of diphenyldiazomethane and its derivatives 1 with ethene, propene, or styrene provided, in the presence of catalytic amounts of [{RhCl(C2H4)2}2], a good yield of the olefins 2, with turnover numbers as high as 500 (R [DOUBLE BOND] H, Me, Ph; R′ [DOUBLE BOND] H, Me, Cl, etc.).

    3. Enantioselective Catalysis with a New Zirconium Trichloride Lewis Acid Containing a “Dibornacyclopentadienyl” Ligand (pages 512–514)

      Prof. Dr. Gerhard Erker and Dr. Adolphus. A. H. van der Zeijden

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005121

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      ee Values in excess of 80% can be achieved in C[BOND]C coupling reactions of 1-naphthol with pyruvate esters using the chiral Lewis acid 1 as catalyst. Complex 1 is available from (+)-camphor via a five-step synthesis with an overall yield of ca. 30%.

    4. What Are the Structures of Fenestin A and Fenestin B? (pages 514–515)

      Prof. Dr. Ulrich Schmidt, Dr. Albrecht Lieberknecht, Dr. Uli Kazmaier and Prof. Dr. Ernst Haslinger

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005141

      1H NMR signals at unusually high field (δ = 3.9–4.1 rather than 4.0–4.6 as in known cyclopeptides) render the proposed structures 1 and 2 unlikely for fenestin A and fenestin B, two cyclopeptides isolated from Pacific sponges. Synthesis and analysis of the postulated compound 2 as well as the dimer of 1 have made it possible to show that the suggested structure for fenestin B is wrong, while that for fenestin A must at least be regarded as questionable.

      • equation image
    5. 5-Methyl-1,1,3,3-tetraphenyl-1λ5, 3λ5- diphosphabenzene (pages 516–517)

      Prof. Dr. Hubert Schmidbaur, Dipl.-Chem. Christos Paschalidis, Dipl.-Chem. Oliver Steigelmann and Priv.-Doz. Dr. Gerhard Müller

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005161

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      “Regions of conjugation” rather than an aromatic system as in 4′ characterize the title compound 4, easily prepared from the ethylene derivative 1 by way of 2 and 3. The nearly planar 4 consists of a methallyl anion attached to a diphenylphosphoniomethanide cation.

    6. Unraveling Overlapping Multiplets in Two-Dimensional NMR Correlation Spectra by Selective Inversion of Coupling Partners (pages 517–520)

      Lyndon Emsley, Peter Huber and Prof. Dr. Geoffrey Bodenhausen

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005171

      Clean and simple two-dimensional multiplet pallerns instead of overlapping multiplets can be generated in an NMR experiment by employing selective pulses that single out small segments of a complete spectrum. The pattern of the selected multiplet is in this case manipulated by altering the apparent signs of the coupling constants. The technique is suitable not only for separating overlapping signals, but also for testing hypotheses associated with particular coupling networks.

    7. Synthesis of (±)-Phyllanthocin via a Metal-Catalyzed Cycloreduction (pages 520–522)

      Professor Barry M. Trost and Dr. Eric D. Edstrom

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005201

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      Cycloreduction of the enyne 2 to a precursor of the title compound 1 is the key step in a total synthesis of 1. The reaction occurs under Pd catalysis with a yield of 86%. This is a case in which the Alder ene reaction proved unsuccessful. Compound 1 is the aglycone of the clinically interesting antitumor agent phyllanthoside (TIPS = iPr3Si).

    8. Bis(N,N-diisopropylamino)trimethylsiloxy-phosphane: A Novel Flexible Phosphitylating Reagent in Nucleoside Chemistry and Its Application in the Synthesis of P-Modified Nucleotides (pages 522–523)

      Dr. Wojciech Da̧bkowski, Prof. Dr. Jan Michalski and Wang Qing

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005221

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      Dinucleotides such as 3, with reactive groups on phosphorus, can be readily prepared starting with the title compound 1. The first step is.conversion of 1 into the silylphosphites 2, compounds whose synthetic potential has certainly not yet been exhausted.

    9. Catalytic Hydration of Acrylonitrile to Acrylamide under Mild Conditions (pages 523–525)

      Prof. Jik Chin and J. H. Kim

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005231

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      Intramolecular attack of a hydroxyl group on a coordinated nitrile is the key step in the CoIII-catalyzed hydrolysis of nitriles to amides. The CoIII catalyst is highly selective; for example, the double bond of acrylonitrile remains intact during the hydrolysis.

