Angewandte Chemie International Edition in English

Cover image for Vol. 17 Issue 1

January 1978

Volume 17, Issue 1

Pages 1–72

Currently known as: Angewandte Chemie International Edition

    1. Cover Picture (Angew. Chem. Int. Ed. Engl. 1/1978)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800011

    2. Graphical Abstract (Angew. Chem. Int. Ed. Engl. 1/1978)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800012

  1. Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Abstracts
    5. Book Reviews
    1. Chemical Oscillations (pages 1–15)

      Prof. Dr. Ulrich F. Franck

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800013

      Thumbnail image of graphical abstract

      Rhythmic chemical reactions (

      , flip-flop oscillation;

      , sawtooth oscillation) constitute interesting deviations from normal kinetics

      . They result from feedback, autocatalysis, and autoinhibition, etc.

    2. Industrial Applications of Photochemical Syntheses (pages 16–26)

      Dr. Martin Fischer

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800161

      Thumbnail image of graphical abstract

      Photonitrosation of cyclohexane is a recent example of an industrial photoreaction with stoichiometric light reqirements. Apart from the established radical chain reactions such as chlorination, sulfochlorination, sulfoxidation, and nitrosation, photochemical processes are being used on an increasing scale in the synthesis of vitamins, drugs, and fragrances.

    3. Organomercury Compounds in Organic Synthesis (pages 27–37)

      Prof. Richard C. Larock

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800271

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      Solvomercuration-demercuration and carbene transfer number among the principal reactions of organomercurials.

    4. Solid Ionic Conductors: Principles and Applications (pages 37–46)

      Prof. Dr. Hans Rickert

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800371

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      Doped ZrO2, β-Al2O3, AgI, CaF2, and numerous other inorganic solids transport electric current by means of their ions. The ionic conductivity can resemble that in molten salts. Solid-state ionic conductors are becoming increasingly important as components of fuel cells, batteries, sensors, etc.

  2. Communications

    1. Top of page
    2. Reviews
    3. Communications
    4. Abstracts
    5. Book Reviews
    1. Cyclophanes Having Orthogonal Benzene Rings (pages 46–47)

      Neil Jacobson and Prof. Dr. Virgil Boekelheide

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800461

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      The long-sought [2](4,4″)-orthoterphenylophane(2) has been prepared from (1), X = Br, with phenyllithium in ether. Particular interest attaches to such cyclophanes in which benzene rings are held orthogonal to each other.

    2. Synthesis of Disparlure by Kolbe Electrolysis (pages 47–48)

      Dipl.-Chem. Helmut Klünenberg and Prof. Dr. Hans J. Schäfer

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800471

      Thumbnail image of graphical abstract

      Disparlure(1), the sex attractant of the gypsy moth, has now been obtained in configurationally pure form by double Kolbe electrolysis. “Contamination” by geometrical isomers seriously impairs the attractant properties of synthetic pheromones.

    3. tert-Alkylation of Ketones and Aldehydes (pages 48–49)

      Doz. Dr. Manfred T. Reetz and Dipl.-Chem. Wilhelm F. Maier

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800481

      Thumbnail image of graphical abstract

      α-Alkylation of carbonyl compounds(1) via the corresponding base cannot be used for the introduction of tert-alkyl groups. This important C[DOUBLE BOND]C coupling reaction has now been accomplished by a route involving (2), which is allowed to react with tert-alkyl chloride in the presence of TiCl4, FeCl3, or ZnCl2.

    4. Effect of Shift Reagents on NMR Coupling Constants (pages 49–50)

      Dr. Geoffrey Brian Porter and Jon Simpson

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800491

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      Chelates formed from difunctional molecules (1) and NMR shift reagents (LSR) have now been detected for the first time by means of the coupling constants (J23). The J23 values were measured as a function of the LSR/(1) ratio and compared with calculated J23 values for three conformers of threo-and erythro-(1).

