Angewandte Chemie International Edition in English

Cover image for Vol. 16 Issue 6

June 1977

Volume 16, Issue 6

Pages 339–422

Currently known as: Angewandte Chemie International Edition

    1. Cover Picture (Angew. Chem. Int. Ed. Engl. 6/1977)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197703391

    2. Graphical Abstract (Angew. Chem. Int. Ed. Engl. 6/1977)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197703392

  1. Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Abstracts
    5. Book Reviews
    1. Recent Applications of α-Metalated Isocyanides in Organic Synthesis (pages 339–348)

      Prof. Dr. Ulrich Schöllkopf

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197703393

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      α-Metalated isocyanides owe their importance to their ambivalent character and to their being synthetic equivalents of α-metalated priamary amines.

    2. Phosphacumulene Ylides and Phosphaallene Ylides [New synthetic methods (19)] (pages 349–364)

      Prof. Dr. Hans Jürgen Bestmann

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197703491

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      Phosphacumulene ylides are phosphorus ylides and at the same time cumulenes; characteristically they form a variety of adducts at the polar ylide bond and at the C[DOUBLE BOND]C double bond. Phosphaallene ylides contain the allene double bond system.

    3. Flash Thermolysis of Organic Compounds (pages 365–373)

      Dr. Günther Seybold

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197703651

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      Thermolabile products can be prepared, even on a preparative scale, by flash thermolysis. This is impossible with conventional pyrolysis techniques.

    4. Electrophotography (pages 374–392)

      Dr. John W. Weigl

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197703741

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      The ever-increasing demand for inexpensive photocopies stimulated development of a new technology based on electrostatic imaging. How does xerography work, and what other electrophotographic processes exist? These are questions having many chemical implications.

  2. Communications

    1. Top of page
    2. Reviews
    3. Communications
    4. Abstracts
    5. Book Reviews
    1. Stereoisomeric Quinhydrones of the [2.2](1,4)Naphthalenophane Series (pages 392–393)

      Prof. Dr. Heinz A. Staab and Dipl.-Chem. Claus P. Herz

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197703921

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      The isomeric intramolecular quinhydrones (1) and (2), which have now been prepared, have surprisingly similar electronic spectra. Indirect transmission of donor-acceptor interactions might predominate in these systems.

    2. An Intramolecular Quinhydrone of the [2](1,4)Naphthaleno[2]paracyclophane Series (page 394)

      Dipl.-Chem. Claus P. Herz and Prof. Dr. Heinz A. Staab

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197703941

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      Studies on the transmission of donor-acceptor interactions are facilitated by the quinhydrone (1) and some of its derivatives which have now been synthesized as model compounds. These compounds have less pronounced CT bands than quinhydrones of the naphthalenophane series.

    3. C[BOND]C Linkage of Carboxylic Acids with Allyl Alcohols Using 2-Phenylglycine as Vehicle (pages 394–396)

      Dipl.-Chem. Norbert Engel, Dr. Börries Kübel and Prof. Dr. Wolfgang Steglich

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197703942

      A new method for the chain elongation of carboxylic acids leads to ketones under very mild conditions. Organometallic intermediates are avoided. The 2-phenylglycine used as “vehicle” does not appear in the final product.

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    4. “Noncyclic Crown Ethers”: The Terminal Group Concept (pages 396–398)

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

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197703961

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      Heteroatoms located in suitably fixed terminal groups of polyether chains can act as donors in neutral ligands. For instance, (1) forms crystalline complexes with KSCN and RbI which have a helical structure in solution.

    5. Isolation of Isomeric Iodohydroborates of Type [B10H10-nIn]2− (pages 398–399)

      Dr. Klaus-Georg Bührens and Prof. Dr. Wilhelm Preetz

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197703981

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      On iodination of the hydrodecaborate ion the equatorial and the axial positions are attacked roughly in a statistical ratio. Further substitution proceeds so as to avoid occupation of adjacent sites.

    6. 3,4-Bis(trimethylsilyl)benzocyclobutene—Synthesis by Acetylene Cotrimerization and Conversion into 1,2-Dihydrocyclobuta[c]benzyne (pages 399–400)

      Russel L. Hillard III and Professor Dr. K. Peter C. Vollhardt

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197703991

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      A facile entry to strained ring systems is provided by synthesis of the silicon compound (1), which after conversion into the 4-bromo 3-iodo derivative is transformed into 1,2-dihydrocyclobuta[c]benzyne (2). Compound (2) can be trapped as the adduct (3) with furan.

