Angewandte Chemie International Edition

Cover image for Vol. 44 Issue 38

September 26, 2005

Volume 44, Issue 38

Pages 6087–6251

    1. Cover Picture: Real-Time Observation of Ionization-Induced Hydrophobic[RIGHTWARDS ARROW]Hydrophilic Switching (Angew. Chem. Int. Ed. 38/2005) (page 6087)

      Shun-ichi Ishiuchi, Makoto Sakai, Yuji Tsuchida, Akihiro Takeda, Yasutake Kawashima, Masaaki Fujii, Otto Dopfer and Klaus Müller-Dethlefs

      Article first published online: 20 SEP 2005 | DOI: 10.1002/anie.200590126

      The intermolecular binding motif of the argon atom in a phenol⋅⋅⋅Ar dimer has been monitored on the picosecond timescale by time-resolved UV–UV(pump)–IR(probe) ionization depletion spectroscopy. The cover picture shows the dynamic process, which involves a shift of the initially π-bound Ar atom to a hydrophilic, hydrogen-bound site. For more details, see the Communication by M. Fujii, K. Müller-Dethlefs, and co-workers on page 6149 ff.

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    3. Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture) (pages 6110–6127)

      Richard Axel

      Article first published online: 20 SEP 2005 | DOI: 10.1002/anie.200501726

      A sense of occasion: Around 20 years after the start of their pioneering studies on the function of the nose and brain in odor perception, R. Axel and L. Buck have received the 2004 Nobel Prize for Medicine or Physiology. The picture shows schematically the coding of different odors in the olfactory epithelium (OE) and olfactory bulb (OB).

    4. Unraveling the Sense of Smell (Nobel Lecture) (pages 6128–6140)

      Linda B. Buck

      Article first published online: 20 SEP 2005 | DOI: 10.1002/anie.200501120

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      A sense of occasion: Around 20 years after the start of their pioneering studies on the function of the nose and brain in odor perception, R. Axel and L. Buck have received the 2004 Nobel Prize for Medicine or Physiology. The picture shows schematically the coding of different odors in the olfactory epithelium (OE) and olfactory bulb (OB).

    5. Templated Growth of Metal–Organic Coordination Chains at Surfaces (pages 6142–6145)

      Thomas Classen, Guido Fratesi, Giovanni Costantini, Stefano Fabris, Frank Louis Stadler, Cheolkyu Kim, Stefano de Gironcoli, Stefano Baroni and Klaus Kern

      Article first published online: 20 SEP 2005 | DOI: 10.1002/anie.200502007

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      Line them up: Metal–organic chains (see scanning tunneling microscopy image) have been created in situ by self-organized growth at a metal surface under ultrahigh vacuum. These 1D arrangements of metal centers (Fe, Cu), regularly spaced by organic linkers such as trimesitylic acid, open new possibilities for the study of low-dimensional magnetism.

    6. Divergent Mechanisms for the Skeletal Rearrangement and [2+2] Cycloaddition of Enynes Catalyzed by Gold (pages 6146–6148)

      Cristina Nieto-Oberhuber, Salomé López, M. Paz Muñoz, Diego J. Cárdenas, Elena Buñuel, Cristina Nevado and Antonio M. Echavarren

      Article first published online: 7 SEP 2005 | DOI: 10.1002/anie.200501937

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      Support for the direct route: That cyclobutenes are not necessary intermediates in the skeletal rearrangement of enynes is supported by DFT calculations and kinetic studies. Cyclobutenes may arise from the corresponding syn-cyclopropylgold(I) carbenes (see scheme).

    7. Real-Time Observation of Ionization-Induced Hydrophobic[RIGHTWARDS ARROW]Hydrophilic Switching (pages 6149–6151)

      Shun-ichi Ishiuchi, Makoto Sakai, Yuji Tsuchida, Akihiro Takeda, Yasutake Kawashima, Masaaki Fujii, Otto Dopfer and Klaus Müller-Dethlefs

      Article first published online: 30 AUG 2005 | DOI: 10.1002/anie.200501430

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      That's quite a switch! The ionization-induced switch in the preferred intermolecular binding motif of the phenol⋅⋅⋅Ar interaction from π bonding to hydrogen bonding (see picture) has been monitored in real time by time-resolved picosecond UV-UV-IR pump-probe spectroscopy. The timescale for this prototypical intermolecular hydrophobic[RIGHTWARDS ARROW]hydrophilic (π[RIGHTWARDS ARROW]H) isomerization process (10 ps) has been measured for the first time.

