Angewandte Chemie International Edition in English

Cover image for Vol. 36 Issue 12

July 4, 1997

Volume 36, Issue 12

Pages 1227–1355

Currently known as: Angewandte Chemie International Edition

    1. Cover Picture (Angew. Chem. Int. Ed. Engl. 12/1997)

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199712251

      Thumbnail image of graphical abstract

      The cover picture shows a ball-and-stick model of extremely strained, highly reactive o-benzyne (1,2-didehydrobenzene) (green) inside the protective inner phase of Cram's hemicarcerand (O atoms in red, C atoms in grey, and H atoms in white). The white, circular window in the lower right-hand corner represents the inner phase in which o-benzyne was photochemically generated from incarcerated benzocyclobutenedione in two steps via benzocyclopropenone and is stable for only a short time, even at −75°C. The other three windows highlight groups of signals in the 13C NMR spectrum of the fully 13C-labeled guest molecule. More about the NMR spectroscopic properties of this molecule is reported by R. Warmuth on page 1347 ff—one hundred years after the birth of Georg Wittig, who first postulated the existence of this “dehydrobenzene”. The graphic was generated by Jan Haller, University of California, Los Angeles, CA (USA) with the program POV-ray.

  1. Reviews

    1. Top of page
    2. Reviews
    3. Highlights
    4. Communications
    5. Book Reviews
    1. Asymmetric Catalysis with Heterobimetallic Compounds (pages 1236–1256)

      Prof. Masakatsu Shibasaki, Dr. Hiroaki Sasai and Takayoshi Arai

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199712361

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      Brønsted basic and Lewis acidic like many enzymes: The multifunctional complexes shown on the right are made from a rare-earth metal (or a Group 13 element), an alkali metal, and an optically active (substituted) 2,2′-dihydroxy-1,1′-binaphthyl (BINOL) ligand. They are exceptionally suitable for asymmetric two-center catalysis of nitroaldol reactions, Michael reactions, Michael–aldol reactions, and hydrophosphonylations of imines and/or aldehydes. Ln = rare-earth metal, M1 = alkali metal, M2 = Al or Ga, HO equation image OH = BINOL.

    2. Novel Reactions of Organomolybdenum and Organotungsten Compounds: Additive–Reductive Carbonyl Dimerization, Spontaneous Transformation of Methyl Ligands into μ-Methylene Ligands, and Selective Carbonylmethylenation (pages 1258–1275)

      Prof. Dr. Thomas Kauffmann

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199712581

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      High-valent molybdenum and tungsten atoms have long been important as components of catalysts and Schrock carbene complexes. As central atoms of CH3, alkyl, and μ-CH2 complexes, they permit new, preparatively interesting reactions according to Equations (a) and (b). M1 = MoLn, WLn; M2 = MoLn, WLn, AlLn.

  2. Highlights

    1. Top of page
    2. Reviews
    3. Highlights
    4. Communications
    5. Book Reviews
    1. Free or Not, That Is the Question: Silyl and Germyl Cations in Condensed Phases (pages 1277–1280)

      Dr. Johannes Belzner

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199712771

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      “The search for an isolable silyl cation must continue” was the title of a paper in this journal a few years ago. Recently, J. Lambert et al. reported the latest results of this continued search: the trimesitylsilyl cation is a practically free silyl cation in aromatic solvents. Kinetic and thermodynamic stabilization have now also allowed the isolation of the noncoordinated germirene cation 1 by A. Sekiguchi et al.

    2. Combinatorial Chemistry for the Synthesis of Carbohydrate Libraries (pages 1280–1282)

      Dr. Prabhat Arya and Dr. Robert N. Ben

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199712801

      The first step has been made. The research groups of Hindsgaul, Boons, and Kahne have successfully synthesized libraries of di- and trisaccharides with combinatorial methods. The synthesis of this important class of oligosaccharides is thus more feasible and will have a great impact on the understanding of cell-surface interactions.

  3. Communications

    1. Top of page
    2. Reviews
    3. Highlights
    4. Communications
    5. Book Reviews
    1. Spectroscopic Detection and Theoretical Studies of a 2:1 Bromine–Olefin π Complex (pages 1284–1287)

      Prof. Dr. Roberto Bianchini, Prof. Dr. Dieter Lenoir, Prof. Dr. Rainer Herges, Jörg Grunenberg, Dr. Cinzia Chiappe and Priv. Doz. Dr. Peter Lemmen

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199712841

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      An L-shaped arrangement of bromine atoms is found in the 2:1 π complex formed by electrophilic bromination of tetraneopentylethene (see below). The reaction stops at this stage, which for the first time allows detection and determination of the thermodynamic parameters by UV spectroscopy of a 2:1 bromine–olefin complex. Theoretical calculations predict an olefin · Br2 · Br2 rather than a Br2 · olefin · Br2 structure.