    7. Interaction between the Nonbonding Orbitals of α-Dicarbonyl Systems and π or Walsh Orbitals (pages 400–401)

      Prof. Dr. Rolf Gleiter, Dipl.-Ing. Richard Bartetzko, Dr. Peter Hofmann and Prof. Dr. Hans-Dieter Scharf

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704001

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      Double bonds and/or three-membered rings separated from 1,2-dicarbonyl systems by two σ-bonds have a surprisingly strong effect on the interaction between the nonbonding orbitals of the C2O2 moiety of molecules such as (1)(5).

    8. Triphenylsilylcarbyne Complexes of Tungsten (pages 401–402)

      Prof. Dr. Ernst Otto Fischer, Dipl.-Chem. Helmut Hollfelder, Dipl.-Chem. Peter Friedrich, Dr. Fritz Roland Kreissl and Doz. Dr. Gottfried Huttner

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704011

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      Carbyne complexes (1) and (2) contain an electron-withdrawing hetero atom. X-Ray structure analysis of (2) shows that the triphenylsilyl substituent does not affect the W---Ccarbyne bond length.

    9. Synthesis of a Stabilized 1λ5,3λ5-Diphosphacyclobutadiene (pages 402–403)

      Prof. Dr. Rolf Appel, Dr. Fritz Knoll and Dipl.-Chem. Horst-Dieter Wihler

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704021

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      The first four-membered PC ring system having partly endocyclic double bonds is present in the dication (1). Its dichloride is a stable salt (m.p. 385°C) which does not decompose in boiling water and does not display ylide reactions.

    10. Preparation of Cyclohexasilane, Si6H12 (page 403)

      Prof. Dr. Edwin Hengge and Dipl.-Ing. Dieter Kovar

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704031

      The silicon analog of cyclohexane has now been prepared from the dodecaphenyl derivative. Si6H12 probably exists in the chair form.

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    11. New Synthetic Methods for 6aλ4-Thiapentalenes (pages 403–404)

      Prof. Dr. Gerrit L'abbé, Gabriël Verhelst and Guido Vermeulen

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704032

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      No-bond resonance is a remarkable property of 1,6,6aλ4-trithiapentalenes. How do the related compounds (1), X, Y[DOUBLE BOND]O, S, NPh behave? They are now readily accessible from (2) and the aroyl derivatives Ar[BOND]CX[BOND]Cl and Ar[BOND]CY[BOND]Cl.

    12. Preparation of a β-Phosphatrimethinecyanine Dye (pages 404–405)

      Dipl.-Chem. Norbert Gamon and Prof. Dr. Christian Reichardt

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704041

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      The first β-phosphatrimethinecyanine dye has now been prepared as the tetrafluoroborate from a methyleneindoline derivative. The compound forms dark blue crystals.

    13. Column Chromatography on Triacetylcellulose. Preparative Separation of Enantiomeric Diaziridines (pages 405–406)

      FK Harri Häkli and Prof. Dr. Albrecht Mannschreck

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704051

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      Enantiomeric diaziridines of type (1) are of interest because of their chiroptical properties and because their racemization must proceed by consecutive nitrogen inversion via two mutually enantiomeric transition states. The resolution of (±)-(1) has now been accomplished.

    14. cis,trans-1,5-Cyclooctadienes (pages 406–407)

      Prof. Dr. Hans-Dieter Martin, Dipl.-Ing. Mirko Hekman, Dr. Günther Rist, Dr. Hans-peter Sauter and Dr. Daniel Belluš

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704061

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      Eight-membered rings of type (2) with trans-configurated double bonds are accessible from (1) by thermal valence isomerization. (2a) and (2b) were trapped with furan. (2c) could be isolated.

    15. (RPNCH3)4, Cyclotetra(λ3-phosphazanes)—Synthesis and Crystal Structure Analysis (pages 407–408)

      Dr. Werner Zeiss, Dr. Wolfgang Schwarz and Prof. Dr. Heinz Hess

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704071

      Thumbnail image of graphical abstract

      AP---N eight-membered ring in the ideal crown form is present in permethylated cyclo(λ3-phosphazane), which is surprisingly formed from MePCl2 and (Me3Si)2NMe. The P-ethyl derivative also contains an eight-membered ring.

    16. Synthesis of Dinuclear Complexes Containing PCl2 and PF2 Bridges (pages 408–409)

      Priv.-Doz. Dr. Wolfgang Malisch and Dr. Peter Panster

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704081

      Stable dinuclear complexes having the partial structure M---PCl2---M′ (M,M′[DOUBLE BOND][DOUBLE BOND]Cr, W) have now been synthesized. They can be transformed into the corresponding fluorine derivatives by treatment with AgBF4.

