Angewandte Chemie International Edition in English

Cover image for Vol. 28 Issue 3

March 1989

Volume 28, Issue 3

Pages 253–396

Currently known as: Angewandte Chemie International Edition

    1. Cover Picture (Angew. Chem. Int. Ed. Engl. 3/1989)

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198902531

      Thumbnail image of graphical abstract

      The cover picture shows interpenetrating pagodane (orange) and dodecahedrane (blue) frameworks–as illustration of the pagodane route to dodecahedranes. That pagodane can be catalytically isomerized to the C20H20 hydrocarbon was already known. New are the possibilities of synthesizing four-,six- and eightfold functionalized dodecahedranes. Unsaturated dedecahedranes modified with additional framework atoms are also accessible. The planning of the syntheses was facilitated by MM2 force field calculations. Further details of these fascinating cage compounds and their elegant syntheses are reported on by H. Prinzbach et al. in a series of communications starting on page 298. Cover illustration: Dr. Lothar Knothe.

  1. Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    5. Editorial Essay
    6. Reviews
    7. Research News
    8. Book Reviews
    9. Conference Calendar
    1. Stiff-Chain Polymers—Structure, Phase Behavior, and Properties (pages 253–267)

      Dr. Matthias Ballauff

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198902533

      The unusual mechanical properties of stiff-chain polymers have aroused increasing interest in recent years. High modulus fibers and moldings can be fabricated from these polymers, which usually exhibit an exceedingly low solubility or are absolutely insoluble and do not melt. These properties are directly related to the nearly parallel arrangement of the rodlike molecules in the solid state, which is achieved through spinning or extrusion from a liquid crystalline (nematic) state. It is therefore evident that a thorough understanding of phase behavior and the structure is required for a universal technical utilization of these materials.

    2. Theoretical Chemistry en route to a Theory of Chemistry (pages 268–276)

      Dr. Anton Amann and Dr. Werner Gans

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198902681

      Fractals, chaotic motion, quasicrystals, and knot theory, these are the key words summarizing other approaches which have established themselves independently of algebraic quantum mechanics for the theoretical treatment of chemical problems. They are suitable, for example, for describing the phase transitions in dilute magnets and the gelation of polymers, the spectra of systems with strongly coupled degrees of freedom, the structure of certain intermetallic phases, and the knotting in DNA molecules.

    3. The Structure of Lithium Compounds of Sulfones, Sulfoximides, Sulfoxides, Thioethers and 1,3-Dithianes, Nitriles, Nitro Compounds and Hydrazones (pages 277–297)

      Prof. Dr. Gernot Boche

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198902771

      Thumbnail image of graphical abstract

      The marked discrepancy between the importance of compound in organic synthesis and a knowledge of its structure was, until quite recently, characteristic for the title compounds. However, since we have learned to exploit them in chemo-, regio-, diastereo- and enantioselective reactions, interest in their structure, especially their solid-state structures, has increased tremendosuly. For lithium compounds of type LiA-CRR′ (A = acceptor), the sulfoxide [Ph(Me)CS(Ph)O]- Li is chosen as example. It crystallizes as the dimer 1 with TMEDA and forms an Li[BOND]O[BOND]Li[BOND]O ring.

  2. Communications

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    5. Editorial Essay
    6. Reviews
    7. Research News
    8. Book Reviews
    9. Conference Calendar
    1. The Pagodane Route to Dodecahedranes: Chemistry and Structure of Bissecododecahedranes (pages 298–300)

      Dipl.-Chem. Georg Lutz, Dr. Dieter Hunkler, Prof. Dr. Horst Prinzbach and Grety Rihs

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198902981

      Thumbnail image of graphical abstract

      An insight into the chemistry of dodecahedranes necessitates access to singly and multiply functionalized derivatives in preparative amounts. The first way failed: several bisseco precursors, including the di- and tetra-substituted derivatives 1 and 2 and the diones 3–5 have been obtained but could not be dehydrogenated to dodecahedrane derivatives.