    8. SOLARIA: A Protocol for Automated Cross-Peak Assignment and Structure Calculation for Solid-State Magic-Angle Spinning NMR Spectroscopy (pages 6151–6154)

      Michele Fossi, Federica Castellani, Michael Nilges, Hartmut Oschkinat and Barth-Jan van Rossum

      Article first published online: 20 SEP 2005 | DOI: 10.1002/anie.200501884

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      The liquid–solid transition: Automatic assignment of solid-state NMR data as well as fast and accurate calculation of the structure of immobilized proteins at atomic resolution can be achieved by using the program SOLARIA (a modification of the ARIA protocol). The picture shows the lowest energy structures of the α-spectrin SH3 domain calculated by SOLARIA (blue) overlaid with the X-ray crystal structure (red).

    9. AFM Snapshots of Synthetic Multifunctional Pores with Polyacetylene Blockers: Pseudorotaxanes and Template Effects (pages 6154–6157)

      Jiro Kumaki, Eiji Yashima, Guillaume Bollot, Jiri Mareda, Svetlana Litvinchuk and Stefan Matile

      Article first published online: 26 AUG 2005 | DOI: 10.1002/anie.200501886

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      Caught in a barrel: AFM studies indicate that the host–guest complexes formed between β-barrel pores and polymer blockers are pseudorotaxanes. The nonstatistical location of the contracted supramolecular barrels on the polymers indicates that the sticky polymer templates insert quickly into the β barrels (see schematic representation) and then undergo slow motion through the barrels.

    10. Rapid Two-Directional Synthesis of the F–J Fragment of the Gambieric Acids by Iterative Double Ring-Closing Metathesis (pages 6157–6162)

      J. Stephen Clark, Marc C. Kimber, Jerod Robertson, Christopher S. P. McErlean and Claire Wilson

      Article first published online: 31 AUG 2005 | DOI: 10.1002/anie.200501925

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      D-glucal is the starting point for the efficient synthesis of the F–J fragment of the gambieric acids (see scheme). The H-ring diol was subjected to double two-directional alkynyl ether formation, carbocupration ring-closing metathesis, and hydroboration. The tricyclic G–I diol was then converted into the F–J fragment by a sequence that involves another double two-directional ring-closing metathesis reaction.

    11. Direct Synthesis of a Thiolato-S and Sulfinato-S CoIII Complex Related to the Active Site of Nitrile Hydratase: A Pathway to the Post-Translational Oxidation of the Protein (pages 6162–6165)

      Emilie Bourles, Rodolphe Alves de Sousa, Erwan Galardon, Michel Giorgi and Isabelle Artaud

      Article first published online: 1 SEP 2005 | DOI: 10.1002/anie.200500814

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      Cyclic pseudopeptidic thiosulfinates reveal a new type of reaction that may be important in biological systems. It involves hydrolytic cleavage of the S(O)[BOND]S bond on 1 followed by metalation to form a dissymmetrical CoIII complex with a mixed diamidato-N, thiolato-S, sulfinato-S donor set in 2 that is related to the nitrile hydratase active site.

    12. Tetraarylphosphonium Halides as Arylating Reagents in Pd-Catalyzed Heck and Cross-Coupling Reactions (pages 6166–6169)

      Lee Kyoung Hwang, Youngim Na, Junseong Lee, Youngkyu Do and Sukbok Chang

      Article first published online: 20 SEP 2005 | DOI: 10.1002/anie.200501582

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      Highly efficient: Tetraarylphosphonium halides, Ar4P+X, as arylating reagents efficiently deliver an aryl group in Pd-catalyzed reactions with olefins, organoboron compounds, and terminal alkynes (see scheme).

