Angewandte Chemie International Edition in English

Cover image for Vol. 19 Issue 9

September 1980

Volume 19, Issue 9

Pages 659–748

Currently known as: Angewandte Chemie International Edition

    1. Cover Picture (Angew. Chem. Int. Ed. Engl. 9/1980)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198006591

    2. Graphical Abstract (Angew. Chem. Int. Ed. Engl. 9/1980)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198006592

  1. Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    1. Structure and Function of the Energy-Converting System of Mitochondria (pages 659–675)

      Prof. Dr. Gebhard von Jagow and Dipl.-Biochem. Wolf Dieter Engel

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198006593

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      A study of the cell's own “power plant”—the mitochondrion—and attempts to understand its mode of operation are rewarding not only in connection with the current energy debate. Considerable advances have been made recently in the structural characterization of the participating proteins; their function has already been partly elucidated on a molecular level.

    2. Photophysical and Photochemical Processes in Micellar Systems (pages 675–696)

      Prof. Dr. Nicholas J. Turro, Prof. Dr. Michael Grätzel and Priv.-Doz. Dr. André M. Braun

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198006751

      Micelles constitute a world of their own. Photoreactions performed therein differ drastically from analogous processes in homogeneous solution; such findings can provide information about the micelles themselves and sometimes about the actual reactions. The presence in the micelle-forming molecule of a functional group participating in a photochemical reaction often leads to astonishing cooperative effects.

    3. The Structure of Simple Molecular Liquids (pages 697–708)

      Prof. Dr. Manfred D. Zeidler

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198006971

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      A theoretical understanding of the liquid state is still a long way off. The structure of molecular liquids can be described by the pair-correlation function whose principal structural parameters can be determined approximately, e.g. from scattering experiments.

  2. Communications

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    1. Inductive, CC-Hyperconjugative, and Frangomeric Effects in Solvolytic Fragmentation Reactions (pages 708–709)

      Prof. Dr. Cyril A. Grob, Dipl.-Chem. Martin Bolleter and Dr. Walter Kunz

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007081

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      The solvolytic fragmentation-substitution reaction of axial azaadamantyl bromide(1) provides the first demonstration that strong CC hyperconjugation occurs when nucleophilic solvation is sterically hindered. It was also found that the stereoelectronic conditions for CC hyperconjugation apply less strictly than those for concerted fragmentation.

    2. (R2NPO)3: A Novel Heterocycle with λ3-Phosphorus by Trimerization of an Aminooxophosphane (pages 709–710)

      Prof. Dr. Edgar Niecke, Dipl.-Chem. Hans Zorn, Prof. Dr. Bernt Krebs and Dr. Gerald Henkel

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007091

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      Formation of the novel trioxatriphosphorin(1) (X-ray structure analysis) can be rationalized in terms of a pseudo-Wittig reaction and trimerization of an aminooxophosphane.

    3. Complex-Stabilization of an Aminooxophosphane (Phosphinidene Oxide) (pages 710–712)

      Prof. Dr. Edgar Niecke, Monika Engelmann, Dipl.-Chem. Hans Zorn, Prof. Dr. Bernt Krebs and Dr. Gerald Henkel

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007101

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      The first species to have a P [DOUBLE BOND] O bond, the aminooxophosphane (iPr)2N[BOND]P [DOUBLE BOND] O, could be trapped as complex (1). Bond lengths and angles are compatible with a pseudoallylic interaction

    4. An Amino-Protecting Group for Use in Peptide Synthesis Which Can Be Introduced Electrochemically (pages 712–713)

      Dr. Mohamed Hassen Khalifa, Prof. Dr. Günther Jung and Prof. Dr. Anton Rieker

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007121

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      The new amino protecting group PChd has the following advantages: the N-(PChd) esters (3) are usually formed without racemization and in high selectivity; the group can be removed quantitatively by hydrogenolysis with regeneration of (1) (R [DOUBLE BOND] C6H5).

    5. The Ambiphilicity of 1,1-Diethoxy-4,4,4-trifluoro-3-(trifluoromethyl)-1,2-butadiene (pages 713–714)

      Univ.-Doz. Dr. Rolf W. Saalfrank, Dipl.-Chem. Winfried Paul and Heide Liebenow

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007131

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      A position intermediate between allenes and carbenes is occupied by the donor/acceptor-substituted allene (2), which was synthesized from (1) by flash thermolysis. The central C atom of (2) can be attacked by both electrophiles and nucleophiles.