    2. Enantioselective Formation of Double and Triple Helicates of Silver(I): The Role of Stacking Interactions (pages 1287–1289)

      Dr. Christophe Provent, Dr. Sujatha Hewage, Dr. Guy Brand, Dr. Loïc J. Charbonnière, Prof. Alan F. Williams and Dr. Gérald Bernardinelli

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199712871

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      Despite having ligands with almost identical conformations, the structures of the AgI complexes of 1 and 2 differ significantly: ligand 1 forms a double-helical complex of P chirality, and 2 gives a triple-helical complex (depicted on the right). The reason for the difference appears to be the existence of strong interligand stacking in the latter case.

    3. Palladium-Catalyzed Sixfold Alkenylation of Hexabromobenzene: An Interesting Case of Self-Organization (pages 1289–1292)

      Dipl.-Chem. Peter Prinz, Dr. Annegret Lansky, Dr. Burkhard Knieriem, Prof. Dr. Armin de Meijere, Dr. Thomas Haumann, Prof. Dr. Roland Boese and Dr. Matthias Noltemeyer

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199712891

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      Bowl-shaped hexakis(3,3-dimethyl-1-butenyl)benzene (1, see space-filling model on the right) was obtained from the Pd-catalyzed coupling of hexabromobenzene with 2-(3,3-dimethyl-1-butenyl)-1,3,2-benzodioxaborole. All six alkenyl groups are directed to one side of the benzene ring. Catalytic hydrogenation of 1 provides the corresponding hexakisalkylbenzene, which crystallizes in regular stacks; here the alkyl group are alternatingly above and below the ring.

    4. First Structural Characterization of a Benzophenone Ketyl Complex (pages 1292–1294)

      Dr. Zhaomin Hou, Dr. Xueshun Jia, Dr. Mikio Hoshino and Dr. Yasuo Wakatsuki

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199712921

      Thumbnail image of graphical abstract

      Highly reactive and yet isolable! The bis(benzophenone ketyl)calcium complex 1 was isolated as blue crystals from the reaction of calcium chips with benzophenone and hexamethylphosphoric acid triamide (HMPA) in THF (see below). Its X-ray crystal structure explains why benzophenone ketyl is much more reactive than fluorenone ketyl.

    5. Multicomponent Self-Assembly: Generation and Crystal Structure of a Trimetallic[4]Pseudorotaxane (pages 1294–1296)

      Dr. Paul N. W. Baxter, Prof. Dr. Jean-Marie Lehn, Dr. Hanadi Sleiman and Dr. Kari Rissanen

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199712941

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      Like a molecular lance! A rigid-rack, pyridazine-containing ligand pierces through three macrocycles (see drawing on the right), and a trimetallic pseudorotaxane is formed by CuI-assisted self-assembly. Its structure was characterized by X-ray crystallography.

    6. Cyclic Metal Complexes of Nucleobases and Other Heterocycles: Molecular Boxes, Rectangles, and Hexagons (pages 1296–1301)

      Dr. Ilpo Mutikainen, Colin J. L. Lock, Prof. Dr. Lucio Randaccio, Dr. Ennio Zangrando, Dr. Elisabetta Chiarparin, Prof. Dr. Bernhard Lippert, Dr. Holger Rauter, Dr. Pilar Amo-Ochoa, Dipl.-Chem. Eva Freisinger and Dr. Merja Blomberg

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199712961

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      Depending on the configuration of the metal unit (cis or trans) and the sequence of coordination by six-membered heterocycles uracil, 1-methylcytosine, and 2-amino-pyridine, complexes of different topologies—open box, rectangle, or hexagon—are obtained (see below). These complexes contain six or eight metal units (with PtII, NiII, PdII, CuII, or AgI; represented by spheres) in unusual relative arrangements.

    7. Quasi-Complete Solvation of Organic Molecules in the Crystalline State (pages 1301–1303)

      Dr. Alexander Shivanyuk, Dr. Volker Böhmer, Prof. Dr. Walter Vogt and Dr. Erich F. Paulus

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713011

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      The maximum possible number of hydrogen bonds to the solvent are formed by the resorcarene 1 in crystals of 1 · 18 DMSO (DMSO = dimethyl sulfoxide). Whereas highly solvated, discrete molecules of 1 are found in 1 · 18 DMSO, hydrogen-bonded, infinite columns of 1 that are entirely wrapped by layers of pyridine molecules are present in crystals of the composition 1 · 14 pyridine.

