Angewandte Chemie International Edition in English

Cover image for Vol. 18 Issue 1

January 1979

Volume 18, Issue 1

Pages 1–88

Currently known as: Angewandte Chemie International Edition

    1. Cover Picture (Angew. Chem. Int. Ed. Engl. 1/1979)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900011

    2. Graphical Abstract (Angew. Chem. Int. Ed. Engl. 1/1979)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900012

  1. Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    1. From the Principle of Areno-Analogy to Heterocyclopolyaromatic Compounds (pages 1–19)

      Prof Dr. Thomas Kauffmann

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900013

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      “Ring of rings” is one description of heterocyclopolyaromatic compounds; a more fitting one is “cyclic compounds containing heteroaromatic, and possibly aromatic, moieties as ring members”. These combinations offer enormous variety.

    2. The Art of Titration. From Classical End Points to Modern Differential and Dynamic Analysis (pages 20–49)

      Dr. Ruthild Winkler-Oswatitsch and Prof. Dr. Manfred Eigen

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900201

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      Titration is by no means a routine matter, as the chemist knows from experience. Instead, each problem requires an optimized procedure. An understanding of the physical principles involved is therefore essential. The art of titration is as little related to the mechanical execution of recipes as is the art of cooking.

    3. Plastics as Optical Materials (pages 49–59)

      Dr. Helmut Dislich

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900491

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      Numerous applications of “organic” plastics in optics have been reported. Thus UV light guides consist of a quartz glass core surrounded by a plastic coating; there is no glass with a sufficiently low refractive index. Lenses for sunglasses and safety spectacles can be produced more economically from plastics than from glass.

  2. Communications

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    1. Synthesis and Structure of the nido-Cluster (CH3)5C5Sn+ (pages 59–60)

      Prof. Dr. Peter Jutzi, Dipl.-Chem. Franz Kohl and Dr. Carl Krüger

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900591

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      The pentagonal-pyramidal η5-cyclopentadienyltin(II) cation(1). hitherto observed only in mass spectra, has been isolated as the tetrafluoroborate. The structure of this nido cluster has been confirmed by X-ray analysis.

    2. Bis(trimethylislyl)zinc and -cadmium (pages 60–61)

      Priv.-Doz. Dr. Lutz Rösch and Dipl.-Chem. Gerald Altnau

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900601

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      The first alkylsilylzinc compound (1) [and its cadmium analog (2)] could be synthesized from ZnX2 [and CdX2] and LiAl(SiMe3)4. Neither of the “silaorganometallic compounds” is thermally very stable. Their spectra are suggestive of a linear Si—M—Si arrangement and fast exchange of the Me3Si groups in (2).

    3. Coordination Number 3 in CoII: Na10[Co4O9], an Oligooxocobaltate(II) (pages 61–62)

      Dipl.-Chem. Wilfried Burow and Prof. Dr. Rudolf Hoppe

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900611

      The first compound of cobalt in a trigonal-planar environment, viz. Na10[Co4O9] has been obtained in the form of red single crystals by annealing of Na2O and “active” CoO in sealed cobalt tubes. The oxide is extremely sensitive to moisture, and also consitutes the first oxocobaltate(II).

    4. Extreme Liquid Chromatographic Separation Effects in the Case of Diastereomeric Amides Containing Polar Substituents (pages 62–63)

      Dr. Günter Helmchen, Dipl.-Chem. Günter Nill, Dipl.-Chem. Dieter Flockerzi, Willi Schühle and Dr. Mohamed S. K. Youssef

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900621

      Thumbnail image of graphical abstract

      Routine separations of enantiomers may soon be common laboratory practice. On the basis of chromatographic data, four postulates were derived which serve as guidelines in the search for the structural feature of the amides (1)/(2) necessary for high separation factors α. The highest value of α = 5.77 has been found for (1)/(2), R1[DOUBLE BOND](CH2)2OH, A1[DOUBLE BOND]CH2OH, R2=A2[DOUBLE BOND]Ph; this is for separation on silica gel! Separations with α≳2 are possible on simple columns.