    10. Oligorylene as a Model for “Poly(perinaphthalene)” (pages 525–527)

      Dipl.-Chem. Angelika Bohnen, Dipl.-Chem. Karl-Heinz Koch, Prof. Dr. Wolfgang Lüttke and Prof. Dr. Klaus Müllen

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005251

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      Rylenes are annelated arenes derived formally by coupling all the peri-positions of naphthalene. Several soluble oligorylenes have now been synthesized as models for “polyrylene” 1. R = H. Among the most striking features to emerge in the course of characterizing the compounds were a small HOMO/ LUMO energy gap for the quaterrylene 2, R = tBu, n = 2. and a high powder conductivity for the charge-transfer complex of the same compound.

    11. Synthesis of Enantiomerically Pure Heterosteroids by Intramolecular Hetero-Diels-Alder Reaction (pages 527–529)

      Prof. Dr. Lutz F. Tietze, Dr. Uwe Beifuss, Dr. Magdolna Lökös, Dipl.-Chem. Matthias Rischer, Dipl.-Chem. Axel Göhrt and Prof. Dr. George M. Scheldrick

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005271

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      A tandem Knoevenagel/hetero-Diels–Alder reaction of the aldehyde 2 with the cyclic 1,3-dioxo compound 1 and its analogues leads stereoselectively to the trans-bonded heterosteroids 3 (de > 98%). Aldehyde 2 is obtained by ozonolysis of enantiomerically pure tetrahydroindanone derivatives, which are in turn readily available by the Wiechert-Hajos procedure.

    12. Synthesis of the First Silaamidide (pages 529–530)

      Dr. Gail E. Underiner and Prof. Robert West

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005291

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      A 1,3-diaza-2-silaallyl anion characterizes the salts 2 and 3, in which the Li counterion is either coordinated to Et2O or remains in a free state. Compound 2 was prepared from the silanediamine 1 by straightforward metalation, and then isolated as a colorless solid. Attempts at X-ray structure analysis were unsuccessful, but the structure was nonetheless firmly established through a series of chemical transformations.

    13. A Facile Synthesis of β-Selenolactams (pages 530–531)

      Dr. Hideharu Ishihara, Michinari Yoshimi and Prof. Dr. Shinzi Kato

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005301

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      The cis β-selenolactams 1 have been obtained in 70–89% yield by reaction (a). The only exception encountered was the amine in which R1 = 4-CH3C6H4, R2 = i-C3H7 a compound that led to a mixture of cis (59%) and trans (10%) isomers. R1 = C6H5, 4-CH3C6H4; R2 = C6H5, i-C3H7, 4-CH3C6H4,C6H5CH2, 4-ClC6H4.

    14. ZnIIFeIII and FeIIFeIII Complexes Containing a Novel (μ-Phenoxo)bis(μ-diphenylphosphato)-dimetal(II,III) Core as Model Complexes for Active Sites of Purple Phosphatases (pages 531–533)

      Dipl.-Chem. Klaus Schepers, Dipl.-Chem. Bernd Bremer, Prof. Dr. Bernt Krebs, Prof. Dr. Gerald Henkel, Dipl.-Chem. Erika Althaus, Dr. Bernd Mosel and Prof. Dr. Werner Müller-Warmuth

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005311

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      What is the mechanism of action of the purple phosphatases? It is known that these important enzymes contain bimetallic centers with mixed valences (e.g., ZnIIFeIII or FeIIFeIII) as well as coordinated phosphate. The title compounds are model complexes with two phosphate and one heptadentate (6 N, 1 O) bridging ligands. The model complexes and the enzyme compare quite favorably in several respects. • (left) = Fe; • (right) = Zn; equation image

    15. A New Route to 1,3-Diphospholide Ions. Synthesis and X-Ray Structure Analysis of a 1,3-Diphosphaferrocene (pages 534–535)

      Dr. Nicole Maigrot, Dr. Louis Ricard, Dr. Claude Charrier and Prof. François Mathey

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005341

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      New perspectives are opened by the synthesis of 1,3-diphospholide ions such as 2 from 1,2-diphosphetenes like 1. The Ph substituents of 2 are easily varied by choosing an appropriately substituted starting material; even the H atom in 2 is subject to replacement. Compound 2 reacts with a cationic cyclopentadienyliron species to give the corresponding terrocene analogue.

