Angewandte Chemie International Edition

Cover image for Vol. 45 Issue 35

September 4, 2006

Volume 45, Issue 35

Pages 5717–5893

  1. Cover Picture

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    4. Retraction
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    1. Cover Picture: Pd-Catalyzed α-Arylation of Trimethylsilyl Enol Ethers with Aryl Bromides and Chlorides: A Synergistic Effect of Two Metal Fluorides as Additives (Angew. Chem. Int. Ed. 35/2006) (page 5717)

      Weiping Su, Steven Raders, John G. Verkade, Xuebin Liao and John F. Hartwig

      Version of Record online: 1 SEP 2006 | DOI: 10.1002/anie.200690118

      A synergistic combination of two metal fluoride additives is the key to the palladium-catalyzed coupling of aryl halides with silyl enol ethers. In their Communication on page 5852 ff., J. G. Verkade, J. F. Hartwig, and co-workers discuss the use of this approach to prepare α-aryl ketones from both cyclic and acyclic silyl enol ethers and a wide range of aryl bromides and chlorides. The cover picture depicts the difference in the yields from reactions with one and with two additives.

  2. Graphical Abstract

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  3. Retraction

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      Design and Size Control of Uniform Zeolite Nanocrystals Synthesized in Adjustable Confined Voids Formed by Recyclable Monodisperse Polymer Spheres (page 5729)

      Xiaoyu Yang, Yefei Feng, Ge Tian, Yunchen Du, Xin Ge, Yan Di, Yonglai Zhang, Bo Sun and Feng-Shou Xiao

      Version of Record online: 1 SEP 2006 | DOI: 10.1002/anie.200690120

  4. Book Reviews

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  5. Highlight

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    1. Total Syntheses of the Antibacterial Natural Product Abyssomicin C (pages 5736–5739)

      René Peters and Daniel F. Fischer

      Version of Record online: 14 AUG 2006 | DOI: 10.1002/anie.200602409

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      Intra- or intermolecular: Abyssomicin C, isolated from a marine bacterium, is a potent polyketide-type antibiotic and a synthetic target of prime importance because it inhibits pathogenic bacteria. In recent independent syntheses by the Sorensen and the Nicolaou groups, intra- and intermolecular Diels–Alder reactions featured as the respective key steps for the construction of the oxabicyclo[2.2.2]octane core.

  6. Minireview

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    1. Selective Construction of Carbocyclic Eight-Membered Rings by Ring-Closing Metathesis of Acyclic Precursors (pages 5740–5750)

      Antoine Michaut and Jean Rodriguez

      Version of Record online: 31 JUL 2006 | DOI: 10.1002/anie.200600787

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      The direct approach: The direct synthesis of eight-membered carbocycles from acyclic precursors is a preparatively challenging task since entropic and enthalpic factors are unfavorable for the formation of rings of this size. Cyclooctanoids can be prepared successfully from acyclic precursors under mild reaction conditions with the help of ring-closing metathesis.

  7. Review

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    1. Polypeptides and 100 Years of Chemistry of α-Amino Acid N-Carboxyanhydrides (pages 5752–5784)

      Hans R. Kricheldorf

      Version of Record online: 1 SEP 2006 | DOI: 10.1002/anie.200600693

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      100 years young: In 2006 the chemistry of α-amino acid N-carboxyanhydrides (NCAs) marks a history of 100 years. The NCAs were used for syntheses of oligo- and polypeptides in numerous ways, and recently have played an important role in the hypothesis of molecular evolution. Peptide block copolymers, liquid-crystalline polypeptides, and the application of polypeptides as drugs or drug carriers are also discussed.