    2. The Pagodane Route to Dodecahedranes: Total Synthesis and Chemistry of 4,9,14,19-Tetrasubstituted [1.1.1.1]Pagodanes (pages 300–303)

      Dipl.-Chem. Johann-Peter Melder, Prof. Dr. Hans Fritz and Prof. Dr. Horst Prinzbach

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903001

      Thumbnail image of graphical abstract

      The tetraketone 1 and the dimethoxydiketone 2, R = CH3, could prove to be important intermediates en route to dodecahedranes. They can be prepared in several steps in good yield from 7-tert-butoxynorbornadiene and tetrachlorocyclopentadienone dimethyl ketal. According to force field calculations the four sp2-hybridized C atoms in 1 should facilitate thermal cleavage of the central four-membered ring and a subsequent hydrogenation.

    3. The Pagodane Route to Dodecahedranes: 4,9,14,19-Tetrasubstituted [1.1.1.1]Pagodanes by Intramolecular Functionalization (pages 303–305)

      Dipl.-Chem. Rolf Pinkos, Prof. Dr. Horst Prinzbach and Grety Rihs

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903031

      Thumbnail image of graphical abstract

      The highly efficient double intramolecular Barton functionalization of the syn, syn-diamide 1, accessible in gram amounts, to 2 is a decisive step of the dodecahedrane synthesis at Freiburg University. Directed epimerizations, which are probably important for the subsequent C[BOND]C couplings, are partly possible by exploiting neighboring group effects.

    4. The Pagodane Route to Dodecahedranes: Polyfunctionalized Pentagonal Dodecahedranes and Dodecahedrenes (pages 305–310)

      Dipl.-Chem. Johann-Peter Melder, Dipl.-Chem. Rolf Pinkos, Prof. Dr. Hans Fritz and Prof. Dr. Horst Prinzbach

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903051

      Thumbnail image of graphical abstract

      The four-, six-, and eightfold symmetrically functionalized dodecahedranes 1-4 have been synthesized via the “pagodane route”. Particularly helpful in the planning of the syntheses were MM2 force field calculations.

    5. The Pagodane Route to Dodecahedranes: Polyfunctionalized Homologous Dodecahedranes and Dodecahedrenes (pages 310–313)

      Dipl.-Chem. Rolf Pinkos, Dipl.-Chem. Johann-Peter Melder, Prof. Dr. Hans Fritz and Prof. Dr. Horst Prinzbach

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903101

      Thumbnail image of graphical abstract

      The spherical structure of dodecahedranes can be varied by replacing the individual CC moieties of the skeleton by C(O)C groups. This enabled the synthesis of the highly symmetric diolefin 1, whose small π/π* distance manifests itself, inter alia, in a long wavelength UV absorption. The more severely strained diene 2 could not by prepared.

    6. Do Any ABn Molecules Have Anomalous Shapes? v3 of TiF4 and TiF3 and Their Relevance to the Shape of TiF2 (pages 313–315)

      Prof. Ian R. Beatte, Peter J. Jones and Dr. Nigel A. Young

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903131

      There is no firm evidence that any first row transition element dihalides are non-linear. This conclusion is drawn from the fact the IR bands previously assigned to “non-linear” LiF2 definitely arise from trigonal planar TiF3. Earlier matrix isolation studies, from which a 120°-TiF2 had been concluded, formed the cornerstone of the theory of anomalous MF2 molecules.

    7. tBu2P[BOND]P[DOUBLE BOND]PbrtBu2. LiBr and the Formation of tBu2P[BOND] (pages 315–316)

      Prof. Dr. Gerhard Fritz, Dr. Tilo Vaahs, Dipl.-Chem. Holm Fleischer and Dr. Eberhard Matern

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903151

      Thumbnail image of graphical abstract

      Clear indications of the formation of diphosphanediyl tBuP[BOND]

      in the thermal decomposition of 1 are the products 2 and 3 as well as those of trapping reactions with 2,3-dimethyl-1,3-butadiene and cyclohexene 4/5 and 6, respectively.

    8. [M(NMesBMes2)2] (M = Cr, Ni) : Stable, Distorted, Two-Coordinate d4 and d8 Complexes (pages 316–317)

      Ruth A. Bartlett, Hong Chen and Prof. Philip P. Power

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903161

      Thumbnail image of graphical abstract

      The structures of the two title complexes are surprisingly different: The chromium complex 1 has an angular (ca. 112°) and the nickel complex an almost linear (ca. 168°) N[BOND]M[BOND]N arrangement. The two complexes can be prepared from LiNMesBMes2 and [CrCl2(thf)2] or NiBr2·5/3THF, respectively. The angular arrangement in 1 is presumably due to a widening of the Cr coordination by Cr[BOND]C contacts. Mes = 2,4,6-trimethylphenly.