    6. Photoreactions of Stilbene with Caffeine: Known, and New Types of Reactions (pages 714–715)

      Prof. Dr. Gerd Kaupp and Heinz-Willi Grüter

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007141

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      New reactions for which no precedent is known are nowadays discovered only rarely. This has now been accomplished in the photochemical reaction of stilbene with caffeine. Compounds (1) to (3) are formed by novel reactions.

    7. 1,2,3,5,6,7-s-Hydrindacenehexone and 1,2,3,6,7,8-Pyrenehexone—Two New Strong Acceptors (pages 715–716)

      Prof. Dr. Rolf Gleiter and Dipl.-Ing. Peter Schang

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007151

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      The hexaketones (1) and (2), now synthesized for the first time, each have two vicinal tricarbonyl groups; as expected, they are found to be strong acceptors. Their halfwave potentials resemble the value for tetracyanoquinodimethane. (1) and (2) form 1:1 complexes with pyrene.

    8. Iminium-Activated Azides—New Reagents for the Transfer of Diazonium or Diazo Groups (pages 716–717)

      Dr. Bruno Kokel and Prof. Dr. Heinz Günter Viehe

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007161

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      The transfer of diazonium and diazo groups in acid solution can be accomplished with the reagent (1). For instance, it can transform phenol derivatives into diazonium chlorides, and 1,3-diketones into diazo compounds.

    9. Photochemical Reductive cis-Elimination in cis-Diazidobis(triphenylphosphane)platinum(II) Evidence of the Formation of Bis(triphenylphosphane)platinum(0) and Hexaazabenzene (pages 717–718)

      Prof. Dr. Arnd Vogler, Dr. Robin E. Wright and Dr. Horst Kunkely

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007171

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      Can cyclo-N6 exist? Evidence for the formation of this formal benzene analogue was obtained on irradiation of the complex (1) at 77 K. Unequivocal proof will probably be extremely difficult. The much-discussed intermediate (2) could be characterized for the first time by emission spectroscopy.

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    10. Carbonates and Polycarbonates from Urea and Alcohol (pages 718–720)

      Dr. Peter Ball, Dipl.-Chem. Heinz Füllmann and Prof. Dr. Walter Heitz

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007181

      The title reaction—so convincing on paper—succeeds only in the presence of the right catalysts. Combinations of a weak Lewis acid and a Lewis base, e.g. diisobutylaluminum hydride/triphenylphosphane, accelerate formation of carbonate from carbamic esters and alcohols to such an extent that the competing elimination of isocyanic acid is suppressed.

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    11. N-Ethynylamines of the Type R[BOND]NH[BOND]C[TRIPLE BOND]C[BOND]H (pages 720–721)

      Dipl.-Chem. Hans-Wilhelm Winter and Prof. Dr. Curt Wentrup

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007201

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      The first N-ethynylamines such as (2) with secondary amino groups were obtained by flash vacuum pyrolysis of (1) in a special apparatus fitted with facilities for IR spectroscopy. (2) is transformed into N-phenylketenimine at - 70°C.

    12. New Dihydrido-Bridged Binuclear Platinum-Iridium Complexes (pages 721–722)

      Dr. Attilio Immirzi, Dr. Alfredo Musco, Dr. Paul S. Pregosin and Prof. Luigi M. Venanzi

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007211

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      Complexes having two bridging H atoms between two different metal atoms are rare. (1), R = Ph, has been isolated as the BPh4 salt. The cation (1a) exists up to - 60°C; above - 30°C the R and Et3P groups attached to Pt exchange their positions until a 1:1 mixture of (1a) and (1b) is obtained.

    13. The[DOUBLE BOND]PCN Group as a Pseudochalcogen; Cyanophosphinidene-Substituted Heterocycles (pages 722–723)

      Prof. Dr. Alfred Schmidpeter, Wolfgang Gebler, Dipl.-Chem. Franz Zwaschka and Priv.-Doz. Dr. William S. Sheldrick

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007221

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      The pseudochalcogen character of [DOUBLE BOND]PCN postulated in the “cyano displacement principle” could be confirmed for the benzimidazoline derivative (1), R[DOUBLE BOND]CH3. (1) (X-ray structure analysis) forms air-stable crystals.