    5. Stretching Frequency and Force Constant of the Tungsten-Carbon Triple Bond (pages 50–51)

      Prof. Dr. Ernst Otto Fischer, Dr. Nguyen Quy Dao and Dipl.-Chem. Wolfgang Rainer Wagner

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800501

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      The IR and Raman spectra of the carbyne complexes(1) to (4) have been analyzed in order to gain a further insight into the nature of the metal-carbon bond. The results provide independent proof of a triple bond.

    6. Copolymerization of Tetrameric Thioformaldehyde with Oligomeric Thioformaldehydes, Substituted Analogs, or Sulfur (pages 51–52)

      Prof. Dr. Max Schmidt and Dr. Eckhard Weissflog

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800511

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      Polymethylene sulfides and related compounds possessing interesting properties are obtained when the highly reactive intermediate (2) (diradical or zwitterion?) arising from tetrameric thioformaldehyde (1) and boron trifluoride-diethyl ether is allowed to act upon trimeric thioformaldehyde, or substituted oligomeric thioformaldehyde, or even sulfur (S8).

    7. [Au2(WS4)2]2−, A Novel Inorganic Ring System (page 52)

      Prof. Dr. Achim Müller, Dipl.-Chem. Horst Dornfeld, Dr. Gerald Henkel, Prof. Dr. Bernt Krebs and Dr. M. P. A. Viegers

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800521

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      An eight-membered gold-sulfur-tungsten ring contains the anion of the salt [Ph4P]2[Au2(WS4)2]. It has now been prepared as dark red crystals from Na3[Au-(S2O32)]·2H2O, Ph4PBr, and (NH4)2WS4.

    8. Novel Method for the Detection of Indirectly Identifiable Photochemical Intermediates (pages 52–53)

      Univ.-Doz. Dr. Gerd Kaupp and Heinz-Willi Grüter

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800522

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      Mechanistic information about thermally supported photoreactions can be obtained by comparing the temperature dependence of fluorescence and quantum yield. These principles were demonstrated for the reaction (1) [RIGHTWARDS ARROW] (2), which proceeds via an intermediate—presumably (3)—when conducted at not too low a temperature.

    9. Selenium Dioxide Insertion into the Iron-Methyl Bond of η5-C5H5Fe(CO)2CH3 (pages 53–54)

      Dr. Ingo-Peter Lorenz

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800531

      The first seleninato complex to be obtained by SeO2 insertion is a brown solid that is stable for several days on exposure to air. It was characterized by its mass, 1H-NMR, and IR spectra (seleninato-Se type). SO2 insertions into transition metal-carbon bonds are known.

      • equation image
    10. L,L-3,6-[Methanothio(2,3-indolo)methano]piperazine-2,5-dione, the Smallest Phallotoxin Model (pages 54–55)

      Prof. Dr. Theodor Wieland, Priv.-Doz. Dr. Christian Birr and Dr. Giancarlo Zanotti

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800541

      Thumbnail image of graphical abstract

      The characteristic structural unit of the phallotoxins [e.g. phalloin (1)] from the green deathcap toadstool, the bridged cyclic dipeptide (2), has now been synthesized via the cyclic thioether. Compound (2) is nontoxic.

    11. Stable [2+2]-Cycloadducts of Ketones with Phosphazenes Having Five-Membered Rings (pages 55–56)

      Prof. Dr. Alfred Schmidpeter and Dipl.-Chem. Thomas von Criegern

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800551

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      The formal analogy between the Wittig reaction and the addition of ketones to compounds having P[DOUBLE BOND]N bonds includes the formation of an intermediate. The four-membered ring compound (1) is isolable owing to stabilization by the σ5-phosphorus atom.

    12. Synthesis of cyclo-Heptasulfur, S7, from S8 (pages 56–57)

      Prof. Dr. Ralf Steudel and Dipl.-Chem. Hans-Joachim Mäusle

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800561

      2 Million tonnes of cyclo-S7 exist in equilibrium in the 30 million tonnes of liquid sulfur produced annually throughout the world. It is now possible to extract cyclo-S7 from quenched melts on a preparative scale, thus making the species readily accessible.