    13. Highly Diastereoselective Alkylation of Aziridine-2-carboxylate Esters: Enantioselective Synthesis of LFA-1 Antagonist BIRT-377 (pages 6169–6172)

      Aniruddha P. Patwardhan, V. Reddy Pulgam, Yu Zhang and William D. Wulff

      Article first published online: 24 AUG 2005 | DOI: 10.1002/anie.200500923

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      The benzhydryl group is the key: Efficient alkylation of 3-substituted aziridine-2-carboxylates is only possible with N-benzhydryl-protected aziridines and occurs with complete retention of the configuration at the 2-position. Sequential catalytic asymmetric aziridination and aziridine alkylation reactions have been applied to the synthesis of BIRT-377 (see structure).

      Corrected by:

      Corrigendum: Highly Diastereoselective Alkylation of Aziridine-2-carboxylate Esters: Enantioselective Synthesis of LFA-1 Antagonist BIRT-377

      Vol. 44, Issue 47, 7661, Article first published online: 28 NOV 2005

    14. General Catalysts for the Suzuki–Miyaura and Sonogashira Coupling Reactions of Aryl Chlorides and for the Coupling of Challenging Substrate Combinations in Water (pages 6173–6177)

      Kevin W. Anderson and Stephen L. Buchwald

      Article first published online: 12 AUG 2005 | DOI: 10.1002/anie.200502017

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      Amphiphilic phosphine ligands (see structures; Cy=cyclohexyl) were prepared and utilized in palladium-catalyzed Suzuki–Miyaura and Sonogashira coupling reactions in water or water/organic biphasic solvents, providing excellent yields of functionalized biaryls and aryl alkynes, respectively.

    15. Dynamic Kinetic Resolution of α,β-Unsaturated Lactones through Asymmetric Copper-Catalyzed Conjugate Reduction: Application to the Total Synthesis of Eupomatilone-3 (pages 6177–6180)

      Matthew P. Rainka, Jacqueline E. Milne and Stephen L. Buchwald

      Article first published online: 30 AUG 2005 | DOI: 10.1002/anie.200501890

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      Only six steps were needed for the total synthesis of eupomatilone-3 in 48 % overall yield thanks to the development of a dynamic kinetic resolution that allowed the reductive conversion of a racemic α,β-unsaturated butenolide in high yield and high enantiomeric and diastereomeric excess. This copper-catalyzed dynamic kinetic resolution was then applied to several γ-aryl-containing α,β-unsaturated butenolides.

    16. High Thermal Stability Imparted by a Designed Tandem Arg–Trp Stretch in an α-Helical Coiled Coil (pages 6180–6183)

      Yuuki Sakurai, Toshihisa Mizuno, Hidekazu Hiroaki, Keigo Gohda, Jun-ichi Oku and Toshiki Tanaka

      Article first published online: 26 AUG 2005 | DOI: 10.1002/anie.200500806

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      Let's twist again: A cation–π interaction between Trp and Arg is designed at the interface between two α helices of a coiled-coil structure and stabilizes the structure more than Glu and Lys ion-pair interactions. Two or three Trp–Arg sets form an extended array of interactions (see picture) and increase the melting temperature of the peptide.

    17. Tin-Free Radical Carbonylation: Thiol Ester Synthesis Using Alkyl Allyl Sulfone Precursors, Phenyl Benzenethiosulfonate, and CO (pages 6183–6186)

      Sangmo Kim, Sunggak Kim, Noboru Otsuka and Ilhyong Ryu

      Article first published online: 31 AUG 2005 | DOI: 10.1002/anie.200501606

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      Remove contents from tin … Thiol esters have been successfully synthesized through tin-free radical carbonylation (see scheme; V-40=initiator). This approach can be further extended to sequential radical reactions involving cyclization, carbonylation, and trapping of acyl radicals by phenyl benzenethiosulfonate.

    18. Lewis Acid Catalyzed Asymmetric Cycloadditions of Nitrones: α′-Hydroxy Enones as Efficient Reaction Partners (pages 6187–6190)

      Claudio Palomo, Mikel Oiarbide, Elena Arceo, Jesús M. García, Rosa López, Alberto González and Anthony Linden

      Article first published online: 1 SEP 2005 | DOI: 10.1002/anie.200502308

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      A fine pair: Excellent levels of regio-, endo/exo-, diastereo-, and/or enantioselectivity are attained in the Cu-catalyzed cycloaddition of nitrones with α′-hydroxy enones (see scheme). The resulting adducts can be further elaborated to the corresponding isoxazolidines bearing aldehyde, ketone, and carboxylic acid functions.