  8. Communications

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    1. Multilayer Sequential Assembly of Thin Films That Display Room-Temperature Spin Crossover with Hysteresis (pages 5786–5789)

      Saioa Cobo, Gábor Molnár, José Antonio Real and Azzedine Bousseksou

      Version of Record online: 26 JUL 2006 | DOI: 10.1002/anie.200601885

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      Assembly time: Thin films of [Fe(pyrazine){M(CN)4}] (M=Ni, Pd, or Pt) coordination polymers were assembled sequentially through coordinate bonding on gold surfaces (see scheme). These multilayers exhibit spin-crossover phenomena with hysteresis at room temperature.

    2. Total Synthesis and Structure Assignment of (+)-Hexacyclinol (pages 5790–5792)

      John A. Porco Jr., Shun Su, Xiaoguang Lei, Sujata Bardhan and Scott D. Rychnovsky

      Version of Record online: 27 JUL 2006 | DOI: 10.1002/anie.200602854

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      Structure assigned: The revised structure of (+)-hexacyclinol (1) proposed recently was confirmed following the total synthesis of the natural product. The synthesis was designed around the highly stereoselective Diels–Alder dimerization of an epoxyquinol monomer, followed by intramolecular acid-catalyzed cyclization.

    3. Thermally Responsive Vesicles and Their Structural “Locking” through Polyelectrolyte Complex Formation (pages 5792–5795)

      Yuting Li, Brad S. Lokitz and Charles L. McCormick

      Version of Record online: 31 JUL 2006 | DOI: 10.1002/anie.200602168

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      Hot spots: Thermally responsive AB diblock copolymers that self-assemble into vesicles at higher temperatures were prepared (see picture). These vesicles can be cross-linked by adding an oppositely charged polyelectrolyte.

    4. Color-Saturated Green-Emitting QD-LEDs (pages 5796–5799)

      Jonathan S. Steckel, Preston Snee, Seth Coe-Sullivan, John P. Zimmer, Jonathan E. Halpert, Polina Anikeeva, Lee-Ann Kim, Vladimir Bulovic and Moungi G. Bawendi

      Version of Record online: 28 JUL 2006 | DOI: 10.1002/anie.200600317

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      Green to the core: CdxZn1−xSe alloy core nanocrystals are synthesized and overcoated with CdyZn1−yS to create core–shell nanocrystals with the ideal wavelength of emission for quantum dot light-emitting device (QD-LED) displays. These (CdxZn1−xSe)CdyZn1−yS core–shell nanocrystals are used to fabricate color-saturated green-emitting QD-LEDs (see picture), which are suitable for display applications.

    5. Sandwich Complexes Containing Bent Palladium Chains (pages 5799–5803)

      Yasuki Tatsumi, Katsunori Shirato, Tetsuro Murahashi, Sensuke Ogoshi and Hideo Kurosawa

      Version of Record online: 25 JUL 2006 | DOI: 10.1002/anie.200601641

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      Hold the mayo! Sandwich complexes containing the arch-shaped Pd4 chain (upper structure; C blue, Pd orange) or the V-shaped Pd5 chain (lower) were synthesized and structurally characterized. The bending angles of the Pd chains reflect the p π-conjugated geometry of the template ligands.

    6. Three Groups Good, Four Groups Bad? Atropisomerism in ortho-Substituted Diaryl Ethers (pages 5803–5807)

      Mark S. Betson, Jonathan Clayden, Christopher P. Worrall and Simon Peace

      Version of Record online: 28 JUL 2006 | DOI: 10.1002/anie.200601866

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      Bring on the substitute: Even outside of macrocyclic structures, such as vancomycin, appropriate substitution can give rise to atropisomerism in diaryl ethers. Stereochemical stability about the Ar[BOND]OAr axis at room temperature or above is possible when neither of the rings is symmetrically substituted and when at least one ring carries an ortho tert-butyl group or equivalent.

