Angewandte Chemie International Edition in English

Cover image for Vol. 17 Issue 10

October 1978

Volume 17, Issue 10

Pages 701–784

Currently known as: Angewandte Chemie International Edition

  1. Reviews

    1. Top of page
    2. Reviews
    3. Communications
    4. Abstracts
    5. Book Reviews
    1. Extraction with Supercritical Gases—A Foreword (pages 701–702)

      Prof. Dr. Günther Wilke

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807013

      A novel method of separation, extraction with supercritical gases, was the topic of a symposium held at Essen in June of this year. The present issue of Angewandte Chemie International Edition contains all the papers read at this symposium, and thus provides first-hand information about the state of the art. An industrial plant for decaffeination of green coffee beans with supercritical CO2 will shortly be coming on stream.

    2. Separation with Supercritical Gases: Practical Applications (pages 702–709)

      Dr. K. Zosel

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807021

      Extraction of a top residue of petroleum distillation with propane under known conditions gives a dark liquid, while a yellow oil is “destracted” with supercritical propane. The differing phase behavior in the two cases and the principle of fractionation with supercritical gases is illustrated by series of color photographs.

    3. Fluid Extraction of Hops, Spices, and Tobacco with Supercritical Gases (pages 710–715)

      Peter Hubert and Dr. Otto G. Vitzthum

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807101

      The processing of some natural products with carbon dioxide provides an introduction to the engineering principles of extraction with supercritical gases. Physiologically unobjectionable and easy to handle, call unobjectionable and easy to handle, carbon dioxide offers possibilities that are only just starting to be exploited.

    4. Physicochemical Principles of Extraction with Supercritical Gases (pages 716–727)

      Prof. Dr. Gerhard M. Schneider

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807161

      A knowlege of the physicochemical properties of fluid mixtures is of great importance in mastering extraction and chromatography with supercritical gases. Important types of phase diagrams, which are sometimes highly complicated, serve as a basis for disussion, and the occurrence of solid phases is also considered.

    5. Phase Equilibria and Critical Curves of Binary Ammonia–Hydrocarbon Mixtures (pages 728–730)

      Dr. Harro Lentz and Prof. Dr. Ernst Ulrich Franck

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807281

      Liquid or supercritical ammonia is a good solvent for very different classes of compounds. Pertinent information is provied by the phase diagram; measurement of phase data up to high pressures requires special apparatus and methods. Ammonia is a potential mobile phase for extraction and chromatography.

    6. A Quick Method for the Microanalytical Evaluation of the Dissolving Power of Supercritical Gases (pages 731–738)

      Prof. Dr. Egon Stahl, Dipl.-Chem. Winfried Schilz, Dipl.-Chem. Erwin Schütz and Dipl.-Chem. Eberhard Willing

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807311

      The extractability of natural products with supercritical gases can be assessed quickly and elegantly by a new method. The technique employs microextraction with supercritical gases coupled directly with thin layer chromatography as “detector”.

    7. Chromatography with Supercritical Fluids (pages 738–746)

      Priv.-Doz. Dr. E. Klesper

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807381

      Many of the advantages of gas chromatography and liquid chromatography are combined in chromatography with supercritical gases. Separation can be effectvely controlled by pressure programming. The method should be of particular interst for substances of high molecular weight (e.g. styrene oligomer having nominal Mw =2200).

    8. The Separation of Nonvolatile Substances by Means of Compressed Gases in Countercurrent Processes (pages 746–750)

      Prof. Dr. Siegfried Peter and Dr. Gerd Brunner

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807461

      Mixtures of nonvolatile and heat-sensitve substances can be separated by compressed gases in countercurrent columns at lower temperatures than are required for vacuum distillation. The separation of mixtures of oleic glycerides with propane(acetone as entrainer) demonstrates the technical feasibility of the process.

    9. Large-Scale Industrial Plant for Extraction with Supercritical Gases (pages 751–754)

      Dr. R. Eggers

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807511

      Criteria for the design and construction of plant for obtaining carrier material or extracts are discussed for the example of the extraction of natural products with supercritical carbon dioxide.

  2. Communications

    1. Top of page
    2. Reviews
    3. Communications
    4. Abstracts
    5. Book Reviews
    1. Thermal Degradation of Cellulose and Chitin in Supercritical Acetone (pages 754–755)

      Prof. Dr. Peter Köll and Dr. Jürgen Metzger

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807541

      Degradation of natural or man-made polymers in supercritical acetone offers considerable advantages because sensitive products can be detected and secondary reactions largely suppressed. Cellulose and chitin serve as examples to demonstrate the conveint nature of this procedure.