    14. The Diphenylbismuthyl Group—A Potential New Auxiliary Group in Organic Synthesis (pages 723–724)

      Dipl.-Chem. Fritz Steinseifer and Prof. Dr. Thomas Kauffmann

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007231

      The PH2Bi group possesses a combination of favorable properties that is so far unique: Ph2Bi (like other organo-heavy metal groups) stabilizes a carbanionic center; the alkyl-Bi bond in alkyldiphenylbismuthanes is cleaved selectively by chlorine and bromine below 0°C; Ph2Bi can be replaced by H or Li under mild conditions if the resulting Li compound is stabilized.

    15. 6-Oxoverdazyls (pages 724–725)

      Prof. Dr. Franz A. Neugebauer and Hans Fischer

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007241

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      New highly stable monomeric radicals(1) have been synthesized from 2,4-carbonohy-drazides and aldehydes. (1a), R1[DOUBLE BOND]H, and (1b), R1[DOUBLE BOND]C6H5, form yellow and red crystals, respectively.

    16. Asymmetric Synthesis of Amines by Carbon-Carbon Coupling in the α-Position to Nitrogen (pages 725–726)

      Dr. Michael Kolb and Jacqueline Barth

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007251

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      Optically active amines of type(3) and (4) from propargylamine (1) can be obtained by use of the chiral auxiliary compound (S)-(2); the auxiliary compound is recycled in this synthesis. (3) and (4) can be transformed, for example, into amino acids and heterocycles.

    17. Tripropylcarbazoyllithium (pages 726–728)

      Dr. Valentin Rautenstrauch and Dr. Francois Delay

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007261

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      The title compound (1) is a synthetically useful new acyllithium derivative. It reacts, e.g. with aldehydes, esters, and alkyl halides to form α-hydroxylalkyl-, α-oxoalkyl-, and alkylcarbohydrazides.

    18. A Theoretical Investigation of the Diethynylcyclobutadiene(cyclopentadienyl)cobalt Rearrangement (pages 728–729)

      Priv.-Doz. Dr. Peter Hofmann and Prof. Dr. Thomas A. Albright

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007281

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      The fascinating rearrangement (1) [RIGHTWARDS ARROW] (2) is shown by theoretical considerations not to proceed via the proposed plausible intermediates. No arguments oppose the direct conversion of (1) into an intermediate having R2-substituted 1,5-cyclooctadiene-3,7-diyne ligands.

    19. Characterization by Mössbauer Spectroscopy of Iron Carbide Phases in a Highly Active Carbon Matrix Catalyst for Medium Pressure Fischer-Tropsch Synthesis (pages 729–731)

      Dr. Hartwig Schäfer-Stahl

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007291

      An improved understanding of the Fischer-Tropsch synthesis (CO + H2 [RIGHTWARDS ARROW] hydrocarbons), and especially of the processes occurring at the catalyst, is of great topical interest. Reduction of an FeCl3-graphite intercalation compound by biphenyllithium afforded an amorphous carbon layer matrix with embedded highly dispersed Fe particles. In the presence of CO and H2 (140°C, medium pressure range) the Fe particles are transformed mainly into iron carbide phases. This highly active catalyst has now been treated at various temperatures with gas mixtures having different H2 contents. It is deduced from the catalytic activity and the Müssbauer spectra that iron carbide phases are the actual catalyst, at least below 200°C.

    20. Facile Synthesis of α- and β-O-Glycosyl Imidates; Preparation of Glycosides and Disaccharides (pages 731–732)

      Prof. Dr. Richard R. Schmidt and Dipl.-Chem. Josef Michel

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007311

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      Simplification of glycoside and saccharide syntheses is possible with the aid of the readily isolable β- and α-glycosyl imidates (1) and (2). These key compounds are conveniently prepared from C-1-unprotected glucopyranose. Compounds of type (2) were formerly unknown.

    21. N-Sulfinylnonafluorobutanesulfonamide—A Supernucleophile (pages 732–737)

      Dipl.-Chem. Reinhard Bussas and Prof. Dr. Günter Kresze

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007321

      The transformation of a highly reactive enophile into the supernucleophile (1) has been accomplished by formal replacement of p-tolyl by n-C4F9. The readily accessible compound (1) is some 103 to 104 times as active as its p-tolyl analogue.