    5. Preparative Scale Directed Resolution of Enantiomeric Carboxylic Acids and Lactones via Liquid Chromatography and Neighboring-Group Assisted Hydrolysis of Diastereomeric Amides (pages 63–65)

      Dr. Günter Helmchen, Dipl.-Chem. Günter Nill, Dipl.-Chem. Dieter Flockerzi and Dr. Mohamed S. K. Youssef

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900631

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      The separation of enantiomeric carboxylic acids (1) on a preparative scale (1 mol) can be accomplished by the following reaction sequence: transformation of (1) with optically active amines, e.g. (2), containing polar groups, into diastereomeric amides [RIGHTWARDS ARROW] separation of the amides by liquid chromatography on silica gel columns [RIGHTWARDS ARROW] mild acidic hydrolysis. Amines such as (3) without additional polar groups suffice for separation of lactones.

    6. Preparative Scale Directed Resolution of Enantiomeric Amines via Liquid Chromatography of Diastereomeric 4-Hydroxybutyramides (pages 65–66)

      Dr. Günter Helmchen and Dipl.-Chem. Günter Nill

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900651

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      The separation of enantiomeric amines (1) on a preparative scale can be carried out by the same principles as used in the separation of enantiomeric carboxylic acids. However, there is no simple access to amides bearing α-substituents in the acidic moiety; the corresponding 2-alkylbutyrolactones racemize. 3-Substituted butyrolactones such as (2) proved to be suitable reagents.

    7. Xe(OTeF5)6, A Deep-Colored Noble Gas Compound, and O[DOUBLE BOND]Xe(OTeF5)4—The Existence of Kr(OTeF5)2 (pages 66–67)

      Dipl.-Chem. Dieter Lentz and Priv.-Doz. Dr. Konrad Seppelt

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900661

      The red-violet color of Xe(OTeF5)6(1) must be attributed to the bonding state of hexavalent xenon which possesses a nonbonding electron pair: Te(OTeF5)6 has no such pair and is colorless. The extremely light-sensitive compound (1) probably exists as a monomeric molecule with covalent bonds.

      • equation image
    8. Vinyl Ketenimines by Nucleophilic Ring Cleavage of Cyclopropenes with tert-Butyl Isocyanide (pages 67–68)

      Prof. Dr. Günter Ege and Dipl.-Chem. Karlheinz Gilbert

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900671

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      Vinylketenimines were previously unknown, with one exception. A new entry to this class of compounds has now been discovered. The reaction does not involve a bicyclobutanimine.

    9. Oxidation of Hydrocarbons with Benzyl(triethyl)ammonium Permanganate (pages 68–69)

      Dipl.-Chem. H.-Jürgen Schmidt and Prof. Dr. Hans J. Schäfer

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900681

      Thumbnail image of graphical abstract

      Oxidation of CH bonds by permanganate in organic solvents becomes possible on use of the salt benzyl(triethyl)ammonium permanganate. Hydrocarbons such as (1) and (2) are oxidized mainly to ketones and tertiary alcohols, repectively, while ethers such as (3) give esters.

    10. Oxidation of Ethers with Benzyl(triethyl)ammonium Permanganate (pages 69–70)

      Dipl.-Chem. H.-Jürgen Schmidt and Prof. Dr. Hans J. Schäfer

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900691

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      Oxidation of CH bonds by permanganate in organic solvents becomes possible on use of the salt benzyl(triethyl)ammonium permanganate. Hydrocarbons such as (1) and (2) are oxidized mainly to ketones and tertiary alcohols, repectively, while ethers such as (3) give esters.

    11. Intermolecular Ene Reactions in a High-Pressure/High-Temperature Flow Apparatus (pages 70–71)

      Dr. Jürgen Metzger and Prof. Dr. Peter Köll

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900701

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      A simple “HP-HT” apparatus provides the frequently cited “suitable conditions” for many reactions which cannot (yet) be accomplished by other methods. Such processes are ene reactions between nonactivated components like (1) and (2), and pericyclic reactions between alkyanes and alkanes (“ane reactions”).

    12. Thermal Pericyclic Reaction between Alkynes and Alkanes (page 71)

      Dr. Jürgen Metzger and Prof. Dr. Peter Köll

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900711

      Thumbnail image of graphical abstract

      A simple “HP-HT” apparatus provides the frequently cited “suitable conditions” for many reactions which cannot(yet) be accomplished by other methods. Such processes are ene reactions between nonactivated components like (1) and (2), and pericyclic reactions between alkynes and alkanes (“ane reactions”).