    2. Heterocyclohexaaromatic Compound with Face-to-Face Arrangement of Two Benzene Rings (pages 755–756)

      Prof. Dr. Thomas Kauffmann and Dr. Herbert Lexy

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807551

      Thumbnail image of graphical abstract

      Two benzene rings arranged face are present in the heterocyclohexaaromatic (2). Compound (2) was obtained in good yield via (1) from nonlithiated (1).

    3. [2.2.2.2](1,2,4,5)Cyclophane Quinhydrone—A Donor-Acceptor Cyclophane with an Extremely Short Transannular Distance (pages 756–757)

      Prof. Dr. Heinz A. Staab and Dipl.-Chem. Volker Schwendemann

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807561

      Thumbnail image of graphical abstract

      The new intramolecular quinhydrone(1) exhibits an extremely short distance between the donor and the acceptor: the planes of the bridged ring C atoms are only 2.67 Å apart. Surprisingly, the wavelength and line width of the CT band of (1) are almost the same as those of the pseudogeminal [2.2]paracyclophane quinhydrone.

    4. Indirect Donor-Acceptor Interactions in Quinhydrones of Quadruple-Layered [2.2] Paracyclophanes (pages 757–758)

      Prof. Dr. Heinz A. Staab and Dipl.-Chem. Udo Zapf

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807571

      Thumbnail image of graphical abstract

      Intramolecular charge transfer also takes place in the cyclophane derivatives (1) and (2), in which the donor and acceptor are separated by two π-electron systems. The CT band is unaffected by the mutual spatial orientation of the donor and acceptor units.

    5. A Novel Photochemical Synthesis of Propellanes (pages 758–760)

      Univ.-Doz. Dr. Gerd Kaupp and Dipl.-Chem. Michael Stark

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807581

      Thumbnail image of graphical abstract

      Propellanes can be obtained from excited acyclic chromophores by trapping reactions with bicyclic alkenes. Such a reaction is the one shown below, as is the corresponding reaction of diphenylacetylene.

    6. Simple Template Synthesis of Zinc Tetrabenzporphyrin (page 760)

      Prof. Dr. Arnd Vogler and Dr. Horst Kunkely

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807601

      Thumbnail image of graphical abstract

      Zinc tetrabenzporphyrin (ZnTBP), a model compound for biologically important metalloporphyrins, has long been known but was not readily accessible. This situation has been changed by a new single-step template synthesis.

    7. Acceptor-Substituted Allyl Cations as Ambifunctional Electrophiles (pages 760–762)

      Prof. Dr. Rudolf Gompper and Dipl.-Chem. Rainer Sobotta

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807602

      Thumbnail image of graphical abstract

      Vinamidinium salts like (1) are prototypes of salts of acceptor-substituted allyl cations (A = CO2Et, CO2Me, COPh, etc., R1= H, Me, Ph, CO2Me, etc., R2 =H, Me, Ph, CI, NMe2). These compounds are now readily accessible. In keeping with the charge distribution, they react preferentially at C-3.

    8. 1,3-Bis(dimethylamino)vinylcarbene (pages 762–763)

      Prof. Dr. Rudolf Gompper and Dipl.-Chem. Rainer Sobotta

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807621

      Thumbnail image of graphical abstract

      A nucleophilic vinylcarbene(2) can be obtained from acceptor-substituted vinamidinium salts (1), A = COPh or CO2Et, X=ClO4. (2) can be trapped, e.g. as the zwitterion (3) with tetraethyl allenetetracarboxylate.

    9. Synthesis of Penta- and Hexacyclic Conjugated Hydrocarbons by Cycloaddition Reactions (pages 763–764)

      Prof. Dr. Klaus Hafner, Dr. Hans Dieter Diesel and Dr. Winfried Richarz

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807631

      Thumbnail image of graphical abstract

      New conjugated hydrocarbons with five or six annelated rings have been obtained by cycloaddition. The reaction of (1) with (2) is an example.

    10. 2,3-Dioxa-7-thiabicyclo[2.2.1]heptane: A New Heterobicyclic System Possessing the Thiaozonide Structure (page 765)

      Prof. Dr. Waldemar Adam and Henny J. Eggelte

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807651

      Thumbnail image of graphical abstract

      The first thiaozonides of type(1) have now been synthesized and characterized. (1a), R = Me, and (1b), R = tBu, are stable at −20°C but decompose to diketones at room temperature.