    8. PS Ligands as Building Blocks of Chiral Dimetallatetrahedranes with a Common Vertex (pages 1303–1305)

      Prof. Dr. Otto J. Scherer, Dipl.-Chem. Clemens Vondung and Dr. Gotthelf Wolmershäuser

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713031

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      A cluster with two chiral tetrahedrane fragments, which are linked through a common tungsten vertex (2), is formed on heating the tetragonal-pyramidal trinuclear complex 1 with two μ3[BOND]P[DOUBLE BOND]S ligands (Cp4 [DOUBLE BOND] C5HiPr4). The terminally coordinated PS ligand in 1 is therefore converted into a doubly side-on bound μ-η22-PS ligand.

    9. Effective Low-Temperature Aromatization of Ethane over H-Galloaluminosilicate(MFI) Zeolites in the Presence of Higher Alkanes or Olefins (pages 1305–1308)

      Dr. Vasant R. Choudhary, Anil K. Kinage and Tushar V. Choudhary

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713051

      The high thermodynamic barrier for ethane aromatization at lower temperatures (400–500°C) over a H-GaAlMFI zeolite can be overcome. Both ethane conversion and the yield of arenes drastically increase (4–80 ×) by carring out the aromatization in the presence of olefins or higher alkanes. The enhanced reactivity results from a change in the reaction mechanism, and a hydrogen-transfer reaction takes place between ethane and higher olefins.

    10. High-Yield Synthesis of [2] Catenanes by Intramolecular Ring-Closing Metathesis (pages 1308–1310)

      Dr. Bernhard Mohr, Dr. Jean-Pierre Sauvage, Prof. Robert H. Grubbs and Marcus Weck

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713081

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      Almost quantitative formation of interlocking rings results upon cyclization of threaded or intertwined complexes. The synthesis concept is based on the combination of three-dimensional template effects and ruthenium benzylidene catalyzed ring-closing metathesis (RCM, see below)

    11. Azo-Dye Rotaxanes (pages 1310–1313)

      Dr. Sally Anderson, Dr. Tim D. W. Claridge and Dr. Harry L. Anderson

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713101

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      The hydrophobic effect was used to assemble encapsulated azo dyes such as 1 in water. The dumbbell-shaped dyes were synthesized inside α-cyclodextrin, β-cyclodextrin, or a cyclophane to yield stable rotaxanes.

    12. Friedel–Crafts β-Silylvinylations (pages 1313–1315)

      Prof. Dr. Masahiko Yamaguchi, Yoshiyuki Kido, Dr. Akio Hayashi and Prof. Dr. Masahiro Hirama

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713131

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      Novel vinylgallium intermediates occur in the β-silylvinylation of aromatic hydrocarbons with trimethylsilylacetylene in the presence of GaCl3 at −78°C (see below). The interaction of silylacetylene and GaCl3 initially generates a highly electrophilic cationic species, which is attacked by arenes at the β-carbon atom. L [DOUBLE BOND] Cl, Me.

    13. Liquid-Crystal Templates for Nanostructured Metals (pages 1315–1317)

      Dr. George S. Attard, Dr. Judith M. Corker, Dr. Christine G. Göltner, Dipl.-Chem. Susanne Henke and Dr. Richard H. Templer

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713151

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      Hexagonally structured, mesoporous platinum (see picture on the right) is obtained by reduction of platinum salts in lyotropic liquid-crystalline phases. The template can be removed from the nanostructured metal colloid without affecting its structure.

    14. Asymmetric Aziridination over Ylides: Highly Stereoselective Synthesis of Acetylenyl-N-sulfonylaziridines (pages 1317–1319)

      An-Hu Li, Yong-Gui Zhou, Prof. Li-Xin Dai, Dr. Xue-Long Hou, Prof. Li-Jun Xia and Lin Lin

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713171

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      Phase-transfer conditions can be used to synthesize (−)- or (+)-cis-acetylenyl-N-sulfonylaziridines (for example 3) by the reaction of N-sulfonylimines(1) with chiral sulfonium propargylides (2) derived from D-(+)-camphor. High cis selectivity and yields as well as moderate to good ee values are characteristic for these aziridinations.

    15. Synthesis of Taxoid Ring Systems: AC [RIGHTWARDS ARROW] ABC Approach by Way of Intramolecular Alkylation (pages 1319–1321)

      Prof. Takashi Takahashi, Hajime Iwamoto, Kensuke Nagashima, Tadashi Okabe and Dr. Takayuki Doi

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713191

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      Cyanohydrin ethers are the structural elements required for intramolecular alkylation to give the eight-membered taxoid B ring. This was demonstrated both for aromatic as well as for nonaromatic C rings (see below). EE = ethoxyethyl.