    9. Two Ferrole Isomers in Equilibrium: Experimental Confirmation of an Old Hypothesis (pages 318–319)

      Dr. Miklos Tasi, Dr. Anne K. Powell and Prof. Dr. Heinrich Vahrenkamp

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903181

      Thumbnail image of graphical abstract

      The reversible interconversion of the two complexes 1a and 1b confirms the long predicted possibility of the isomerization of ferrole complexes. That this could be successfully demonstrated in the case of 1 may also be attributable to the fact that the complex component Fe(CO)3(N2Et2) leads to an electron density equalization in the ferrole unit, which facilitates flipping of the butadienediyl ligand.

    10. The 30-Electron Rule for Triple-Decker Complexes –Vanadium, Niobium and Tantalum Complexes as Illustrative Examples (pages 319–320)

      Prof. Dr. Gerhard E. Herberich, Dr. Ingeborg Hausmann and Dipl.-chem. Norbert Klaff

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903191

      Thumbnail image of graphical abstract

      Strong σ-donor-π-acceptor ligands as outer ligands should lead to 30 as optimum valence electron number for triple-decker complexes. This was confirmed by the synthesis of the light-sensitive complexes 1–4. Hitherto, in the case of niobium and tantalum no triple-decker complexes had been known, and in the case of vanadium only such complexes with 26 valence electrons (2, M = V; 3, M = Nb; 4, M = Ta).

    11. NaBH4 Reduction of Ketones in the Solid State (pages 320–321)

      Prof. Fumio Toda, Koji Kiyoshige and Minoru Yagi

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903201

      Thumbnail image of graphical abstract

      Without solvent, merely by rubbing the solid reactants in an agate mortar, it was possible to reduce more than just simple ketones with NaBH4; even regio- and enantioselective reductions could be achieved when inclusion complexes were used. The hydroxyketones 2 and 4, which are of interest as synthetic building blocks, were prepared from the ketones 1 and 3, respectively.

    12. Formation of a Phosphaferracyclopentadiene Ring by Coupling of a Phosphaalkyne with Two Fluoromethylidyne Ligands (pages 321–323)

      Priv.-Doz. Dr. Dieter Lentz and Dipl.-Chem. Heike Michael

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903211

      Thumbnail image of graphical abstract

      The pentagonal-bipyramidal closo-cluster 1 is the product of the reaction of tBu[BOND]C[TRIPLE BOND]P with [Fe3(CO)93-CF)2]. 1 contains an almost perfectly planar phosphaferracyclopentadiene moiety. According to the Wade rules 1 has a nonbonding pair of electrons on the phosphorus atom. Accordingly, with 16-electron fragments it forms stable complexes in which the cluster skeleton hardly changes.

    13. Microstructure of a Discotic Polymer as Revealed by Electron Diffraction and High-Resolution Imaging (pages 323–325)

      Dr. Ingrid Gisela Voigt-Martin, Heinz Durst, Volker Brzezinski, Herbert Krug, Dr. Willi Kreuder and Prof. Dr. Helmut Ringsdorf

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903231

      Thumbnail image of graphical abstract

      The arrangement of the columns in a liquid crystalline discotic polymer can be made visible by high resolution electron microscopy (see picture on the right). A two-dimensional hexagonal ordering of the columns is observed; specific packing defects can also be detected. These findings are supported by computer processing of the images.—The discotic polymer is formally a polyester of tetrakis(pentyloxy)triphenylenediol and hexadecanoic diacid.

    14. On the Formation of “Free Radicals” from Alkylcobalt Complexes (pages 325–327)

      Prof. Dr. Bernd Giese, Dipl.-Ing. Jens Hartung, Dipl.-Ing. Jianing He, Dipl.-Ing. Ottmar Hüter and Dipl.-Ing. Andreas Koch

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903251

      Thumbnail image of graphical abstract

      The photolysis of alkylcobaloximes such as 1 affords free radicals. This was deduced from reactivity and selectivity studies in which the intermediates generated from cobaloximes as well as via vitamin B12 behaved precisely as those from other radical sources. This finding is very important for the planning of syntheses and has implications for the discussions of vitamin B12-catalyzed reactions in living organisms. Hitherto, the general opinion was that radicals so generated are somewhat stronger bound to the cobalt complex (dmgH2 = 2,3-butanedionedioxime, py = pyridine).