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    17. Reversible Transition between a [4]Radialene and a Cyclobutadiene by Electron Transfer (pages 410–411)

      Dr. Michael Horner and Prof. Dr. Siegfried Hünig

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704101

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      Estimates of the antiaromatic character of a cyclobutadiene from reversible potentials have now been accomplished for the first time for (1). (1) is a component of one of the few π-systems that can exist in five oxidation states connected by four reversible one-electron transfers.

    18. Symmetry and Vibrational Frequencies of Dodecahedrane (pages 411–412)

      Dr. Otto Ermer

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704111

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      For the still unknown species dodecahedrane(1) force field calculations confirm the intuitive assumption of maximum possible symmetry (Ih) for the energetically optimal molecular geometry. The Ih structure should be largely rigid (lowest vibrational frequency 395 cm-1).

    19. A General Method for the Synthesis of Sandwich-Type Complexes with a Pd[BOND]Pd or Pt[BOND]Pt Bond (pages 412–413)

      Prof. Dr. Helmut Werner and Dipl.-Chem. Alfred Kühn

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704121

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      New sandwich-type dinuclear complexes containing the L[BOND]M[BOND]M[BOND]L moiety have now been prepared from mononuclear complexes. Triisopropylphosphane is a particularly suitable ligand L.

    20. Imidazolidin-2-ones by Anodic Oxidation of Conjugated Dienes in the Presence of Dimethylurea (page 413)

      Dipl.-Chem. Herbert Baltes, Ludwig Stork and Prof. Dr. Hans J. Schäfer

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704131

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      Preparative electrolysis of dienes(1) at a graphite electrode in the presence of 1,3-dimethylurea in CH3CN/NaClO4 leads in good yields to imidazolidin-2-ones.

    21. Synthesis of α,β=Unsaturated Cyclic Ketones by Sensitized Photooxidation of Silyl Enol Ethers (pages 413–415)

      Dipl.-Chem. Edgar Friedrich and Dr. Werner Lutz

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704132

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      Regiospecific introduction of a double bond into ketones has now been achieved under such mild conditions that no racemization occurs at the adjacent chiral center.

    22. Hydrogenation of Cubane (pages 415–416)

      Dipl.-Chem. Reinhard Stober and Prof. Dr. Hans Musso

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704151

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      The relief of strain in the molecule is responsible for the order in which the bonds of the cubane skeleton are broken on hydrogenation. Cubane (R[DOUBLE BOND]H) and derivatives with R[DOUBLE BOND]CO2Me, R′[DOUBLE BOND]H and R[DOUBLE BOND]H, R′[DOUBLE BOND]CO2Me have been investigated.

    23. Crystallographic Analysis of a Topochemical Polymerization (page 416)

      Dr. V. Enkelmann and Prof. Dr. G. Wegner

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704161

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      The structure of the polymerizable diacetylene(1) has been elucidated by recording its X-ray data at 120K. (1) polymerizes to macroscopic crystals of type (2) whose structure was recently solved. Thus the coordinates of each atom are known before and after the reaction.

    24. “Carbodiphosphoranes” by a New Rearrangement of Phosphorus Ylides (pages 417–418)

      Dipl.-Chem. Anette Wohlleben and Prof. Dr. Hubert Schmidbaur

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704171

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      An unexpected reaction of methylenebisphosphonium salts such as (1) is their rearrangement to “carbodiphosphoranes” (2) on deprotonation. The bisphosphorane (3) is not formed.

    25. Reaction of Monothiodicarboximides with Phosphorous Ylides: A New Synthesis of ω-Alkylidenelactams (page 418)

      Doz. Dr. Albert Gossauer, Dr. Ralf-Peter Hinze and Harald Zilch

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704181

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      Thiocarbonyl olefination is a fitting description of the reaction sketched out below. The corresponding thiolactam is always formed as a side product by carbonyl olefination.

  3. Abstracts

    1. Top of page
    2. Reviews
    3. Communications
    4. Abstracts
    5. Book Reviews
    1. ABSTRACTS (page 419)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704191

  4. Book Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Abstracts
    5. Book Reviews
    1. Book Review: Propellanes. Structure and Reactions. By D. Ginsburg (page 420)

      Günther Maier

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704201

    2. Book Review: Isoelectric Focusing. Edited by N. Catsimpoolas (page 420)

      Kurt Hannig

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.197704202

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