    16. Clays Direct Aromatic Nitration (pages 535–536)

      Christine Collet, Dr. Alfred Delville and Prof. Dr. Pierre Laszlo

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005351

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      The influence of kaolinite on the nitration of 1 appears not to involve intercalation: the increase from 1% to 27% in the yield of 3 at the expense of 2 during nitration in the presence of a solid support is instead a consequence of the fact that the CO leaving group is protonated as it is adsorbed onto the strongly acidic surface of the clay mineral. This in turn leads to considerable stabilization of the reaction intermediate.

    17. Formation of an Aminoreductone from Glucose (pages 536–537)

      Sabine Estendorfer, Prof. Dr. Franz Ledl and Prof. Dr. Theodor Severin

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005361

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      Nonenzymatic browning of foods (the Maillard reaction) is frequently observed when reducing sugars react with proteins or amino acids in the presence of heat. It has now been shown that, at temperatures as low as 37 °C, glucose reacts with propylamine via the Amadori product to give the title compound 1 in 0.1% yield.

    18. Atomic Structure and Superstructure of α-RuCl3 by Scanning Tunneling Microscopy (pages 537–541)

      Prof. Dr. Hans-Joachim Cantow, Dipl.-Chem. Harald Hillebrecht, Dr. Sergej N. Magonov, Dr. Heinz Wilhelm Rotter, Dipl.-Phys. Markus Drechsler and Prof. Dr. Gerhard Thiele

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005371

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      Three-dimensional distortion is apparent in the hexagonal arrangement of the surface Cl atoms in crystalline αRuCl3, as revealed by scanning tunneling microscopy. A hexagonal superlattice is clearly apparent at room temperature (see illustration at right; open and filled circles, Cl; triangles, Ru). The observed distortion is probably a consequence of weak interactions between paired Ru atoms immediately below the crystalline surface.

    19. Stability and Cyclization of Enol Radical Cations: A Mechanistic Study of One-Electron Oxidation of β,β-Dimesityl Enols (pages 541–543)

      Dr. Michael Schmittel and Dipl.-Chem. Ulrich Baumann

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005411

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      A reversal in the position of the keto/enol equilibrium through one-electron oxidationa —a phenomenon already observed in the gas phase—has now also been verified in solution. The ΔG° values (1˙⊕ [RIGHTWARDS ARROW] 2˙⊕) for the two enols 1 (R = tBu, H) are −17.7 and −25.7 kcal mol−1. Benzofurans 2 are obtained as reaction products from the radical cations in over 80% yield.

    20. Synthesis and Structure of Annelated Carbon Rings Containing a Bridgehead Transition Metal (pages 543–545)

      Professor Joseph M. O'Connor, Lin Pu and Dr. Raj Chadha

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005431

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      An iridium atom in a bridgehead position is the most unusual feature of 2, which was obtained in place of the anticipated carbene vinylidene complex upon reaction of 1 with propiolic acid. Equally surprising is the fact that 2 must be regarded as an oxonium system rather than as a carbene, the most obvious resonance alternative. R [DOUBLE BOND] CO2CH3.

    21. A Borate Propeller Compound as Chiral Catalyst for an Asymmetrically Induced Diels-Alder Reaction (pages 545–546)

      Priv.-Doz. Dr. Dieter Kaufmann and Dr. Roland Boese

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005451

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      Three binaphthyl groups as “blades” have been joined together to give the propeller compound 1. The synthesis of this compound proved surprisingly easy via reaction of a borane with optically active 1,1′-bi-2-naphthol. Compound 1 is more than just “a cute molecule”; it also catalyzes a highly exo and enantioselective Diels–Alder reaction of cyclopentadiene with methacrolein.

    22. Fast Heteronuclear 3D NMR Spectroscopy (pages 546–548)

      Dipl.-Chem. Peter Schmieder, Prof. Dr. Horst Kessler and Dr. Hartmut Oschkinat

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005461

      Carbon atom correlations become interesting in 3D NMR spectroscopy if one selects CH2 groups with an inverse DEPT sequence in such a way that the spectral breadth in two of the dimensions is limited. 3 D DEPT-TOCSY has made it possible to obtain, within about ten hours and with a very good signal-to-noise ratio, a high-resolution 13C-resolved 3D NMR spectrum of a cyclic hexapeptide.

