Angewandte Chemie International Edition in English

Cover image for Vol. 17 Issue 3

March 1978

Volume 17, Issue 3

Pages 141–220

Currently known as: Angewandte Chemie International Edition

    1. Cover Picture (Angew. Chem. Int. Ed. Engl. 3/1978)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197801411

    2. Graphical Abstract (Angew. Chem. Int. Ed. Engl. 3/1978)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197801412

  1. Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Abstracts
    5. Book Reviews
    1. Nitrogen as Leaving Group: Dediazoniations of Aromatic Diazonium Ions (pages 141–150)

      Prof. Dr. Heinrich Zollinger

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197801413

      One of the best nucleofugic leaving groups is N2. Solvent is found to exert a mechanism-determining effect on thermal elimination of N2 from aromatic diazonium salts: whether the reaction follows a homolytic or a heterolytic course generally depends upon the specific solvation.

    2. Photochemical Rearrangements and Fragmentations of Alkenes and Polyenes (pages 150–168)

      Univ.-Doz. Dr. Gerd Kaupp

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197801501

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      Systematic analysis of the intramolecular reactions of electronically excited alkenes has shown that any choice between energetically feasible competing reactions is primarily determined by geometrical factors.

    3. Selective Reactions with Organoaluminum Compounds (pages 169–175)

      Prof. Dr. Hisashi Yamamoto and Prof. Dr. Hitosi Nozaki

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197801691

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      Stereo- and regioselective isomerizations, hydrolyses, and condensations can be conveniently performed with organoaluminum reagents. Examples are DATMP, (iBu)2Al[BOND]O[BOND]Al(iBu)2 (TIBAO), and Zn/Et2AlCl.

    4. Production and Utilization of Amino Acids (pages 176–183)

      Prof. Dr. Yoshiharu Izumi, Dr. Ichiro Chibata and Tamio Itoh

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197801761

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      Fortification of plant-based foods and feeds involves admixture of the deficient essential amino acid(s). These amino acids are produced on an industrial scale, e.g., by microbiological processes and by chemical synthesis.

    5. The Versatility of Tertiary Phosphane Ligands in Coordination and Organometallic Chemistry (pages 183–194)

      Prof. Dr. Ronald Mason and Prof. Dr. Devon W. Meek

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197801831

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      Research into transition metal phosphane complexes is currently concerned with four principal themes, i.e. the nature of the M[BOND]P bond, steric effects, special properties of multiphosphanes, and reactions of coordinated phosphanes.

  2. Communications

    1. Top of page
    2. Reviews
    3. Communications
    4. Abstracts
    5. Book Reviews
    1. A Stable Thiiranimine (pages 195–196)

      Prof. Dr. Gerrit L'abbé, Jean-Paul Dekerk, Dr. Jean-Paul Declercq, Dr. Gabriel Germain and Prof. Dr. Maurice Van Meerssche

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197801951

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      The first thiiranimine has now been prepared by the route shown below. The bond lengths (in pm) are shown in the formula of the compound. The unusually long S[BOND]C2 bond is opened on reaction of the three-membered ring.

    2. Intramolecular Cycloaddition of a “P[DOUBLE BOND]O-Activated” Acetyleneallene Derivative (page 196)

      Dr. Werner Winter, Dr. Albert Scheller, Thomas Butters and Walter Holweger

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197801961

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      Formation of the cyclobutaoxaphosphorin(1) is the first example of a spontaneously occurring cycloaddition of a non-perhalogenated acetylene-allene component. Compounds of type (1) were previously unknown.

    3. Divinyl Ketone as Michael Acceptor (page 197)

      Dr. Dietrich Spitzner

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197801971

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      A new mode of reaction of divinyl ketone(2) has been discovered in its reaction with anions such as (1). Under aprotic conditions, (2) undergoes single instead of double Michael addition.

    4. Complexes of Short-Chain Oligo(ethylene Glycol Ethers) Bearing only one Rigid Donor End Group (pages 197–198)

      Dipl.-Chem. Ulrich Heimann and Prof. Dr. Fritz Vögtle

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197801972

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      Crystalline complexes of alkali metal ions are formed not only by crown ethers and “noncyclic crown ethers” bearing two donor end groups but also by neutral ligand such as (1) and (2) having only one donor end group. The oligo(ethylene glycol ether) chain may be very short (n ≥ 1, i.e. with only four donor atoms per ligand).