    15. Correlation of the Dynamic Behavior of n-Alkyl Ligands of the Stationary Phase with the Retention Times of Paracelsin Peptides in Reversed Phase HPLC (pages 327–329)

      Dipl.-Chem. Betting Pfleiderer, Dr. Klaus Albert, Prof. Dr. Ernst Bayer, Dr. Klaus D. Lork, Prof. Dr. Klaus K. Unger and Prov.-Doz. Dr. Hans Brückner

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903271

      The retention behavior of sterically demanding molecules with defined conformation in reversed phase HPLC is strongly influenced by the mobility of the lipophilic alkyl chains of the stationary phase. This follows from a comparison of the T1pH values determined for the alkyl chains by CP/MAS 13C NMR spectroscopy as a measure of their mobility with the retention times of the four components of the natural mixture of paracelsin peptides, which are characterized by very stable helical conformations. The C4 phase was conformationally least mobile (smallest T1PH, 44.4 ms for the methyl-C) and exhibited the longest retention times.

    16. Much Less Strained Cubane Analogues with Si, Ge, Sn, and Pb Skeletons (pages 329–330)

      Prof. Shigeru Nagase

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903291

      Virtually strain-free four-membered rings are formed by the higher homologues of carbon, namely silicon, germanium, tin, and lead. This followed from ab initio calculations of the corresponding hetero-cubanes, -prismanes, and -tetrahedranes. In the case of carbon the cubane skeleton exhibits the strongest strain, whereas in the case of the other four elements it is always the least strained skeleton. Thus the strain energy of perplumbacubane is ca. 100 kcal−1 smaller than that of cubane. The X[BOND]X bonds of the cubanes are only ca. 0.02–0.04 Å longer than those of the cyclobutanes, and also the strain energies per ring are very similar in the case of the cubanes and cyclobutanes.

    17. Using Crystal Birefringence to Study Molecular Recognition (pages 330–333)

      Prof. J. Michael McBride and Steven B. Bertman

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903301

      Thumbnail image of graphical abstract

      That a growing crystal can discriminate between almost equally sized bromine atoms and CH3 groups can easily be demonstrated by light microscopy. Local birefringence of slightly impure crystals reflects their mechanism of growth. Merely a pair of polarization filters and a sensitive violet filter are required for the detection of the color effects (blue/yellow). Upon rotation through 90°, e.g., a crystal growing from the center shows the color change indicated on the right.

    18. Total Synthesis of the Antitumor Antibiotic WF-3161 (pages 333–334)

      Prof. Dr. Ulrich Schmidt, Dipl.-Chem. Ulrich Beutler and Dr. Albrecht Lieberknecht

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903331

      Thumbnail image of graphical abstract

      The cyclopeptide WF-3161 (2) counts among the most effective cytostatics in vitro.—After stereoselective synthesis of the linear Z-tetrapeptide pentafluorophenyl ester 1, the ring is subsequently closed (in 74% yield) by catalytic hydrogenation. Conversion of the chloroketal into an epoxyketone completes the synthesis of the natural product.

    19. Alkyl and Alkylidyne Complexes of Rhenium (pages 334–337)

      Josef K. Felixberger, Paul Kiprof, Dr. Eberhardt Herdtweck, Prof. Dr. Wolfgang A. Herrmann, Ralf Jakobi and Prof. Dr. Philipp Gütlich

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903341

      Thumbnail image of graphical abstract

      The multiplicity of its oxidation states enables the element rhenium to fix numerous ligand types in stable complexes. The synthesis of “Cp*ReClMe3” now completes the series of Rev complexes “Cp*ReClnMe4–n”. The neopentyl complex 1 reacts with C5H5TiCl3 to give the paramagnetic carbyne complex 2, which can be smoothly oxidized to the diamagnetic complex 3. Complexes 2 and 3 are the first π-cyclopentadienylcarbyne complexes with rhenium in high oxidation states (ReVI and ReVII, resp.). Cp* = η5-C5(CH3)5.