    7. A Zinc–Zinc-Bonded Compound and Its Derivatives Bridged by One or Two Hydrogen Atoms: A New Type of Zn[BOND]Zn Bonding (pages 5807–5810)

      Zhongliang Zhu, Robert J. Wright, Marilyn M. Olmstead, Eric Rivard, Marcin Brynda and Philip P. Power

      Version of Record online: 14 AUG 2006 | DOI: 10.1002/anie.200601926

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      Unique interactions: Ar′ZnZnAr′ (1; Ar′=C6H3-2,6-(C6H3-2,6-iPr2)2), the dimer Ar′Zn(μ-H)2ZnAr′ (2), and the unprecedented species Ar′Zn(μ-H)(μ-Na)ZnAr′ (3) were synthesized and fully characterized. DFT calculations show that the Zn[BOND]Zn bonding interactions in 1 differ from those of other Zn[BOND]Zn compounds, and the calculations also indicate a new type of Zn[BOND]Zn bond in 3.

    8. Regioselectivity with Hemispherical Chelators: Increasing the Catalytic Efficiency of Complexes of Diphosphanes with Large Bite Angles (pages 5810–5814)

      David Sémeril, Catherine Jeunesse, Dominique Matt and Loïc Toupet

      Version of Record online: 3 AUG 2006 | DOI: 10.1002/anie.200601978

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      Control through molecular pockets: Calixarene-derived diphosphites provide effective hemispherical crowding about catalytic centers. When used in the palladium-catalyzed alkylation of cinnamyl acetate, regioselectivities higher than 98 % in favor of the linear product are observed. In the rhodium-catalyzed hydroformylation of styrene, these diphosphites lead to phenylpropionaldehyde with selectivities as high as 76 %.

    9. Conductance and Stochastic Switching of Ligand-Supported Linear Chains of Metal Atoms (pages 5814–5818)

      I-Wen Peter Chen, Ming-Dung Fu, Wei-Hsiang Tseng, Jian-Yuan Yu, Sung-Hsun Wu, Chia-Jui Ku, Chun-hsien Chen and Shie-Ming Peng

      Version of Record online: 27 JUL 2006 | DOI: 10.1002/anie.200600800

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      An alternative string theory: The current-versus-potential behavior of metal atom strings (Ni, Co, Cr) is dependent on the strength of the d-orbital coupling along the metal atom chain. Penta- and heptachromium strings each exhibit two sets of primary IV curves, which depend on whether the Cr[BOND]Cr bonds alternate and are localized, or are delocalized (see picture).

      Corrected by:

      Corrigendum: Conductance and Stochastic Switching of Ligand-Supported Linear Chains of Metal Atoms

      Vol. 45, Issue 38, 6244, Version of Record online: 19 SEP 2006

    10. Cyclodextrin Bucket Wheels: An Oligosaccharide Assembly Accommodates Metal(IV) Centers (pages 5818–5822)

      Klaus Benner, Johannes Ihringer, Peter Klüfers and Danira Marinov

      Version of Record online: 26 JUL 2006 | DOI: 10.1002/anie.200601162

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      Mining new assemblies: A molecular bucket wheel consisting of three β-cyclodextrin units, three tetrahedral tetraaqualithium cations, and a tetravalent metal center has been prepared (see picture). The assembly, held together by a series of hydrogen bonds, is also stable in solution.

    11. A Ruthenium Complex with Superhigh Light-Harvesting Capacity for Dye-Sensitized Solar Cells (pages 5822–5825)

      Chia-Yuan Chen, Shi-Jhang Wu, Chun-Guey Wu, Jian-Ging Chen and Kuo-Chuan Ho

      Version of Record online: 25 JUL 2006 | DOI: 10.1002/anie.200601463

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      Dyeing for sunlight: A new dye CYC-B1 (see picture), with the highest absorption coefficient known so far for Ru-based photosensitizers, was prepared. Solar cells sensitized with CYC-B1 have a very high current density, and the conversion efficiency of CYC-B1 is 10 % higher than that of cis-di(thiocyanato)bis(2,2′-bipyridyl-4,4′-dicarboxylate)ruthenium(II) under AM 1.5 simulated sunlight.