    11. Synthesis and Stereochemical Consequences of Protonation of a Bishomodihydrotetraaza[14]annulene: A New Macrocyclic Complex Ligand (pages 765–767)

      Prof. Dr. Helmut Quast, Dr. Josef Stawitz, Dr. Karl Peters and Prof. Dr. Hans Georg von Schnering

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807652

      Thumbnail image of graphical abstract

      Far-reaching structural changes occur on protonation of the tetraaza[14] annulene derivative (2): the cyclic dication is shown by X-ray analysis to posses two separate “open” 6π systems with extensively delocalized charge. (2) forms complexes with metal ions, e.g. with Ni2+.

    12. Decamethyl-1λ3,4λ3-diphospha-2,3,5,6,7-pentastannabicyclo[2.2.1] heptane, a Bicyclic Compound Rich in Tin (pages 767–768)

      Dr. Bernd Mathiasch and Dr. Martin Dräger

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807671

      Thumbnail image of graphical abstract

      A “norbornane” whose skeleton contains five tin and two phosphorus atoms is formed on base-catalyzed reaction of dimethylstannane with white phosphorus (DMF/Et2O/295K). The rigid bicyclic skeleton is retained in solution.

    13. (Z)-5-Decenyl Acetate, a Sex Attractant for the Male Turnip Moth Agrotis segetum (Lepidoptera) (page 768)

      Prof. Dr. Hans Jürgen Bestmann, Dr. Otto Vostrowsky, Dipl.-Chem. Karl-Heinz Koschatzky, Dipl.-Chem. Hans Platz, Dipl.-Chem. Thorolf Brosche, Dr. Iwan Kantardjiew, Marlies Rheinwald and Dr. Werner Knauf

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807681

      Thumbnail image of graphical abstract

      The world-wide agricultural pest Agrotis segetum still proves difficult to eradicate. (Z)-5-Decenyl acetate (1) has now been identified as sex attractant for the male. Trials can thus start on biological methods of combatting this pest.

    14. Enantioselective Synthesis of Homoallyl Alcohols via Chiral Allylboronic Esters (pages 768–769)

      Dipl.-Chem. Thomas Herold and Prof. Dr. Reinhard W. Hoffmann

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807682

      Thumbnail image of graphical abstract

      Optically active homoallyl alcohols of type (2) are preparable in good yields by an enantioselective synthesis. endo-Phenyl-exo,exo -glycol, which affords the ester (1) with boranes B(CH2[BOND]CR2[DOUBLE BOND]CH2)3, serves as (regenerable) chiral auxiliary compound.

    15. Functional Derivatives of D- and L-Ribose by Optical Resolution with Recycling (pages 769–770)

      Prof. Dr. Richard R. Schmidt and Dipl.-Chem. Albrecht Lieberknecht

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807691

      Thumbnail image of graphical abstract

      A concept for chiral synthesis of functionalized carbohydrates is based on the reversible alcoholysis of the meso-anhydrite (1) with isopropanol. The enantiomeric products D-(2) and L-(2), X = OH, can be separated with brucin and subsequently subjected to further transformation. The undesired isomer of (2) is reconverted into (1) by means of Ac2 O.

    16. Synthesis of the Tetrasaccharide Chains of the Determinants of Blood Group Substances A and B (page 771)

      Prof. Dr. Hans Paulsen and Dipl.-Chem. Čeněk Kolář

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807711

      Thumbnail image of graphical abstract

      The terminal carbohydrate chain of the blood group substances of the AB0 system represents the determinant structure of the antigene responsible for the pronounced immunological specificity of these glycoproteins. The tetrasaccharide chain of substances A and B have now been synthesized.

    17. Direct Synthesis of Metal-Free 1,8-Dihydrotetraaza-[14]annulenes Utilizing the Metal-Template Effect (page 772)

      Dipl.-Chem. Gerhold Mühmel and Prof. Dr. Eberhard Breitmaier

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807721

      Thumbnail image of graphical abstract

      A variant of the metal template synthesis leads to metal-free ligands if the ionic radius of Mn+ is significantly lower (e.g. Mg2+) or higher than 70 pm (e.g. Mn2+). Yields in the presence of Mn+ can far exceed those obtained in the absence of Mn+. Compound (1) is obtained from enediamine and MX.