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    22. 3-Oxa-Ene Reactions of N-Sulfinylnonafluorobutanesulfonamide with Alkanones—General Synthesis of 2-Oxoalkanesulfinic Acid Derivatives (pages 737–739)

      Prof. Dr. Günter Kresze and Dipl.-Chem. Reinhard Bussas

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007371

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      Reactions of the supernucleophile (1) with ketones, R1 = alkyl or aryl, proceed via the enol forms. Such 3-oxa-ene reactions are of interest in connection with oxidations by SeO2.

    23. Direct Detection of Dicyanoketene in the Gas Phase (pages 739–740)

      Dr. Alfred Hotzel, Prof. Dr. Richard Neidlein, Dipl.-Chem. Reinhard Schulz and Prof. Dr. Armin Schweig

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007391

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      The characterization of dicyanoketene(2), only recently proposed as reactive intermediate of the thermal decomposition of (1), has been achieved by PE spectroscopy and, independently, by mass spectrometry.

    24. Direct Detection of Dicyanothioketene in the Gas Phase (pages 740–741)

      Dipl.-Chem. Reinhard Schulz and Prof. Dr. Armin Schweig

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007401

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      Dicyanothioketene (2), the very first thioketene, has been generated at 470°C/0.05 mbar from (1) and characterized by variable temperature PE spectroscopy (VTPES).

    25. Lithium Dibenzoylphosphide · 1,2-Dimethoxyethane—A New 2-Phospha-1,3-dionate (pages 741–742)

      Prof. Dr. Gerd Becker, Matthias Birkhahn, Dr. Werner Massa and Dipl.-Chem. Werner Uhl

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007411

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      The lithium compound (1) was formed in place of dibenzoylphosphane on reaction of LiPH2 DME with PhCOCI. In its crystal, (1) exists as a dimer having a four-membered (LiOLiO) ring and pentacoordinated lithium.

    26. Direct Method for the Synthesis of N-Boc-L-3,4-didehydroproline (pages 742–743)

      Dr. Jean-Robert Dormoy, Prof. Dr. Bertrand Castro, Dr. Georges Chappuis, Ulrich Stefan Fritschi and Dr. Peter Grogg

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007421

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      Use of naturally occurring L-4-hydroxyproline as starting material for the title compound permits far simpler synthesis than older procedures which require resolution of optical isomers. The key step is pyrolysis of the esterified starting material which has been converted into the S-methyl xanthogenate.

    27. Dehydroxylation of Hydrogen Zeolites: Conditions for the Preparation of Thermally Stable Catalysts (pages 743–745)

      Dr. Laszlo Marosi

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007431

      The elimination of water from hydrogen zeolites proceeds in two steps: (i) between ca. 320 and 550°C water is eliminated from hydroxy groups coordinated to adjacent framework aluminum atoms; (ii) between ca. 550 and 630°C water elimination proceeds via migration of framework aluminum atoms into the intracrystalline pore system. Suitable choice of conditions, especially in the last stage, provides a means of influencing the quality of the resulting zeolite catalysts. Too fast a heat-up rate between 500 and 600°C causes the crystal lattice to collapse.

    28. Amorphous Zeolites (pages 745–746)

      Prof. Dr. John M. Thomas and Dr. Leslie A. Bursill

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007451

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      An insight into the structure of zeolites lacking long-range order but with pronounced ion-exchange properties is provided by high-resolution electron microscopy. Individual supercages and regions made up of ca. 30 to 100 supercagesareseenintheamorphousmatrix.

    29. Bis(η-cyclopentadienyliron-μ,η-thiadiborolene)iron—Structure of a η-C5H5 Tetradecker Sandwich Complex (pages 746–747)

      Prof. Dr. Walter Siebert, Dr. Christian Böhle and Priv.-Doz. Dr. Carl Krüger

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198007461

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      A new entry to η-C5H5 tetradecker sandwich complexes (2), M = Fe or Co, starts from [CpFe(C2B2S)]2Zn, which gives the long-sought sandwich anion (1) on treatment with potassium. (1) reacts with FeCl2 or CoCl2 to form the complexes (2). An X-ray structure analysis has been performed on (2), M = Fe.

  3. Book Reviews

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

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