    19. Tandem Radical-Addition–Aldol-Type Reaction of an α,β-Unsaturated Oxime Ether (pages 6190–6193)

      Masafumi Ueda, Hideto Miyabe, Hisako Sugino, Okiko Miyata and Takeaki Naito

      Article first published online: 26 AUG 2005 | DOI: 10.1002/anie.200502263

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      The direct generation of boryl enamine 2 by radical addition to the chiral α,β-unsaturated oxime ether 1 (X=(1R)-camphorsultam, Bn=benzyl) followed by reaction with aldehydes gave rise to a tandem carbon–carbon bond-forming method, yielding lactones 3. The result is a novel asymmetric synthesis of γ-butyrolactones and γ-amino acids by way of both a radical and an ionic process.

    20. Versatile Hypervalent-Iodine(III)-Catalyzed Oxidations with m-Chloroperbenzoic Acid as a Cooxidant (pages 6193–6196)

      Toshifumi Dohi, Akinobu Maruyama, Misaki Yoshimura, Koji Morimoto, Hirofumi Tohma and Yasuyuki Kita

      Article first published online: 25 AUG 2005 | DOI: 10.1002/anie.200501688

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      A new and effective use of hypervalent iodine(III) reagents as catalysts involves the transformation of iodoarenes 1 into hypervalent iodine(III) species 2 with meta-chloroperbenzoic acid (mCPBA) as the appropriate cooxidant. With observed turnover numbers greater than 70, this procedure paves the way for broader application of these useful oxidants in organic synthesis.

    21. Small Cyclopolyphosphinophosphonium Cations: Systematic Development of Fundamental catena-Phosphorus Frameworks (pages 6196–6199)

      Neil Burford, C. Adam Dyker, Mike Lumsden and Andreas Decken

      Article first published online: 31 AUG 2005 | DOI: 10.1002/anie.200501850

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      Methylation or phosphenium insertion reactions with cyclopolyphosphines (PtBu)3 or (PCy)4 (Cy=cyclohexyl) are presented as stereospecific and high-yielding preparative approaches to cyclopolyphosphinophosphonium cations. The cations [(PtBu)3Me]+, [(PCy)4Me]+, and [(PtBu)3PMe2]+ (see picture; P orange, C gray) are prepared as trifluoromethanesulfonate salts and represent key frameworks in fundamental catena-phosphorus chemistry.

    22. Optical Absorption and Structure of a Highly Symmetrical Neptunium(V) Diamide Complex (pages 6200–6203)

      Guoxin Tian, Jide Xu and Linfeng Rao

      Article first published online: 30 AUG 2005 | DOI: 10.1002/anie.200501281

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      A reflection on neptunium absorption: The absorption spectrum of NpV around 980 nm originates from a 5f[RIGHTWARDS ARROW]5f electric-dipole transition, which is allowed if the NpV ion lies in a coordination environment that lacks a center of inversion, such as in [NpO2(H2O)5]+. However, the transition is completely forbidden by Laporte's rule in the highly symmetrical NpV diamide complex [NpO2(L)2]+ (see structure; Np green, O red, N blue, C gray).

    23. On the Mechanism of the Reaction of Organic Azides with Transition Metals: Evidence for Triplet Nitrene Capture (pages 6203–6207)

      Mahdi M. Abu-Omar, Catherine E. Shields, Nicola Y. Edwards and Rebecca A. Eikey

      Article first published online: 29 AUG 2005 | DOI: 10.1002/anie.200462647

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      High-valent imido complexes are obtained by reaction of the manganese(III) corrole [Mn(tpfc)] with aryl azides by a novel reaction mechanism in which singlet nitrene undergoes intersystem crossing to the triplet state, which is trapped by the metal corrole, in competition with dimerization to the azo compound (see scheme).

