Angewandte Chemie International Edition in English

Cover image for Vol. 24 Issue 7

June 1985

Volume 24, Issue 7

Pages 529–616

Currently known as: Angewandte Chemie International Edition

    1. Cover Picture (Angew. Chem. Int. Ed. Engl. 7/1985)

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505291

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      The cover page shows the—simplified—crystal structure of a new carbene complex which consists of an oxazirconaindanylidene fragment and a W(CO)5 fragment. The picture shows (upper row, left to right) the (OC)[BOND]W[BOND](C3O)Zr units; the bonds from zirconium to the two cyclopentadienyl ligands are shown as “spikes”. In the solid state, the polymeric, helical structure is stabilized by solvent molecules (here toluene). Not only the structure, but also the one-step synthesis of the complex via a dehydrobenzene derivative of zirconocene is unusual. Further details are reported by G. Erker et al. on page 584.

  1. Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    1. Consequences of Strain for the Structure of Aliphatic Molecules (pages 529–538)

      Prof. Dr. Christoph Rüchardt and Dr. Hans-Dieter Beckhaus

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505293

      Structureal parameters and preferred conformations of highly substituted ethanes 1 and 2 can be reliably calculated by the force field method. In 2, the substituents can evade mutual repulsion by enlargement of the R1[BOND]C[BOND]R2 angle, whereas in 1 the central C[BOND]C bond must be elongated for this purpose.

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    2. Chiral Compounds Synthesized by Biocatalytic Reductions [New Synthetic Methods (51)] (pages 539–553)

      Prof. Dr. Helmut Simon, Dr. Johann Bader, Dr. Helmut Günther, Dr. Stefan Neumann and Dr. Jordanes Thanos

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505391

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      The combination of enzyme chemistry and electrochemistry opens up a promising route to stereoselective reactions. Particularly useful are two novel reductases which do not require pyridine nucleotides and take up electrons directly from reduced methylviologen (MV⊕⊙), which is regenerated electrochemically.

    3. Syntheses with Radicals—C[BOND]C Bond Formation via Organotin and Organomercury Compounds [New Synthetic Methods (52)] (pages 553–565)

      Prof. Dr. Bernd Giese

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505531

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      The addition of radicals to alkenes provides new possibilities in preparative organic chemistry. Prerequisite is that the adduct-radical can be trapped with H-donors (R3SnH, RHgH) before polymerization and that the reaction proceeds as a radical chain reaction. An example is the addition of the radical generated from 1 to acrylonitrile in the presence of Bu3SnH.

  2. Communications

    1. Top of page
    2. Reviews
    3. Communications
    4. Book Reviews
    1. New Silacycloalkynes with up to Four 1,4-Disila-2-alkyne Units in the Ring (pages 565–566)

      Lektor Dr. Else Kloster-Jensen and Gudveig Aamdal Eliassen

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505651

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      Rings containing two C[TRIPLE BOND]C units flanked on either side by Me2Si units have been obtained by twofold coupling of the reactants 1 (n = 0–4) and 2. Mutual reaction of two ([RIGHTWARDS ARROW] 3) pairs of reactants is preferred, but reactions of three or four pairs are not unknown. When n = 3, 4, traces of seven- and eight-membered cyclo-[Me2Si[BOND](CH2)n[BOND]SiMe2[BOND]C[TRIPLE BOND]C] species, respectively, are also formed.

    2. Light-Induced [2+2] Cycloaddition Reactions of Nonconjugated Dienes—the Effect of Through-Bond Interaction (pages 566–568)

      Prof. Dr. Rolf Gleiter and Dr. Wolfram Sander

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505661

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      The correlation between number of methyl groups and type of product in the reaction outlined below is well known. When n = 1 and 3 formation of 2a is preferred, when n = 2 2b predominates. According to a new hypothesis, electronic factors in educts and transition states are of importance. This is substantiated by orbital and state correlation diagrams.

    3. 15N-29Si Coupling Constants and 15N Isotope Effect on 29Si Chemical Shifts in Compounds with Natural Isotopic Abundance (pages 568–569)

      Dr. Ēriks Kupče, Dr. Edvards Liepiņš and Prof. Dr. Edmunds Lukevics

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505681

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      A new method for determining 1J(15N[BOND]29Si) coupling constants does not use the 29Si satellites in 15N-NMR spectra but the 15N satellites in 29Si-NMR spectra. The sensitivity of this new technique is almost one hundred times that of the technique used earlier. In both cases the INEPT pulse sequence was used. Illustrative examples include, inter alia, the compounds 1 (n = 2–6) and 2 (X = O, S).