    20. Synthesis of O-Acetyl-N (4-biphenylyl)hydroxylamine (“N[BOND]Acetoxy-4-aminobiphenyl”), an Ultimate Metabolite of Carcinogenic 4-Aminobiphenyl, and Its Reaction with Deoxyguanosine (pages 337–338)

      Dipl.-Chem. Michael Famulok, Ferdinand Bosold and Prof. Dr. Gernot Boche

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903371

      Thumbnail image of graphical abstract

      The carcinogenicity of aromatic amines has been known since 1895. It has now been possible for the first time to convert the hydroxylamine derivative generated from 4-aminobiphenyl 1 into the crystalline title compound 2 in vitro. 2 reacts with deoxyguanosine to give the same “adducts” which, e.g., are also obtained when 1 is administered to dogs and the DNA is subsequently cleaved enzymatically (Aryl = 4-biphenylyl).

    21. Photochemical Formation of a Stable Oxalic Acid Orthoamide with a Propellane Structure (pages 338–339)

      Dr. Erich Tauer, Dr. Karl-Heinz Grellmann, Dr. Mathias Noltemeyer and Prof. George M. Sheldrick

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903381

      Thumbnail image of graphical abstract

      The first stable orthoamide of oxalic acid with the substitution pattern of a hexaaminoethane, the “4.4.4” propellane 2, was obtained by irradiation of 1 in cyclohexane (R = CH3).

    22. (tBuSiP)4–The First Silaphosphacubane (pages 339–341)

      Prof. Dr. Marianne Baudler, Guido Scholz, Prof. Dr. Karl-Friedrich Tebbea and Dr. Magda Fehér

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903391

      Thumbnail image of graphical abstract

      The title compound 1 contains a cubic array of four P and four Si atoms. This first silaphosphacubane is formed as a secondary product in the reaction of tBuSiCl3 with LiAl(PH2)4. It is probably formed by intermolecular condensation of functionalized Si-P four-membered rings, which are detectable 31P-NMR spectroscopically as intermediates. The Si4P4 cube, with bond angles of 102° at silicon and 77° at the phosphorus is severely distorted.

    23. A Novel Trimeric Chiral Copper(I) Thiophenolate with Intramolecular Coordination (pages 341–342)

      Drs. D. Martin Knotter, Prof. Dr. Gerard van Koten, Hendrik L. van Maanen, Dr. David M. Grove and Dr. Anthony L. Spek

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903411

      Thumbnail image of graphical abstract

      The crown-ether-like compound 1 contains an interesting, folded Cu3S3 ring: The S3 side is “open”, while the Cu3 side is shielded by the organic grounds. The chiral starting compound, 2-“(R)-1-(dimethylamino) ethyl” thiophenol, favors formation of the illustrated diastereomer. 1 shows intense (greenish) triboluminescence.

    24. (C4Me4NBH3)2Fe—a Metal Complex Isosteric with Decamethylferrocene with Characteristic Metallocene Disorder (pages 342–344)

      Prof. Dr. Norbert Kuhn, Dipl.-Chem. Eva-Maria Horn, Dr. Roland Boese and Dipl.-Chem. Norbert Augart

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903421

      Thumbnail image of graphical abstract

      An acentric coordination of the trihydro(tetramethylpyrrolyl) borato ligand in 1 is effected by the “small” nitrogen atom. Like the isosteric decamethylferrocene, 1 is disordered by shifting and rotation of the C5 axis in the crystal. The novel ligand of 1 could be incorporated at the Fe center of the analogous “boron-free” complex with Me2S·BH3.

    25. Structural Diversity in Iodoantimonates; the Anions Sb3Imath image, Sb5Imath image and Sb6Imath image (pages 344–345)

      Prof. Dr. Siegfried Pohl, Dipl.-Chem. Rainer Lotz, Dipl.-Chem. Wolfgang Saak and Dipl.-Ing. Detlev Haase

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903441

      Thumbnail image of graphical abstract

      An unusual tailoring to the “spatial requirements” of the cation in a crystal is observed with iodoantimonate(III) anions. This is demonstrated by the synthesis of the salts [Cu(MeCN)4]2[Sb3I11], [Me4N]3[Sb5I18] and [Cp2Fe]4[Sb6I22]from SbI3 and the corresponding iodide.

    26. Synthesis and Structure of a Binuclear syn-Coordinated μ-Cycloheptatrienyl Hydrido Complex with Hindered C7H7 Rotation (pages 345–347)

      Dr. Hubert Wadepohl, Dipl.-Chem. Wolfgang Galm and Dr. Hans Pritzkow

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903451

      Thumbnail image of graphical abstract

      The rotation of the C7H7, bridge ligand of 1 is already frozen-in on the NMR time scale. 1 is the first syn-μ-cycloheptatrienyl complex in which this has been observed. It also contains the first CrHCo bridge to be structurally analyzed, which has bond lengths of 1.69 and 1.54 Å and subtends an angle of 127°.