    24. Single-Molecule Studies of Electronic Energy Transfer in a Diblock Conjugated Polymer (pages 6207–6210)

      John K. Grey, Doo Young Kim, Young Jong Lee, Jose J. Gutierrez, Nam Luong, John P. Ferraris and Paul F. Barbara

      Article first published online: 1 SEP 2005 | DOI: 10.1002/anie.200501388

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      Energy transfer at the interface of two dissimilar conjugated polymer chains (see picture; DMOS=2-dimethyloctylsilyl-p-phenylenevinylene; MEH=2-methoxy-5-(2′-ethylhexyloxy)-p-phenylenevinylene) has been studied using single-molecule spectroscopy. Morphological features control energy-transfer processes between the blocks and lead to strongly heterogeneous efficiencies of energy transfer.

    25. 2-Deoxyribonolactone Lesions in X-ray-Irradiated DNA: Quantitative Determination by Catalytic 5-Methylene-2-furanone Release (pages 6210–6213)

      Marina Roginskaya, Yuriy Razskazovskiy and William A. Bernhard

      Article first published online: 1 SEP 2005 | DOI: 10.1002/anie.200501956

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      Torn genes: DNA tetramers containing the 2-deoxyribonolactone (dL) lesion have been isolated by HPLC from d(CGCG) and d(pCGCG) films irradiated with X-rays. Upon treatment with spermine as a catalyst, the dL-containing tetramers decompose to 5-methylene-2-furanone (5-MF; see scheme), a characteristic product of dL decomposition. Hence, 5-MP can be used to quantify dL lesions in DNA.

    26. Ruthenium(II) Terdentate CNN Complexes: Superlative Catalysts for the Hydrogen-Transfer Reduction of Ketones by Reversible Insertion of a Carbonyl Group into the Ru[BOND]H Bond (pages 6214–6219)

      Walter Baratta, Giorgio Chelucci, Serafino Gladiali, Katia Siega, Micaela Toniutti, Matteo Zanette, Ennio Zangrando and Pierluigi Rigo

      Article first published online: 1 SEP 2005 | DOI: 10.1002/anie.200502118

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      Very low loading and short reaction times are characteristic features of the quantitative reduction of different ketones using 2-propanol and terdentate [RuX(CNN)(dppb)] (X=H, Cl (see structure); dppb=Ph2P(CH2)4PPh2) complexes prepared from 6-(4′-methylphenyl)-2-pyridylmethylamine. The reduction apparently takes place by reversible insertion of the substrate into the Ru[BOND]H bond, thus leading to a RuII alkoxide.

    27. Organocatalytic Asymmetric α-Halogenation of 1,3-Dicarbonyl Compounds (pages 6219–6222)

      Giuseppe Bartoli, Marcella Bosco, Armando Carlone, Manuela Locatelli, Paolo Melchiorre and Letizia Sambri

      Article first published online: 1 SEP 2005 | DOI: 10.1002/anie.200502134

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      No metal required: A protocol for the enantioselective organocatalytic chlorination of cyclic and acyclic β-keto esters and cyclic β-diketones has been developed which is also effective for the asymmetric bromination of β-keto esters. The methodology employs an inexpensive organocatalyst (e.g. benzoylquinidine) and polyhalogenated quinolinones as the source of the halogen (see scheme).

      Corrected by:

      Corrigendum: Organocatalytic Asymmetric α-Halogenation of 1,3-Dicarbonyl Compounds

      Vol. 45, Issue 3, 340, Article first published online: 5 JAN 2006

    28. Structural Dualism in the Zwitterionic 7-RR′NH-nido-7,8,9-C3B8H10 Tricarbollide Series: An Example of Absolute Tautomerism (pages 6222–6226)

      Mario Bakardjiev, Josef Holub, Drahomír Hnyk, Ivana Císařová, Michael G. S. Londesborough, Dmitry S. Perekalin and Bohumil Štíbr

      Article first published online: 11 AUG 2005 | DOI: 10.1002/anie.200501018

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      The dual in the crown: The same compound can adopt two different, non-equilibrium tautomeric structures. This unique structural dualism is demonstrated by the isolation of pure tautomeric pairs, 7-RR′NH-7,8,9-C3B8H10 (zwitterionic) and 7-RR′N-7,8,9-C3B8H11 (neutral) (where R,R′=H or alkyls, see scheme, PNT=proton nontransferring, PT=proton transferring) in the tricarbollide series.