    4. Total Synthesis of Ulicyclamide (pages 569–571)

      Prof. Dr. Ulrich Schmidt and Dipl.-Chem. Peter Gleich

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505691

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      A cancerostatic cyclopeptide from a marine organism, which contains both thiazole as well as dihydrooxazole rings, was the first of its kind to be synthesized. A key step in the synthesis is the condensation of the thiazoles 1 and 2 (generated from (S)-isoleucine and (S)-alanine, respectively).

    5. 2,3-Dilithio-1,3-butadienes via Addition of Lithium to Butatrienes (pages 571–572)

      Prof. Dr. Adalbert Maercker and Dipl.-Chem. Ralf Dujardin

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505711

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      The Butatrienes 1 add lithium to the central double bond to give the dilithiobutadienes 2 (over 95% yield). These are not only of theoretical interest but are also suitable as synthetic building blocks (addition of electrophiles). Upon reaction with an excess of lithium in the presence of HgCl2 they undergo cleavage with formation of 1,1-dilithio-1-alkenes 3.

    6. An Organoboron Model System for the Fischer-Tropsch Synthesis (pages 572–573)

      Prof. Dr. Roland Köster and Prof. Dr. Mohamed Yalpani

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505721

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      The reductive C1-polymerization of metal-coordinated CO, e.g. in Fe(CO)5, has been achieved with 9-borabicyclo[3.3.1]nonane (9-H-9-BBN). The compounds 9-alkyl-9-BBN 1 are formed which mainly contain straight chain (but also methyl branched) alkyl residues.

    7. X-Ray Structure Determination of [α-(Phenylsulfonyl)benzyllithium-Tetramethylethylenediamine]2: Chirality of an α-Sulfonyl “Carbanion” (pages 573–575)

      Prof. Dr. Gernot Boche, Michael Marsch, Dr. Klaus Harms and Prof. George M. Sheldrick

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505731

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      The position of the lithium in the title compound 1, which formally contains an α-sulfonyl carbanion, has been clarified by an X-ray structure analysis: In dimeric 1 the two Li atoms are each coordinated to two O atoms and two N atoms. Consistent with this finding, the Cα[BOND]S distance is extraordinarily short.

    8. Solvent Exchange on Magnesium([15]Crown-5) Complexes—a First- and Second-Order Reaction (pages 575–576)

      Prof. Dr. Franz L. Dickert and Dipl.-Chem. Manfred F. Waidhas

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505751

      The mobility of solvate molecules has been investigated NMR spectroscopically on the hydrophobic metal complex 1 in inert solvents. It was possible, for the first time, to observe how the solvent exchange converts from a reaction of second order into one of first order on increasing the concentration. DMF-exchange in 1 is 104 times slower than in [Mg(DMF)6]2+ this can be attributed to an increased interaction between Mg2+ and DMF by the coordination of [15]crown-5. This finding is of interest in connection with the transport of ions by biological membranes.

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    9. 1,5-Diazocines (pages 576–577)

      Dipl.-Chem. Christoph Schnieders, Dr. Walter Huber, Dr. Johann Lex and Prof. Dr. Klaus Müllen

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505761

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      The stable double-bond isomers 1 and 1′ were one of the surprises which the seldom investigated 1,5-diazocines have had to offer. In all other substituted compounds of this class only one isomer with fixed double bonds exists. The dianions are symmetric, diatropic 10π systems with delocalized π bonding; the radical anions are asymmetric with localized charge.

    10. Stepwise Formation of a Dinuclear μ-Aminocarbyne- and a μ-Formimidoyl-Metal Complex by Insertion of Methyl Isocyanide into an MHM Bridge (pages 577–579)

      Ralf Zolk and Prof. Dr. Helmut Werner

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505771

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      Addition of the donor ligand MeNC to the dicobalt complex 1 proceeds with opening of the hydrido bridge. The aminocarbyne complex 2 that is formed rearranges in the presence of methylamine into the μ-N-methylformidoyl complex 3 (anion: PFmath image).