    16. Cofactor-Assisted Self-Cleavage in DNA Libraries with a 3′–5′-Phosphoramidate Bond (pages 1321–1324)

      Dipl.-Chem. Jens Burmeister, Prof. Dr. Günter von Kiedrowski and Prof. Dr. Andrew D. Ellington

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713211

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      Catalytic activity in combinatorial DNA libraries is demonstrated for a cofactor-assisted self-cleavage reaction. In vitro selection allowed the isolation of one dominating sequence from a sequence library containing 72 randomized nucleotide positions. The selected sequence undergoes self-cleavage of an internal 3′–5′ phosphoramidate bond by intramolecular catalysis in the presence of the trimer pCGG (see drawing on the right).

    17. math image[P3Semath image]: A Novel Polyanion in K3RuP5Se10; Formation of Ru[BOND]P Bonds in a Molten Polyselenophosphate Flux (pages 1324–1326)

      Konstantinos Chondroudis and Prof. Dr. Mercouri G. Kanatzidis

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713241

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      An infinite, one-dimensional chelating ligandmath image[P3Semath image] is present in K3RuP5Se10 (depicted on the right), which was obtained by the reaction of ruthenium with a molten mixture of nominal stoichiometry K3P6Se26.5 at 490°C. K3RuP5Se10 is the first structurally characterized ruthenium chalcophosphate, and features very short Ru[BOND]P bonds (2.288(2), 2.262(2) Å).

    18. R2Si[DOUBLE BOND]P[BOND]SiR2F: 1,3-Sigmatropic Migration of Fluorine in a 2-Phospha-1,3-disilaallyl Derivative Capable of Conjugation and Its Conversion to Phosphadisilacyclopropanes (pages 1326–1329)

      Prof. Dr. Matthias Driess, Stefan Rell, Dr. Hans Pritzkow and Prof. Dr. Rudolf Janoschek

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713261

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      More electronically diverse than the behavior of allyl is that of the 2-phospha-1,3-disilaallyl fragment. This was confirmed by the [1,3]-sigmatropic shift of fluorine in the title compound 1, which occurred rapidly at temperatures above 40°C. Ab initio calculations show that the transition state of the migration does not have a symmetrically bridging F atom. The phosphadisilacyclopropanide 2 (R1 [DOUBLE BOND] Li(thf)x)—obtained from 1 by addition of lithium to the Si[DOUBLE BOND]P bond, subsequent elimination of LiF, and rearrangement—readily reacts to give the PH compound 3 (R1 = H). R = 2,4,6-triisopropylphenyl.

    19. Hexaphenylethane Derivatives Exhibiting Novel Electrochromic Behavior (pages 1329–1331)

      Prof. Takanori Suzuki, Jun-ich Nishida and Prof. Takashi Tsuji

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713291

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      Reversible C[BOND]C bond breaking/making as well as drastic change in color are induced upon electron transfer in the novel redox couples of hexaarylethanes 1 and bis(triarylmethyl) dications 22+. Their hysteretic redox behaviors result from the quite different geometries of 1 and 22+. Ar = p-Me2NC6H4, p-MeOC6H4.

    20. Perfectly Staggered and Twisted Difluoromethylene Groups in Perfluoroalkyl Chains: Structure of M[C4F9SO2NSO2C4F9] (M [DOUBLE BOND] Na, K) (pages 1331–1333)

      Lixin Xue, Dr. Darryl D. DesMarteau and Dr. William T. Pennington

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713311

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      The type of counterion determines whether the perfluoroalkyl chains extending from the hydrophilic core of a layered structure in compounds of the type M[CnF2m+1SO2NSO2CnF2n+1] (n, m = 4, 6) possess an all-staggered conformation (M = Na) or a more typical helical conformation (M = K; see picture on the right). In the sodium complex the perfluoroalkyl chains are too closely packed to assume a twisted conformation.

    21. Electrogenerated Chemiluminescence and Proton-Dependent Switching of Fluorescence: Functionalized Difluoroboradiaza-s-indacenes (pages 1333–1335)

      Dipl.-Chem. Matthias Kollmannsberger, Dr. Thomas Gareis, Stefan Heinl, Prof. Jörg Daub and Dr. Josef Breu

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713331

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      Suitable for light-emitting diodes or as pH sensors, the difluoroboradiaza-s-indacenes of type 1 luminesce after electrochemical excitation (X = H) or show on/off switching of fluorescence sensitivity depending on pH (X = NMe2). R1 = Me, H, CO2Et; R2 = Et, H; R3 = Me.