    13. General Synthesis of Potentially Antiviral α-Adamantyl Carbonyl Compounds (page 72)

      Doz. Dr. Manfred T. Reetz, Dipl.-Chem. Wilhelm F. Maier, Konrad Schwellnus and Ioannis Chatziiosifidis

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900721

      Thumbnail image of graphical abstract

      The antiviral activity of some α-adamantyl carbonyl compounds of type (3) is greater than that of 1-amino-adamantane. Syntheses of the kind shown below are therefore of considerable interest.

    14. C-Acylation under Virtually Neutral Conditions (pages 72–74)

      Dr. Dee W. Brooks, Ms. Linda D.-L. Lu and Professor Dr. Satoru Masamune

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900722

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      Acylations is syntheses of natural products often have to be performed under very mild conditions. The neutral Mg salt of a malonic thiol half-ester of type (1) permits acylation of imidazolides (Im=1-imidazolyl) in practically neutral solution. Numerous acid- and base-labile groups survive this treatment.

    15. Cyclooligocondensation of Amino Acids: Macrocyclic Amides of β-Alanine (pages 74–75)

      Prof. Dr. Manfred Rothe and Dr. Dietger Mühlhausen

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900741

      Nitrogen analogs of crown ethers of type (2) have recently atracted much attention. The reaction β-alanine [RIGHTWARDS ARROW] (1) [RIGHTWARDS ARROW] (2) provides the simplest entry yet to these compounds. The tendency to form large rings in macrocyclization equilibria could be estimated for β-alanine [RIGHTWARDS ARROW] (1).

      • equation image
    16. Thermolysis of Arenediazonium Pentacarbonylcyano-6A-metalates in Various Media: A Route to Novel α-Functionalized Isocyanides (pages 75–76)

      Dr. Wolf Peter Fehlhammer and Dipl.-Chem. Fritz Degel

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900751

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      A new route to complexed isocyanides—including those with strongly electronegative substituents which were previously inaccessible, e.g. CNCCl3—is seen in the accompanying reaction scheme. The aryl radical ArN  N or Ar reacts with the solvent H  R via H abstraction; the resulting R combines with the radical cyano complex.

    17. Reversible Opening of a Trinuclear Heterometal Cluster (pages 76–77)

      Prof. Dr. Gottfried Huttner, Josef Schneider, Dr. Hans-Dieter Müller, Dr. Gerhard Mohr, Dipl.-Chem. Joachim von Seyerl and Lidwina Wohlfahrt

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900761

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      The mode of action of metal clusters in homogeneous catalysis is hardly known. The first proof that clusters can reversibly add substrates (L[DOUBLE BOND]CO, PPh3) via opening of metal-metal bonds has now been obtained.

    18. Catalytic Alkylation of Benzene with CO and H2: A Homogeneously Catalyzed Fischer-Tropsch Synthesis (pages 77–78)

      G. Henrici-Olivé and S. Olivé

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900771

      The synthesis of alkylbenzenes from benzene, CO, and H2 constitutes the first demonstration of true Fischer-Tropsch chain growth on a soluble mononuclear catalyst [W(CO)6(+AlCl3)]. Reaction is performed at 200°C under pressure. No xylene is formed.

    19. Ring-Opening of 5-(Bromomethyl)-2-isoxazolines to β,γ-Enoximes—A New Principle for the γ-Substitution of Allyl Bromides by α-Functionalized Alkyl Groups (pages 78–80)

      Dr. Volker Jäger, Dr. Hartmut Grund and Dipl.-Chem. Wilfried Schwab

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900781

      Thumbnail image of graphical abstract

      Reductive-eliminating ring opening of isoxazolines(2) is the key step of a reaction sequence for controlled γ-substitution of allyl bromides (1). The reaction may give oximes (3), ketones (4), or their secondary products.

    20. Six-Coordinate Hydrogen: Structure of [(Ph3P)2N]+[HCo6(CO)15] by Single-Crystal Neutron Diffraction Analysis (pages 80–81)

      Dr. Donald W. Hart, Dr. Raymond G. Teller, Miss Chiau-Yu Wei, Prof. Dr. Robert Bau, Dr. Giuliano Longoni, Dr. Stefano Campanella, Prof. Dr. Paolo Chini and Dr. Thomas F. Koetzle

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900801

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      A hydrogen atom at the center of an octahedral cage of cobalt atoms—that is a striking structural feature of the title compound which is the first of its kind to be accurately characterized by neutron diffraction in a single crystal. Only few examples of such “interstitial” hydride ligands are known for covalent complexes. The apparent radius of the H atom is 0.53Å; it can readily enter and leave its “metal cage”.