    11. 1,4-Additions of Dihalocarbenes (pages 579–580)

      Prof. Dr. Herbert Mayr and Dipl.-Chem. Ulrich W. Heigl

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505791

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      The unusual 1,4-addition of singlet dihalocarbenes to 1,3-dienes to give 3 occurs, in the case of the cis-fixed 1,3-diene 1, with almost equal justification as the usual 1,2-addition to give 2. The type of generation of the dihalocarbenes CCl2 and CBr2 plays no decisive role regarding the 2:3 ratio.

    12. Octaphenyl-1,5,2λ5,3,4λ5,6λ5,7,8λ5-diazahexaphosphocine (pages 580–581)

      Prof. Dr. Alfred Schmidpeter and Dipl.-Chem. Günther Burget

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505801

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      A cyclotetraphosphazene in which two of the four nitrogen atoms are replaced by phosphorus atoms, i.e. a P6N2 ring, is formed in the reaction of lithium bis(diphenylphosphino)amide 1 with white phosphorus. The salt 2, which is likewise a lithium phosphinoamine, occurs as intermediate; this reacts further with white phosphorus to give the title compound 3, which is stable up to ca. 200°C.

    13. A Macrobicyclic Receptor Molecule for the Diquat Dication (pages 581–584)

      Billy L. Allwood, Franz H. Kohnke, Dr. J. Fraser Stoddart and Dr. David J. Williams

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505811

      A 1:1 complex of [diquat]2+ and a tailor-made derivative of dibenzo[30]crown-10 has been investigated in solution as well as in the solid phase. The crown ether is rigidified by an o-(CH2O)2C6H4 bridge joining the two annelated benzene rings. Complicated exchange reactions in solution were studied NMR spectroscopically. X-ray structure analyses have been carried out on the host molecule and the complex.

    14. Reaction of Thermally Generated (η2-Aryne)zirconocene with W(CO)6, a Novel Route to Carbene Complexes (pages 584–585)

      Priv.-Doz. Dr. Gerhard Erker, Dipl.-Chem. Ulrich Dorf, Dr. Richard Mynott, Dr. Yi-Hung Tsay and Prof. Dr. Carl Krüger

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505841

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      A novel entry to carbene complexes of the Fischer type is provided by reaction of the reactive (η2-aryne)zirconocene 1 with hexacarbonyltungsten to give the intermediate 2, which reacts further in an electrocyclic ring-closure reaction to give 3. The molecule of 3 has an unusual, polymeric, helical chain structure in the crystal.

    15. 1,4-Addition of Dihalocarbenes to 1,3-Dienes (pages 585–586)

      Drs. Leonardus W. Jenneskens, Dr. Willem H. de Wolf and Prof. Dr. Friedrich Bickelhaupt

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505851

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      The direct 1,4-addition of dihalocarbenes to 1,3-dienes is, in contrast to common belief, certainly possible if the diene system such as in 1 is present in the cisoid conformation. Dibromocarbene yields the highest proportion of 1,4-adduct 3; up to 19%!

    16. 2,5,7,10-Tetrakis(trimethylsilyl)-1,6-methano[10]annulene, a Fluxional Valence Tautomer with Cyclopolyolefin Structure (pages 587–588)

      Prof. Dr. Richard Neidlein, Dipl.-Chem. Wolfgang Wirth, Priv.-Doz. Dr. Alfred Gieren, Dr. Viktor Lamm and Dipl.-Chem. Thomas Hübner

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505871

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      Nullification of the aromatic structure of 1,6-methano[10]annulene by substitution is observed in the title compound. In solution at room temperature, single and double bonds fluctuate with concomitant mutual change of conformation of the seven-membered rings, whereas in the crystal a valence structure is frozen in.

    17. Thiophene Derivatives by Novel Rearrangements of Siloxy-substituted Cyclopropanecarboxylates (pages 588–589)

      Dipl.-Chem. Christiane Brückner and Priv.-Doz. Dr. Hans-Ulrich Reissig

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505881

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      The ester enolate of the siloxycyclopropanecarboxylate 1 reacts with CS2 and methyl iodide to give a ring-expanded dihydrothiophene derivative, which, via Lewis acid-induced shifting of an alkyl group, gives the thiophene 2. The reaction can be extended to analogues of 1; the OSi(CH3)3 group, however, is indispensable.

    18. The First Tris(methylene)phosphate Ion (pages 589–590)

      Prof. Dr. Rolf Appel, Elisabeth Gaitzsch and Falk Knoch

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505891

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      A phosphate ion with phosphorus of coordination number three has been obtained for the first time as the lithium salt 2 from the phosphorane 1. According to an X-ray structure analysis the central PC3 group is planar and the CPC angles are almost identical.