    12. Fluorescent Organometallic Sensors for the Detection of Chemical-Warfare-Agent Mimics (pages 5825–5829)

      Daniel Knapton, Mark Burnworth, Stuart J. Rowan and Christoph Weder

      Version of Record online: 28 JUL 2006 | DOI: 10.1002/anie.200601634

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      Mixing and matching: The highly selective detection of chemical-warfare-agent mimics can be achieved by judicious combination of carefully designed fluorescent ligands and metal ions. Designed sensor arrays of these multimetal/multiligand systems represent a modular and versatile approach for the detection of organophosphates and other analytes.

    13. Thermodynamic and Kinetic Enhancement of Electrochemical Sensitivity by Chemical Coupling in Microfluidic Systems (pages 5829–5832)

      Imtiaz M. Khalid, Qiaosheng Pu and Julio C. Alvarez

      Version of Record online: 31 JUL 2006 | DOI: 10.1002/anie.200601640

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      One helps the other: An upstream electrode (1) in a microfluidic channel drives a reaction that produces protons so that the reaction at the downstream electrode (2) becomes thermodynamically or kinetically viable. The shift in redox potential allows the analyte to be detected in conditions in which it would otherwise be undetectable.

    14. Studies on Iejimalide B: Preparation of the Seco Acid and Identification of the Molecule's “Achilles Heel” (pages 5832–5837)

      Alois Fürstner, Christophe Aïssa, Carine Chevrier, Filip Teplý, Cristina Nevado and Martin Tremblay

      Version of Record online: 4 AUG 2006 | DOI: 10.1002/anie.200601859

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      Limitations of models in total synthesis are illustrated by a study towards the potent cytotoxic macrolide iejimalide B. Although the Yamaguchi protocol allowed for the esterification of elaborate segments, attempted macrolactonization of the seco acid met with failure (see scheme, Boc= tert-butyloxycarbonyl). The assembly of the seco acid involves some of the most advanced applications of the Julia olefination known to date.

    15. Total Synthesis of Iejimalide B (pages 5837–5842)

      Alois Fürstner, Cristina Nevado, Martin Tremblay, Carine Chevrier, Filip Teplý, Christophe Aïssa and Mario Waser

      Version of Record online: 28 JUL 2006 | DOI: 10.1002/anie.200601860

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      Metathesis to the rescue: Although counterintuitive at first sight, application of ring-closing metathesis (RCM) to a cyclization precursor containing 10 double bonds has led to the selective and high-yielding formation of the macrocyclic core of iejimalide B, a potent cytotoxic agent of marine origin. In contrast, a macrolactonization approach failed to afford this intricate target.

    16. Osmium-Mediated Hexamerization of Phenylacetylene (pages 5842–5846)

      Ting Bin Wen, Zhong Yuan Zhou and Guochen Jia

      Version of Record online: 31 JUL 2006 | DOI: 10.1002/anie.200601542

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      A larger oligomer: Although transition-metal-mediated reactions of alkynes to give dimers, trimers, tetramers, and polymers are well-known, reactions of alkynes to give well-defined oligomers of medium molecular weight (e.g. pentamers, hexamers) are very scarce. The selective hexamerization of HC[TRIPLE BOND]CPh in the reaction with [OsCl(PCP)(PPh3)] (PCP=2,6-(Ph2PCH2)2C6H3; see scheme) is a rare example thereof.

    17. Radical-Mediated Alkenylation, Alkynylation, Methanimination, and Cyanation of B-Alkylcatecholboranes (pages 5847–5849)

      Arnaud-Pierre Schaffner, Vincent Darmency and Philippe Renaud

      Version of Record online: 4 AUG 2006 | DOI: 10.1002/anie.200601206

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      Radical connection: Organoboranes, prepared in situ from hydroboration of olefins with catecholborane, undergo efficient coupling reactions with vinyl and alkynyl sulfones through a radical mechanism. This procedure was also extended to the acylation and cyanation of organoboranes.