    21. [(triphos)Co(δ-P3)Cr2(CO10)]: A Trinuclear Heterometal Complex Containing cyclo-Triphosphorus as μ3-Ligand (pages 81–82)

      Dr. Stefano Midollini, Dr. Annabella Orlandini and Prof. Dr. Luigi Sacconi

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900811

      Thumbnail image of graphical abstract

      The P atoms of the P3 ring in the complex (triphos)Co(δ-P3) still possess donor properties. Hence the complex can react with Cr(CO)6 in the molar ratio 1:1 or 1:2 to give a di-or trinuclear complex (1). The original “donor complex” with a CoP6 skeleton remains almost unchanged on bonding to the Cr(Co)5 groups.

    22. Preparation of a New Series of Trinuclear Metallophthalocyanines and -porphyrins (pages 82–83)

      Prof. Dr. Shinzi Kato, Ippei Noda, Prof. Dr. Masateru Mizuta and Yuji Itoh

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900821

      Thumbnail image of graphical abstract

      In the μ-carbido complex(4), obtained as shown below, the tin atom is linked to the rhenium atoms via a carbide carbon atom which bonds like a carbyne to the rhenium (TPP stands for tetraphenylporphyrin). An impression of the spatial arrangement of the complexes of type (3), which are formed at only slightly higher temperatures than (4), is provided by the adjacent formula.

    23. A Metalloporphyrin Containing Carbyne-like Carbido Carbon: 5,10,15,20-Tetraphenylporphyrinato[bis(μ-carbidotricarbonylrhenium)]tin(IV) (page 83)

      Ippei Noda, Prof. Dr. Shinzi Kato, Prof. Dr. Masateru Mizuta, Prof. Dr. Noritake Yasuoka and Prof. Dr. Nobutami Kasai

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900831

      Thumbnail image of graphical abstract

      In the μ-carbido complex(4), obtained as shown below, the tin atom is linked to the rhenium atoms via a carbide carbon atom which bonds like a carbyne to the rhenium (TPP stands for tetraphenylporphyrin). An impression of the spatial arrangement of the complexes of type (3), which are formed at only slightly higher temperatures than (4), is provided by the adjacent formula.

    24. Carbonylation of Lithium Dialkylamides to Give Carbamoyllithiums (pages 83–85)

      Dr. Valentin Rautenstrauch and Dr. Michel Joyeux

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900832

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      “True” acyl anions would be desirable as synthetic reagents, but are inaccessible. Only some N,N-disubstituted carbamoyllithium compounds such as (1), which have presumably ionic, angular structures, are persistent in solution. Further carbonylation of (1) affords interesting secondary products, e.g. hydroxymalonamide (2), N-Monosubstituted lithium amides such as (3) rearrange to N-lithioformamides (4) on carbonylation.

    25. Carbonylation of Lithium Monoalkylamides to Give N-Lithio(alkyl)formamides (pages 85–86)

      Dr. Valentin Rautenstrauch and Dr. Michel Joyeux

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900851

      Thumbnail image of graphical abstract

      “True” acyl anions would be desirable as synthetic reagents, but are inaccessible. Only some N,N-disubstituted carbamoyllithium compounds such as (1), which have presumably ionic, angular structures, are persistent in solution. Further carbonylation of (1) affords interesting secondary products, e.g. hydroxymalonamide (2), N-Monosubstituted lithium amides such as (3) rearrange to N-lithioformamides (4) on carbonylation.

  3. Book Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    1. Book Review: Optoacoustic Spectroscopy and Detection. Edited by Yoh-Han Pao (page 86)

      Egon Fahr

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900861

    2. Book Review: Principles of Colloid and Surface Chemistry. By P. C. Heimenz (page 86)

      Klaus Christmann

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900862

    3. Book Review: Liquid Fuels from Coal. Edited by R. T. Ellington (pages 87–88)

      K. Hedden

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197900872

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