    19. syn- and anti-Bishomoperylene (pages 590–592)

      Prof. Dr. Emanuel Vogel, Klaus-Dieter Sturm, Aderson de Farias Dias, Dr. Johann Lex, Dr. Hans Schmickler and Prof. Dr. Fred Wudl

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505901

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      Two 1,6-methano[10]annulene systems are linked together in the title compounds 1(syn) and 2(anti). These novel compounds are of interest as analogues of perylene, which distinguishes itself by the unconventional solid-state properties of some of its derivatives.

    20. 3,8-Methanoaza[10]annulene (Homoisoquinoline) (pages 592–594)

      Dr. Werner Tückmantel, Gertraud Andree, Andreas Seidel, Dr. Hans Schmickler, Dr. Johann Lex, Dr. Elfi Kraka, Michael Haug, Prof. Dr. Dieter Cremer and Prof. Dr. Emanuel Vogel

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505921

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      The second aza-analogue of 1,6-methano[10]annulene, the “homoisoquinoline” 2, has been synthesized in a multistep reaction via 3. Unlike 1, 2 rapidly polymerizes, even in absence of air. According to its spectra and an X-ray structure analysis (of a derivative) 2 is an aromatic compound.

    21. Synthesis of Seven-Membered Rings by [(σ2+π2)+π2] Cycloaddition to Homodienes (pages 594–596)

      Dr. Rainer Herges and Prof. Dr. Ivar Ugi

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505941

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      The cycloaddition of activated vinylcyclopropanes to dienophiles leads to seven-membered rings. This [(σ2+π2)+π2] cycloaddition is presumably the last, still incompletely investigated pericyclic six-center reaction with carbon atoms as reaction centers. Example: Homofuran 1 and homothiophene 2 react with tetracyanoethylene quantitatively in a few minutes at 25°C to give 3 and 4, respectively.

    22. A Triphenylamine Double-Decker (pages 596–597)

      Prof. Dr. Franz A. Neugebauer and Dipl.-Chem. Sigrid Kuhnhäuser

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505961

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      Planar coordinated nitrogen atoms and propeller-like oriented phenyl moieties are present in the “doubled” triphenylamine 1. Compound 1 can serve as a model for studying intramolecular n(σ) electron interactions.

    23. Intramolecular [4+3]-Cycloaddition to 5-Diazomethyl-5H-benzocycloheptenes—a Step in a New Benzosemibullvalene Synthesis (pages 597–599)

      Dipl.-Chem. Manfred Böhshar, Dr. Heinrich Heydt, Priv.-Doz. Dr. Gerhard Maas, Dipl.-Chem. Helmut Gümbel and Prof. Dr. Manfred Regitz

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505971

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      The first [4π+4π]-type [4+3]-cycloaddition ever to be reported takes place intramolecularly in the unsaturated diazo compounds 1. The diazatetracycles 2 thus obtained can be thermolyzed, depending upon the substitutents, to benzosemibullvalenes 3 or dihydrobenzosemibullvalenes.

    24. Highly Active Ylide-Nickel Catalysts for the Polymerization of Ethylene (pages 599–601)

      Dr. K. Alexander Ostoja Starzewski and Dr. Josef Witte

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198505991

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      The nickel complex 1 contains a structurally intact and a carbonyl-stabilized rearranged ylide ligand. Such bis(ylide) complexes are highly active in the polymerization of ethylene; activities of 0.5 × 105 moles of ethylene per mole of 1 are not uncommon.

    25. [(η5-C5Me5)CrO2]2—A Dinuclear Oxo-Complex of Chromium(V) (pages 601–602)

      Prof. Dr. Max Herberhold, Walter Kremnitz, Dr. Abbas Razavi, H. Schöllhorn and Prof. Dr. Ulf Thewalt

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198506011

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      Lower and higher oxidation states of a metal are tolerated by cyclopentadienyl ligands. This is demonstrated by the oxidation of the nitrosyl complex 1 to 2, the first dinuclear oxo complex of chromium(V). The Cr[BOND]Cr and Cr[DOUBLE BOND]O bonds in 2 are remarkably short.