    13. X-Ray Structure Analysis of cyclo-Decasulfur, S10 (pages 57–58)

      Dipl.-Chem. Richard Reinhardt, Prof. Dr. Ralf Steudel and Dipl.-Chem. Fritz Schuster

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800571

      Thumbnail image of graphical abstract

      The structure of cyclo-S10, a synthetic product, has been established by X-ray structure analysis on a single crystal. to a close approximation, cyclo-S10 possesses the very rare D2 symmetry.

    14. An Alkylsulfur Imide Amide (Methanesulfinamidine)—Relation between Coordination Number and Bond Length (pages 58–59)

      Prof. Dr. Herbert W. Roesky, Dipl.-Chem. Manfred Diehl, Prof. Dr. Hartmut Fuess and Dr. Jan Willem Bats

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800581

      Thumbnail image of graphical abstract

      The lengths of the four sulfur-nitrogen bonds in the alkylsulfur imide amide (1) can be correlated with the coordination numbers of the S and N atoms. The conventional formulation with S[BOND]N and S[DOUBLE BOND]N bonds is not very suitable for describing the bonding in the molecule.

    15. The First Reversible Thermal Dissociation of Distannanes, R3Sn—SnR3 (page 59)

      Dipl.-Chem. Hans U. Buschhaus and Prof. Dr. Wilhelm P. Neumann

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800591

      Thumbnail image of graphical abstract

      The reversible formation of stannyl radicals (2) from distannanes(1) bearing bulky substituents has now been demonstrated for the first time. (1a) begins to dissociate at ca. 180°C, and (1b) at ca. 100°C in solution.

    16. Bombykal, a Second Pheromone Component of the Silkworm Moth Bombyx mori L (page 60)

      Dr. Gerhard Kasang, Dr. Karl Ernst Kaissling, Dr. Otto Vostrowsky and Prof. Dr. Hans Jürgen Bestmann

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800601

      The chemical communication between the male and female silkworm moth is more complicated than hitherto assumed. The known attractant bombykol, an alcohol, acts on only one type of receptor cell in the male, whereas the female scent excites both kinds. Once it had been demonstrated that the corresponding synthetic aldehyde (bombykal) excites the other kind of receptor cells, this compound was sought and found in the abdominal glands of the female moth (ca. 15 ng per gland).

    17. Triptycenophanes—Synthesis via “Double Nonbenzylic Sulfone Pyrolysis” (pages 60–62)

      Prof. Dr. Fritz Vögtle and Dipl.-Chem. Philippe Koo Tze Mew

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800602

      Thumbnail image of graphical abstract

      The first 9,10-bridged triptycene(1), n = 12, is a remarkable model compound for stereochemical studies. In spite of unfavorable steric conditions, it can be synthesized by twofold ring contraction with C[BOND]C linkage.

    18. Quaternary Ammonium Salts as Catalysts of Nucleophilic Substitution Reactions in a Solid-Liquid Two-Phase System (pages 62–63)

      Dr. Andrzej Jończyk, Dipl.-Chem. Maria Ludwikow and Prof. Dr. Mieczyslaw Ma̧kosza

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800621

      Solid inorganic salts react with dissolved organic compounds if a lipophilic tetraalkyl-ammonium salt is added as catalyst, e.g. Aliquat 336® (technical grade methyl-trioctylammonium chloride). This catalyst is less expensive than crown ethers.