    27. Selective Hydrogenation of Esters to Alcohols with a Catalyst Prepared from Rh2O3, Sn(n-C4H9)4, and SiO2: Evidence for Site Isolation (pages 347–349)

      Dr. Abdellah El Mansour, Dr. Jean P. Candy, Dr. Jean P. Bournonville, Dr. Osmar A. Ferretti and Dr. Jean-Marie Basset

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903471

      Thumbnail image of graphical abstract

      A cooperation of neighboring rhodium atoms in catalysis is prevented by the incorporation of tin atoms into the surface of an SiO2-supported rhodium catalyst in accord with equation (a). This manifests itself for example in the absence (IR) of bridged CO ligands after chemisorption of CO on the Rh/Sn/SiO2 catalyst, and leads to an increase in selectivity in the hydrogenation of ethyl acetate: The amount of ethanol increases from 57.2 (Sn/Rh = 0/1) to 97.2% (Sn/Rh = 1.7/1). At the same time the conversion of ethyl acetate increases from 1.32 to 4.66%.

    28. Flexible Syntheses of Optically Active Isocarbacyclins (pages 349–351)

      Dipl.-Chem. Horst Hemmerle and Prof. Dr. Hans-Joachim Gais

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903491

      Thumbnail image of graphical abstract

      The isocarbacyclins, e.g. 1, are potent and chemically stable analogues of the hemostase-regulator prostacyclin, the structure of the side chains of which is decisive for their biological activity. Key steps of the enantioselective syntheses described here for systems of type 1 are the radical cyclization to the bicyclo “3.3.0” octane skeleton and γ-substitutions for the attachment of “upper” side chains with introduction of the endocyclic double bond.

    29. Copper(I)-Promoted Michael-Addition Reaction of Organozincs of Esters, Nitriles, and α-Amino Acids (pages 351–353)

      Dr. Yoshinao Tamaru, Hiroto Tanigawa, Tetsuji Yamamoto and Prof. Zen-ichi Yoshida

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903511

      Thumbnail image of graphical abstract

      Exclusively 1,4-addition is observed in the reactions of β-, γ-, δ- and ϵ-(iodozinca)esters, -nitriles and -α-amino acids with α,β-unsaturated aldehydes, ketones and esters in the presence of HMPA, CuCN and Me3SiCl. This broadens the scope of application of the Michael addition to carbanions in which the carbanion center is separated by more than two carbon atoms from an electrophilic substituent. Thus, the ω-formylcarboxylate 3 is formed in 94% yield from 1 and the aldehyde 2.

  3. Book Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    5. Editorial Essay
    6. Reviews
    7. Research News
    8. Book Reviews
    9. Conference Calendar
    1. Book Review: From CA to CAS Online. By H. Schulz (page 356)

      James F. Sibley

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903561

  4. Editorial Essay

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    5. Editorial Essay
    6. Reviews
    7. Research News
    8. Book Reviews
    9. Conference Calendar
    1. European Materials Societies (pages 357–358)

      Dr. Robert Lallement

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903571

  5. Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    5. Editorial Essay
    6. Reviews
    7. Research News
    8. Book Reviews
    9. Conference Calendar
    1. Advanced Zeolite, Materials Science (pages 359–376)

      Prof. Geoffrey A. Ozin, Alex Kuperman and Andreas Stein

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903591

  6. Research News

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    5. Editorial Essay
    6. Reviews
    7. Research News
    8. Book Reviews
    9. Conference Calendar
    1. Ferroelectricity and Superconductivity (pages 379–380)

      Helmut Büttner and A. Bussmann-Holder

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903791

  7. Book Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    5. Editorial Essay
    6. Reviews
    7. Research News
    8. Book Reviews
    9. Conference Calendar
    1. Book Review: Semiconductor Electrodes. Edited by H. O. Finklea (pages 386–387)

      Hans-Joachim Lewerenz

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903861

  8. Conference Calendar

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    5. Editorial Essay
    6. Reviews
    7. Research News
    8. Book Reviews
    9. Conference Calendar
    1. Conference Calendar (pages 388–396)

      Version of Record online: 30 DEC 2003 | DOI: 10.1002/anie.198903881

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