    23. Synthesis and 2D-(1H,103Rh)-NMR Study of the First “Non-Classical” Polyhydrido Complex Stabilized by a Nitrogen Donor Ligand (pages 548–549)

      Dipl.-Chem. Urs E. Bucher, Dipl.-Chem. Thomas Lengweiler, Dipl.-Chem. Daniel Nanz, Prof. Dr. Wolfgang von Philipsborn and Prof. Dr. Luigi M. Venazi

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005481

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      The H2 ligand in 1 is stabilized only by nitrogen ligands. 1H-Detecting 2D-(1H,103Rh)-NMR spectroscopy, an NMR procedure in the preliminary phase of which a heteronuclear two-spin coherence is excited, together with variation of the 1H-transmitter frequency, made it possible to read directly from the spectrum both the chemical shift of the metal and the number of hydride ligands present.

    24. On the Way to Ligating Oligocyclopentadienyls: Synthesis and Preliminary Reactions of the Two Isomeric Tercyclopentadienyls and Their Transition Metal Complexes (pages 549–552)

      Dr. Roland Boese, Randy L. Myrabo, Dr. David A. Newman and Prof. Dr. K. Peter C. Vollhardt

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005491

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      Homo- and heterotrinuclear transition-metal complexes of the two tercyclopentadienyl isomers have now become accessible via a generalizable synthetic strategy. The tricyclic ligands are prepared by coupling the fulvalene dianion with 3-chloro-2-cyclopentenone. Such transition-metal complexes—with or without M-M bonds—permit intramolecular transfer of the ligands L between the various metal atoms.

    25. Solid-State NMR Studies of the Structure and Reactivity of Metakaolinite (pages 553–554)

      Dr. João Rocha and Jacek Klinowski

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005531

      Si atoms in various environments, as well as tetra-, penta-, and hexacoordinated AI atoms, have been observed in metakaolinite by high-resolution solid-state NMR spectroscopy. Their ratios depend upon the calcination temperature. Studies have shown that the most reactive metakaolinite (calcination temperature 480-500 °C) is associated with a minimum concentration of hexacoordinate and a maximum concentration of tetra- and pentacoordinate Al.

    26. New Chiral Auxiliaries for Enolate Alkylations (pages 555–556)

      Kyu-Sung Jeong, Kevin Parris, Pablo Ballester and Prof. Dr. Julius Rebek Jr.

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005551

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      The stereospecific synthesis (>99:1) of α-alkylcarboxylic acids 3 has been achieved using chiral auxiliaries such as 1, which is a derivative of the Kemp triacid. Compound 1 is coupled at the imide group with the acid chloride 2. Lithiation ([RIGHTWARDS ARROW]enolate), alkylation, and cleavage leads to 3. The effectiveness of 1 is a consequence of the fact that it shields one side of the enolate from attack by the electrophile EX (examples: R [DOUBLE BOND] Me, E [DOUBLE BOND] PhCH2, or R [DOUBLE BOND] PhCH2, E [DOUBLE BOND] Me).

    27. 1-Amino- and 1,3-Diaminoimidazolium Salts (pages 556–557)

      Dr. Helmut Link, Prof. Dr. Wilhelm Klötzer, Dr. Eva Maria Karpitschka, Dr. Marc Montavon, Dr. Renate Müssner and Dr. Nicolas Singewald

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005561

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      A high activity against filaria is demonstrated by l,3-bis[p-aminobenzyl-(idene)amino]imidazolium salts such as 2. Synthesis of 2 involves amination of 2-phenylimidazole with o-(diphenylphosphinoyl)hydroxylamine (DPH) and condensation of the 1,3-diamino product 1 with p-dimethylaminobenzaldehyde. Derivatives of 2 that are unsymmetrically substituted and/or aminated in position 2 are also accessible.

    28. Novel Diphosphinoiridium Catalysts for the Enantioselective Hydrogenation of N-Arylketimines (pages 558–559)

      Dr. Felix Spindler, Dr. Benoit Pugin and Dr. Hans-Ulrich Blaser

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005581

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      Optical yields as high as 84% ee and turnover numbers up to 10000 are achievable when a catalyst system consisting of [Ir(C8H12)Cl]2, a chiral diphtisphino compound, and iodide is used in the enantioselective hydrogenation of N-arylketimines 1. The anti/syn ratio of the imines has no influence on the selectivity of the hydrogenation.

  3. Book Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    1. Book Review: Colloid Chemistry of Polymers. By Y. S. Lipatov (pages 563–564)

      Heinz Hoffmann

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199005632

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