    22. Protonation of a Linear Oxo-Bridged Diiron Unit without Rehybridization of the Bridging Oxygen: Structure of the (μ-Hydroxo)bis-(tetraphenylporphyrinato)iron (III) Cation (pages 1335–1337)

      Dr. Daniel R. Evans, Rajeev S. Mathur, Dr. Kristel Heerwegh, Prof. Christopher A. Reed and Prof. Zuowei Xie

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713351

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      The linear Fe[BOND]O[BOND]Fe bridge in μ-oxo tetraphenylporphyrin iron(III) dimer can be protonated without structural rehybridization at the O atom (the structure of the μ-hydroxo-bridged complex is depicted on the right). Antiferromagnetic coupling between the iron centers is greatly attenuated, and proton self-exchange is slow.

    23. Tetraphosphasemibullvalene: First Valence Isomerizations in the Phosphaalkyne Cyclotetramer System (pages 1337–1340)

      Dipl.-Chem. Andreas Mack, Dr. Bernhard Breit, Dr. Thomas Wettling, Dr. Uwe Bergsträsser, Dr. Stefan Leininger and Prof. Dr. Manfred Regitz

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713371

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      Stable only up to −25°C, the semibullvalene 1 does not possess a fluctuating structure in solution at room temperature, but rather isomerizes to give the “bis(homo)prismane” 2. The latter valence isomer is accessible by numerous, widely varying routes, and the isomerization can be reversed photochemically (2 [RIGHTWARDS ARROW] 1).

    24. Rotational Spectroscopy of Mixtures of Trimethylamine and Fluorine: Identification of the Ion Pair [(CH3)3NF]+ … F in the Gas Phase (pages 1340–1342)

      Prof. Hannelore I. Bloemink, Stephen A. Cooke, Prof. A. C. Legon and Prof. John H. Holloway

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713401

      Thumbnail image of graphical abstract

      Abstraction of a F+ ion from F2 leading to formation of the ion pair [(CH3)3]NF+ … F occurs when trimethylamine and F2 are mixed in the gas phase under conditions that preclude production of F atoms. The presence of this ion pair in (CH3)3N/F2 mixtures emerging from a fast-mixing nozzle has been unambiguously established from several of its properties determined by rotational spectroscopy.

    25. Biomimetic Extradiol Cleavage of Catechols: Insights into the Enzyme Mechanism (pages 1342–1344)

      Dr. Masami Ito and Prof. Dr. Lawrence Que Jr.

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713421

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      Quantitative extradiol cleavage of a catechol derivative is achieved by exposure of complex 1 to O2 in the presence of AgBF4 and an aromatic nitrogen base. These results provide insight into how the regiochemistry of oxidative cleavage may be controlled by the metal centers of the catechol dioxygenases.

    26. The Most Iodine-Rich Polyiodide Yet: Fe3I29 (pages 1345–1346)

      Prof. Dr. Karl-Friedrich Tebbe and Dipl.-Chem. Rita Buchem

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713451

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      FcI9.67 contains bands and chains as substructures, which are linked together by up to sixfold-coordinated iodine atoms to form a novel three-dimensional network (see below). The ferrocenium ions Fc+ are intercalated in the cavities. These cations stabilize crystalline solids that contain not only known polyiodide ions but also FcI9.67, which can be described as the triply charged nonacosaiodide Fc3I29 and is the most iodine-rich polyiodide known to date.

    27. o-Benzyne: Strained Alkyne or Cumulene?—NMR Characterization in a Molecular Container (pages 1347–1350)

      Dr. Ralf Warmuth

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713471

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      One hundred years after the birth of Georg Wittig the 1H and 13C NMR spectra of o-benzyne (1) were recorded in solution. Compound 1 was generated photochemically in the inner cavity of hemicarcerand 2 from an incarcerated benzocyclobutenedione in two steps via a benzocyclopropenone hemicarceplex.

    28. The Anions [W(CH3)7] and [Re(CH3)8]2− (pages 1350–1352)

      Dipl.-Chem. Valérie Pfennig, Prof. Dr. Konrad Seppelt and Dr. Neil Robertson

      Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199713501

      Thumbnail image of graphical abstract

      Capped octahedral and square antiprismatic structures are seen for the homoleptic anions [W(CH3)7] and [Re(CH3)8]2−. Therefore these anions show no structural anomalies, in contrast to the neutral molecules [W(CH3)6] and [Re(CH3)6]. The picture on the right shows the structure of [Li(OEt2)][W(CH3)7] without the diethyl ether molecule.

  4. Book Reviews

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