    18. Enantioselective Oxidation of Olefins Catalyzed by a Chiral Bishydroxamic Acid Complex of Molybdenum (pages 5849–5852)

      Allan U. Barlan, Arindrajit Basak and Hisashi Yamamoto

      Version of Record online: 28 JUL 2006 | DOI: 10.1002/anie.200601742

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      Excellent yields and enantioselectivities can be achieved in the molybdenum–bishydroxamic acid catalyzed asymmetric oxidation of olefins in air at room temperature with an achiral oxidant (see scheme; acac=acetylacetonate). A range of terminal, cis-, and trisubstituted olefins can be used as the substrate. Furthermore, when there are multiple double bonds, the most electron-rich is oxidized.

    19. Pd-Catalyzed α-Arylation of Trimethylsilyl Enol Ethers with Aryl Bromides and Chlorides: A Synergistic Effect of Two Metal Fluorides as Additives (pages 5852–5855)

      Weiping Su, Steven Raders, John G. Verkade, Xuebin Liao and John F. Hartwig

      Version of Record online: 17 JUL 2006 | DOI: 10.1002/anie.200601887

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      The long-sought-after palladium-catalyzed coupling of silyl enol ethers, both cyclic and acyclic, with a wide range of aryl bromides and chlorides to form α-aryl ketones is realized. The key to effective activation of the silicon enolate was the use of two metal fluoride additives, which operate in a synergistic fashion.

    20. Guest-Induced Conformational Switching in a Single Crystal (pages 5856–5859)

      Liliana Dobrzańska, Gareth O. Lloyd, Catharine Esterhuysen and Leonard J. Barbour

      Version of Record online: 27 JUL 2006 | DOI: 10.1002/anie.200602057

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      Without destruction of monocrystallinity: The conformational switching of a dinuclear metal complex between four distinct states (see picture) occurs without destroying the single crystal. This observation implies a substantial degree of cooperativity between host molecules during guest uptake, release, or exchange.

    21. Enantioselective Total Synthesis of (−)-Acylfulvene and (−)-Irofulven (pages 5859–5863)

      Mohammad Movassaghi, Grazia Piizzi, Dustin S. Siegel and Giovanni Piersanti

      Version of Record online: 1 SEP 2006 | DOI: 10.1002/anie.200602011

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      Antitumor agents (−)-acylfulvene and (−)-irofulven are prepared in an approach that employs the powerful enyne ring-closing metathesis reaction to secure the spiro-bicyclic AB rings. Other key features of this synthesis include an efficient aldol-based introduction of the stereocenter at C2, a diazene-mediated reductive allylic transposition, and a ring-closing metathesis/oxidation sequence.

    22. Enantioselective Cascade Radical Addition–Cyclization–Trapping Reactions (pages 5863–5866)

      Hideto Miyabe, Ryuta Asada, Akira Toyoda and Yoshiji Takemoto

      Version of Record online: 28 JUL 2006 | DOI: 10.1002/anie.200602042

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      In addition: The chiral Lewis acid mediated radical addition–cyclization–trapping reaction of a hydroxamate ester with two radical acceptors provides a cascade approach for the asymmetric synthesis of various γ-lactams (see scheme; Bn=benzyl, Box=bis(oxazoline), Tf=trifluoromethanesulfonyl).

    23. Design and Synthesis of Multifunctional Materials Based on an Ionic-Liquid Backbone (pages 5867–5870)

      Yuanjian Zhang, Yanfei Shen, Junhua Yuan, Dongxue Han, Zhijuan Wang, Qixian Zhang and Li Niu

      Version of Record online: 28 JUL 2006 | DOI: 10.1002/anie.200600120

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      No longer simply “green” solvents, ionic liquids can be used as backbones to integrate independent components into a multifunctional compound. For example, single-walled carbon nanotubes (SWNTs) are coupled with various anions (X) by a simple anion-exchange reaction (see picture).