    29. Synthesis of Enantiopure Carbohydrate Mimetics by Lewis Acid Catalyzed Rearrangement of 1,3-Dioxolanyl-Substituted 1,2-Oxazines (pages 6227–6231)

      Ahmed Al-Harrasi and Hans-Ulrich Reißig

      Article first published online: 14 SEP 2005 | DOI: 10.1002/anie.200501127

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      Under control: Lewis acids induce an unexpected rearrangement of 1,3-dioxolanyl-substituted 1,2-oxazines to provide bicyclic compounds in a stereocontrolled manner. They are precursors for enantiopure carbohydrate mimetics containing 3-aminotetrahydropyran or 4-aminooxepane substructures (see scheme; Bn=benzyl).

    30. A General Sultone Route to the Pamamycin Macrodiolides—Total Synthesis of Pamamycin-621A and Pamamycin-635B (pages 6231–6234)

      Petra Fischer, Ana Belén García Segovia, Margit Gruner and Peter Metz

      Article first published online: 7 SEP 2005 | DOI: 10.1002/anie.200501511

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      Sultones swing again: The first total syntheses of the title antibiotics (see scheme) were achieved by application of sultone methodology. Since the final lactonizations with formation of the ester linkage between C1′ and the oxygen substituent on C8 proceeded with complete epimerization at C2′, the more readily available C2′ epimeric smaller fragments could be used for streamlining the synthetic sequence.

    31. Activation of a Zinc-Bound Ethyl Group by Formation of a Zn-CEt-Ba Moiety and Crystal Structure of [{(Me3Si)2N}Ba(thf)Zn2(μ-Et)(μ3-PSitBu3)2]2 with Bridging Ethyl Substituents (pages 6234–6237)

      Matthias Westerhausen, Gerhard Sapelza and Peter Mayer

      Article first published online: 7 SEP 2005 | DOI: 10.1002/anie.200501899

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      The phosphane unit is deprotonated in the reaction of dialkylzinc with H2PSitBu3 and (thf)2Ba[N(SiMe3)2]2 to give the title compound (molecular structure shown), which has a coordinatively unsaturated barium center. In the absence of excess THF, the zinc-bound alkyl groups are activated by formation of Ba-CEt-Zn three-center bonds.

    32. Metal@MOF: Loading of Highly Porous Coordination Polymers Host Lattices by Metal Organic Chemical Vapor Deposition (pages 6237–6241)

      Stephan Hermes, Marie-Katrin Schröter, Rochus Schmid, Lamma Khodeir, Martin Muhler, Arno Tissler, Richard W. Fischer and Roland A. Fischer

      Article first published online: 30 AUG 2005 | DOI: 10.1002/anie.200462515

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      Precursors and particles captured in a net: Porous coordination polymers such as MOF-5 are efficient gas storage devices and are also able to absorb metal organic chemical vapor deposition (MOCVD) precursors (see picture, red: [(η5-C5H5)Pd(η3-C3H5)]). These incorporated compounds are easily reduced to give the corresponding metal nanoparticles. Applications in heterogeneous catalysis, for instance, methanol synthesis or hydrogenation, are described.

    33. Synthesis and Molecular Structure of the Cu4P8 Cage Compound [Cu4(P4Ph4)2(PCyp3)3] (pages 6241–6244)

      Robert Wolf and Evamarie Hey-Hawkins

      Article first published online: 7 SEP 2005 | DOI: 10.1002/anie.200501607

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      Plenty of phosphorus: The first CuI oligophosphanido complex [Cu4(P4Ph4)2(PCyp3)3] (1; Cyp=cyclo-C5H9), synthesized from [CuCl(PCyp3)2] and [Na2(thf)4(P4Ph4)], displays a remarkable cage structure in the solid state. The central Cu4P8 core of 1 (with appendant phosphane P atoms) is shown in the picture.

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      Preview: Angew. Chem. Int. Ed. 38/2005 (page 6251)

      Article first published online: 20 SEP 2005 | DOI: 10.1002/anie.200590129

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