    26. Bis(dihydro-1,2-azaborolyl)tin—a Novel Boron-Nitrogen Stannocene (pages 602–604)

      Prof. Dr. Günter Schmid, Dipl.-Chem. Dagmar Zaika and Dr. Roland Boese

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198506021

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      The sandwich complex 1, which decomposes above −20°C, contains two dihydro-1,2-azaborolyl ligands at an angle of 46.5°. Two diastereomers of 1 can be detected by 1HNMR spectroscopy. 1 forms orange-yellow crystals.

    27. Z-[(η5-C5H5)(CO)2Fe[BOND]P[DOUBLE BOND]C(OSiMe3)(tBu)], a Phosphaalkenyl-Complex with FeP Single Bond (pages 604–605)

      Priv.-Doz. Dr. Lothar Weber, Dipl.-Chem. Klaus Reizig, Dr. Roland Boese and Dipl.-Chem. Michael Polk

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198506041

      The stable monomeric complex 2 is the first phosphaalkene in which a transition metal complex fragment is bound directly to the P atom; 2 was prepared from the ferriophosphane 1 and pivaloyl chloride. The Fe[BOND]P[DOUBLE BOND]C[BOND]O skeleton of 2 is planar; the lone pair on the phosphorus is not required for electronic saturation of the metal.

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    28. Novel Carbonylcyclopropane Dimers and Trimers—Free Ketenes or Organometallic Intermediates? (pages 605–606)

      Dr. Jan-Michael Wulff and Prof. H. M. R. Hoffmann

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198506051

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      The formation of 1,3,5-cyclohexanetriones such as 2 upon reaction of 1 with Zn in MeCN is formally a trimerization of the cyclic ketene (Me3SiCH[BOND]CH2)C[DOUBLE BOND]C[DOUBLE BOND]O. According to model studies, 2 could be formed via an intermediary organometallic compound.

    29. Trispiro[]dodecane-4,8,12-trione (pages 607–608)

      Prof. H. M. R. Hoffmann, Dr. Angela Walenta, Ulrike Eggert and Dr. Dietmar Schomburg

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198506071

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      The highly symmetric trispirotrione 3 could be obtained via the organometallic intermediate 2 by dehalogenating cyclotrimerization of 1-bromocyclopropanecarboxylic chloride 1 with Zn/CuCl in MeCN. According to an X-ray structure analysis the six-membered ring in 3 is drastically flattened.

    30. First 1,4-Dipolar Cycloadditions of 6-Oxo-3,6-dihydro-1-pyrimidinium 4-Olates to Ketenes and Other Carbonyl Compounds (pages 608–609)

      Prof. Dr. Hans Gotthardt and Dipl.-Chem. Karl-Heinz Schenk

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198506081

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      Cycloadditions to the CO[BOND] and not to the C[DOUBLE BOND]C double bond of ketenes are surprisingly observed with pyrimidine betaines. The primary adducts 1 are stable. Results obtained in kinetic measurements are consistent with a synchronous [π4s+π2s] process.

    31. 1,1- and 1,o-Dilithioallyl Phenyl Sulfone: Synthesis, Geminal Cycloalkylation, and Lithium-Titanium Exchange (pages 610–611)

      Dipl.-Ing. Jürgen Vollhardt, Priv.-Doz. Dr. Hans-Joachim Gais and Dr. Karl L. Lukas

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198506101

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      Stepwise lithiation of allyl phenyl sulfone leads via the 1-lithio- to the 1,o-dilithio-derivative 1, which isomerizes to the surprinsingly stable 1,1-dilithio derivative 2. The synthetic potential of 1 and 2 is exceptional. Thus, 2 reacts with (iPrO)2TiCl2 and carbonyl compounds R1R2CO with carbonyl olefination to give 3 and/or with addition to give 4.

    32. Reaction of Homobenzvalene with Tetracyanoethylene; Formation of a Tetracyanodihydrobarbaralane Derivative and a Tetracyanocyclopropane Derivative (pages 611–613)

      Prof. Dr. Manfred Christl, Dr. Reinhard Lang, Dipl.-Chem. Clemens Herzog, Dr. Roland Stangl, Dr. Karl Peters, Eva-Maria Peters and Prof. Dr. Hans Georg von Schnering

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.198506111

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      Benzvalene and homobenzvalene 1 react differently with tetracyanoethylene (TCNE). While benzvalene furnishes only a few percent of the 1,4-cycloadduct, the analogous formation of 2 from 1 is the main reaction; the formation of the cyclopropane derivative 3 from 1 appears to be without example.

  3. Book Reviews

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