    5. Alkaline Earth Metal Complexes of Simple Oligo(ethylene Glycol Ethers) (pages 198–199)

      Dipl.-Chem. Heinz Sieger and Prof. Dr. Fritz Vötle

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197801981

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      Structure-complexation relations of simple neutral ligands have been studied for ligands such as (1) and (2). These ligands containing donorless but rigid aryl groups form crystalline complexes, especially with alkaline earth metal ions if n ≥ 1.

    6. Novel Diylides Containing Tricoordinate Phosphorus (pages 199–200)

      Prof. Dr. Edgar Niecke and Dirk A. Wildbredt

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197801991

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      Stable compounds of tricoordinate λ5-phosphorus have now been synthesized from the SiMe3-substituted aminoiminophosphane (1) and α-alkylated diazoethanes. Compounds (2) contain two distinct ylidic centers.

    7. Use of the “Zip” Reaction for the Synthesis of a 53-Membered Polyaminolactam (pages 200–202)

      Dipl.-Chem. Urs Kramer, Armin Guggisberg, Prof. Dr. Manfred Hesse and Prof. Dr. Hans Schmid

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802001

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      The general nature of the “zip” reaction has been demonstrated by the synthesis of the decaazalactam (1) with 53 ring members. The immediate precursor, a 13-membered lactam bearing a [BOND][(CH2)3NH]9[BOND](CH2)3NH2 group at the nitrogen was obtained by the fragment-condensation method. Studies on model compounds show the ring expansion from 13 to 53 members to proceed stepwise as a “zip” reaction.

    8. Anodic NN Linkage by Oxidation of Anions of Primary and Secondary Amines (pages 202–203)

      Dipl.-Ing. Reinhold Bauer and Prof. Dr. Hartmut Wendt

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802021

      Electrochemical synthesis of hydrazines and azoalkanes can be accomplished by anodic oxidation of the amide anions of types (1) and (2). Direct anodic oxidation of NH3 or amines usually gives only very poor yields.

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    9. Triazene Transfer with Activated 2-Tetrazenes (pages 203–204)

      Dipl.-Ing. Ernst Stöldt and Prof. Dr. Richard Kreher

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802031

      N-Diazonium ions like(2) generally react in the same way as C-diazonium ions by elimination of N2. The reaction of 2-tetrazenium salts (1) with anionic nucleophiles Z shown below is new: the N3 sequence of (2) is retained in the products (3), formally the result of coupling between (2) and Z⊖.

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    10. Facile Synthesis of Functionally Substituted Cyclopentenones and Butenolides from Functional Vinyl Carbanions (pages 204–205)

      Prof. Dr. Richard R. Schmidt and Dipl.-Chem. Jörg Talbiersky

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802041

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      A substituted C3 synthon, the vinyl carbanion (2), is surprisingly formed by deprotonation of the ester (1) by strong bases. Cycloaddition to (2) gives the five-membered rings (3) and (4), which are of significance in the synthesis of natural products.

    11. Intramolecular Electron Transfer from Iron(II) to Cobalt(III) through 2,4,6-Pyridinetricarboxylate as Mediating Bridging Ligand (pages 205–206)

      Dipl.-Chem. Horst Bertram and Prof. Dr. Karl Wieghardt

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802051

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      Electron transfer between two metal ions has been studied in the complex cation (1). It decomposes in a first-order process to form one CoII and one FeIII per cation (1). Kinetic data show this electron transfer to proceed via the organic ligand which is concomitantly reduced.

    12. Regiospecific and Enantioselective Aldol Reactions (pages 206–208)

      Dipl.-Chem. Herbert Eichenauer, Dipl.-Chem. Edgar Friedrich, Dr. Werner Lutz and Dr. Dieter Enders

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802061

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      The synthetic utility of intermolecular aldol reactions was formerly limited by side reactions. Enantioselective reaction of ketones R1COCH3 with ketones R2R3CO to give the products (2) via the (known) chiral hydrazones (1) has now been accomplished.