      • equation image
    19. Reactive Derivatives of Aliphatic N-Sulfinylamines—Alkylation of N-Sulfinylalkylamines and Bis (tert-butyl)-sulfur Diimide (page 63)

      Prof. Dr. Günter Kresze and Dipl.-Chem. Michael Rössert

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800631

      N-Sulfinylimmonium tetrafluoroborates (3) are valuable reagents and certainly not mere inorganic curiosities; they are readily accessible by alkylation of N-sulfinylamines (1). Former syntheses of similar salts were much more involved. The salts (3) are very good cycloaddition partners, and also provide a new entry to aminosulfonium salts of type (4).

      • equation image
      • equation image
    20. A New Synthetic Entry to Mono-, Bis-, and Tris-(amino)sulfonium Salts (page 64)

      Prof. Dr. Günter Kresze and Dipl.-Chem. Michael Rössert

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800641

      N-Sulfinylimmonium tetrafluoroborates (3) are valuable reagents and certainly not mere inorganic curiosities; they are readily accessible by alkylation of N-sulfinylamines (1). Former syntheses of similar salts were much more involved. The salts (3) are very good cycloaddition partners, and also provide a new entry to aminosulfonium salts of type (4).

      • equation image
      • equation image
    21. New Compounds from 1,4-Diaza-1,3-dienes and Iron Carbonyls: Hexacarbonyl(1,4-diazadiene)diiron and Substituted 2(3H)-Imidazolones (pages 64–65)

      Dr. Hans-Werner Frühauf, Armin Landers, Dr. Richard Goddard and Dr. Carl Krüger

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800642

      Thumbnail image of graphical abstract

      Novel dinuclear iron complexes containing unsymmetrically bonded 1,4-diaza-1,3-dienes (dad) are formed by the pathway sketched out below. Some dad ligands are transformed into imidazolones by insertion of CO, this reaction competing with the formation of (dad)Fe(CO)3.

    22. Reactivity of Alkenes in Free-Radical Additions (pages 66–67)

      Priv.-Doz. Dr. Bernd Giese and Dipl.-Chem. Wolfgang Zwick

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800661

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      The addition of alkyl radicals to alkenes is a reaction of considerable significance (polymerization of olefins). Competition experiments surprisingly show that methylmaleic anhydride (1b) reacts slower with nucleophilic alkyl radicals than the unsubstituted anhydride (1a). Hence radicals are not always stabilized by alkyl groups.

    23. Syntheses with 2-Phosphonioethoxycarbonyl Protecting Groups: Peptide Synthesis in Water (pages 67–68)

      Prof. Dr. Horst Kunz

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800671

      Thumbnail image of graphical abstract

      Peptide synthesis in homogeneous aqueous solution requires protecting groups which enhance the water-solubility of the protected amino acids and peptides. The Peoc groups (R1, R2, R3 = alkyl, aryl) have this property. They are extremely resistant to acids (CF3COOH!), but can be removed by weak bases.

    24. Tricyclic Isoindoles (pages 68–69)

      Prof. Dr. Richard Kreher and Dipl.-Ing. Karl Josef Herd

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800681

      Thumbnail image of graphical abstract

      Isoindoles with annelated rings, e.g. (1) and (2), X = SO2CH3, are remarkably stable compared to the parent compound. Tautomeric forms of (1) with benzenoid or quinonoid structure could not be detected.

    25. Molecular Structure of F5SOSF5, F5SeOSeF5, and F5TeOTeF5: d-Orbital Participation in Bonds between Main Group Elements (pages 69–70)

      Prof. Dr. Heinz Oberhammer and Priv.-Doz. Dr. Konrad Seppelt

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800691

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      Do d-orbitals participate in bonding between main group elements? Bond angles and bond lengths, and above all the eclipsed geometry of the fluorine atoms in the molecules (1) to (3) suggest that an additional (pd) π bond is superposed on the X[BOND]O bond. The chalcogen-fluorine bonds probably also contain a component of this kind.

  3. Abstracts

    1. Top of page
    2. Reviews
    3. Communications
    4. Abstracts
    5. Book Reviews
    1. ABSTRACTS (pages 70–71)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197800701

  4. Book Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Abstracts
    5. Book Reviews

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