    24. Total Synthesis of Pseudotrienic Acid B: A Bioactive Metabolite from Pseudomonas sp. MF 381-IODS (pages 5870–5874)

      Dominique Amans, Véronique Bellosta and Janine Cossy

      Version of Record online: 31 JUL 2006 | DOI: 10.1002/anie.200601114

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      Acid advancement: An efficient and highly convergent stereoselective synthesis of pseudotrienic acid B (see structure) has been achieved. Synthetic highlights include a crotyltitanation reaction to control the stereogenic centers at C11 and C20, a cross-metathesis reaction to synthesize the triene moiety, and a Stille cross-coupling reaction to complete the assembly of the carbon framework of the natural product.

    25. Turning Inhibitors into Activators: A Hammerhead Ribozyme Controlled by a Guanine Quadruplex (pages 5875–5878)

      Markus Wieland and Jörg S. Hartig

      Version of Record online: 27 JUL 2006 | DOI: 10.1002/anie.200600909

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      Modular design of functional RNAs can be used to tailor molecular properties. Guanosine-rich sequences were introduced as switching devices for functional nucleic acids. TMPyP4 (see picture) was identified as the strongest ribozyme inhibitor known to date. When quadruplex-forming, G-rich sequences were attached to the ribozyme, the TMPyP4-mediated response was inverted from inhibition to activation of the ribozyme reaction.

    26. Gold(III)- and Platinum(II)-Catalyzed Domino Reaction Consisting of Heterocyclization and 1,2-Migration: Efficient Synthesis of Highly Substituted 3(2H)-Furanones (pages 5878–5880)

      Stefan F. Kirsch, Jörg T. Binder, Clémence Liébert and Helge Menz

      Version of Record online: 26 JUL 2006 | DOI: 10.1002/anie.200601836

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      PtCl2-catalyzed alkyne activation initiates a domino reaction, in which a heterocyclization is followed by a 1,2-alkyl migration, for the construction of a variety of substituted 3(2H)-furanones. This stereospecific reaction is proposed to proceed through an oxonium ion intermediate (see scheme).

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      Design and Synthesis of 12-Aza-Epothilones (Azathilones)—“Non-Natural” Natural Products with Potent Anticancer Activity (pages 5880–5885)

      Fabian Feyen, Jürg Gertsch, Markus Wartmann and Karl-Heinz Altmann

      Version of Record online: 27 JUL 2006 | DOI: 10.1002/anie.200601359

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      Improving on nature: Azathilones 1 a and 1 b are “non-natural” natural products derived from epothilones through C[RIGHTWARDS ARROW]N exchange at position 12. They are highly potent inducers of tubulin polymerization (part of a microtubule is shown in the picture) and inhibit human cancer cell growth in vitro. These compounds present a new structural scaffold for microtubule stabilization and are promising lead structures for anticancer-drug discovery.

    28. Synthesis and Redox Properties of Mixed-Valent Octanuclear Iron Defective Hexacubanes and a (CaCl)-Capped Body-Centered Six-Sided Iron(III) Polyhedron (pages 5885–5889)

      Raju Prakash, Rolf W. Saalfrank, Harald Maid, Andreas Scheurer, Frank W. Heinemann, Alfred X. Trautwein and Lars H. Böttger

      Version of Record online: 28 JUL 2006 | DOI: 10.1002/anie.200601478

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      Available in assorted shapes: Three new oligonuclear complexes self-assemble from tBu-N-diethanolamine and mixtures of iron(II) and iron(III) ions. Depending on the reaction conditions, a compact or linear defective hexacubane, or a body-centered six-sided iron(III) polyhedron (see structure; Fe gold, Ca purple, C gray, N blue, O red, Cl green) is formed.

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    2. Cover Picture
    3. Graphical Abstract
    4. Retraction
    5. Book Reviews
    6. Highlight
    7. Minireview
    8. Review
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