    13. The Berson-Willcott Rearrangement of 11,11-Dimethyltricyclo[4.4.1.01,6]undeca-2,4,7,9-tetraene and Its Radical Anion (pages 208–209)

      Prof. Dr. Fabian Gerson, Dipl.-Chem. Walter Huber and Priv.-Doz. Dr. Klaus Müllen

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802081

      Thumbnail image of graphical abstract

      The nature of the frontier orbitals of a molecule is of crucial importance for the description of its valence isomerizations. The effect of transforming the neutral molecule into the radical anion has been examined for (1) [RIGHTWARDS ARROW] (3) and the corresponding process (1)[RIGHTWARDS ARROW] (3).

    14. Regioselective Synthesis of Isomeric Bicyclic Peroxides (pages 209–210)

      Prof. Dr. Waldemar Adam, Prof. Dr. A. John Bloodworth, Dr. Henny J. Eggelte and Dr. Mark E. Loveitt

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802091

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      Two complementary syntheses provide an entry to isomeric bicyclic peroxides having saturated medium-sized rings. The new approach is demonstrated for (1) and (2).

    15. Trapping of Unstable Fulvene/Singlet Oxygen Adducts by Reduction with Diazene (page 210)

      Prof. Dr. Waldemar Adam and Dr. Ihsan Erden

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802101

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      Reduction of unstable peroxides, e.g. (1) and (2), by diazene generated in situ provides a method of characterizing such compounds. The reduced adducts (3) and (4) are stable at room temperature. Remarkably, both the ketone (5) and the lactone (4) decompose with emission of light.

    16. Trapping of Unstable α-Pyrone/Singlet Oxygen Adduct by Reduction with Diazene (page 211)

      Prof. Dr. Waldemar Adam and Dr. Ihsan Erden

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802111

      Thumbnail image of graphical abstract

      Reduction of unstable peroxides, e.g. (1) and (2), by diazene generated in situ provides a method of characterizing such compounds. The reduced adducts (3) and (4) are stable at room temperature. Remarkably, both the ketone (5) and the lactone (4) decompose with emission of light.

    17. Isomerization with Methyl Migration in Trimethyl Phosphite-Arsenido and -Antimonido Complexes of Transition Metals (pages 211–212)

      Priv.-Doz. Dr. Wolfgang Malisch and Dipl.-Chem. Reinhard Janta

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802112

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      Spontaneous rearrangement of complexes(1), M = Mo or W, E = As, or M = W, E = Sb, slowly affords complexes (2) even at room temperature. The unusual basic activity of the E atom provides the driving force for this reaction.

    18. Tetraphenylphosphonium Tetrakis(difluorooxosulfimidato)borate (pages 212–213)

      Dipl.-Chem. Rainer Eisenbarth and Prof. Dr. Wolfgang Sundermeyer

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802121

      Only NSOF2 ligands are present in the anion of compound (3). Tetracoordination of the boron was deduced from the 11B-NMR spectrum.

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    19. Enantioselective Synthesis and Thermal Reorganization of an Optically Active Methyleneaziridine (pages 213–214)

      Prof. Dr. Helmut Quast and Dr. Carlos A. Weise Vélez

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802131

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      Enantioselective metalations are comparatively rare. The three-membered ring (–)-(2) has been produced in 12% optical yield by this method. Thermal rearrangement of this methyleneaziridine to the cyclopropanimine (3) is stereospecific.

    20. Difluoroarsoranes and Homologous Compounds R′R2EF2 (E = As, Sb, Bi) by Oxidative Direct Fluorination of Organoarsanes, Organostibanes, and Organobismuthanes (pages 214–216)

      Dr. Ingo Ruppert and Dr. Volker Bastian

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802141

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      Oxidative fluorination with gaseous fluorine, which proceeds without significant formation of side products in the case of tertiary phosphanes, has now been applied to the higher homologs. Largely successful suppression of element-carbon bond cleavage is surprising in the light of the decrease in the E[BOND]C bond strength on going from P to Bi.

  3. Abstracts

    1. Top of page
    2. Reviews
    3. Communications
    4. Abstracts
    5. Book Reviews
    1. ABSTRACTS (pages 216–217)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802161

  4. Book Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Abstracts
    5. Book Reviews
    1. Book Review: Organic Chemistry of Drug Synthesis. By D. Lednicer and L. A. Mitscher (page 218)

      Bernard Unterhalt

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802181

    2. Book Review: Molecular Symmetry and Group Theory. By A. Vincent (pages 218–219)

      H. G. Zachmann

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197802183

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