    18. Synthesis of 5′-O-Glycosyl-ribo-nucleosides (pages 772–774)

      Prof. Dr. Frieder W. Lichtenthaler, Dr. Yuzuru Sanemitsu and Dr. Toshihiro Nohara

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807722

      Thumbnail image of graphical abstract

      A group of novel bacterial metabolites, nucleosides of type (1), can vary in the base, the hexose moiety, and the intersaccharide bond. Some representatives, such as (1), R = H, X = adenyl, have now been synthesized.

    19. Synthesis of a Δ4-1,4,2λ5-Selenazaphospholine, the First Selenophosphorane (pages 774–775)

      Priv.-Doz. Dr. Klaus Burger, Dr. Ralph Ottlinger, Dr. Albin Frank and Dr. Ulrich Schubert

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807741

      Thumbnail image of graphical abstract

      A phosphorus atom with three oxygen, one carbon, and one selenium ligand is to be found in the spiro compound (3). This species is the first representative of the selenophosphoranes proposed on several occasions as intermediates.

    20. Scope of Application of the Isoselective Relationship (pages 775–777)

      Prof. Dr. Otto Exner and Prof. Dr. Bernd Giese

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807751

      Comparison of activation parameters requires a statistically correct treatment in order to prove the validity of the isoselective relationship in specific cases, and to calculate the isoselective temperature for pairs of series of reactions.

    21. Synthesis of Carbocyclic Carbene Complexes by Metal-Induced Diazocyclopentadiene Fragmentation (pages 777–778)

      Priv.-Doz. Dr. Wolfgang A. Herrmann, Johann Plank, Prof. Dr. Manfred L. Ziegler and Dipl.-Chem. Klaus Weidenhammer

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807771

      Thumbnail image of graphical abstract

      The first metal complex to contain an oligocyclic dicarbene is formed as a result of a hitherto unobserved [2+2] cycloaddition of the carbene liberated from (1). The structure of (2) is confirmed by X-ray structure analysis.

    22. A Cyclotetra(azadithiane)—The First Twelve-Membered Sulfur-Nitrogen Ring (page 778)

      Prof. Dr. Bernt Krebs, Dipl.-Chem. Michael Hein, Dipl.-Chem. Manfred Diehl and Prof. Dr. Herbert W. Roesky

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807781

      Thumbnail image of graphical abstract

      A ring made up of eight sulfur and four nitrogen atoms is present in S8N4(SO2CF3)4; this is the largest sulfur-nitrogen ring yet prepared. Its synthesis was at least facilitated, if not made possible, by the electron-withdrawing trifluoro-methanesulfonyl substituent.

    23. A New Cationic Mono-Hydride-Bridged Binuclear Platinum (II) Dihydride (pages 778–779)

      Gustav Bracher, Dr. David M. Grove, Prof. Luigi M. Venanzi, Dr. Fiorella Bachechi, Dr. Pasquale Mura and Prof. Luigi Zambonelli

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807782

      Thumbnail image of graphical abstract

      A nonlinear Pt[BOND]H[BOND]Pt group is the characteristic feature of the cation (1), which is surprisingly formed from trans-[PtH(NO3)(Et3P)2] and Na[BPh4]. In contrast to other binuclear platinum hydrates, (1) does not contain a (stabilizing) bidentate donor ligand.

    24. Trimethylphosphoranediyl- and -arsoranediylmethyl-(trimethylsiloxy)carbene Complexes by 1,3-Silyl Shift (page 780)

      Priv.-Doz. Dr. Wolfgang Malisch, Dipl.-Chem. Herbert Blau and Siegfried Voran

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807801

      Thumbnail image of graphical abstract

      Direct transformation of complexed CO into an ylide carbene ligand is accomplished by addition of silyl ylides such as (1) to M(CO)6, M = Cr, Mo, W, and subsequent 1,3-silyl shift. The first (arsenic ylide) carbenemetal complex (2), M = Mo, As in place of P, was obtained in a similar manner

    25. Dichlorocarbene Complexes of Iron(II)-Porphyrins–Crystal and Molecular Structure of Fe(TPP)(CCl2)(H2O) (pages 781–782)

      Dr. Daniel Mansuy, Dr. Marc Lange, Prof. Dr. J. C. Chottard, Dr. J. F. Bartoli, Dr. Bernard Chevrier and Prof. Dr. Raymond Weiss

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807811

      Thumbnail image of graphical abstract

      The structure of an iron porphyrin with dichlorocarbene as ligand has now been estabished by X-ray analysis. The complex (1) accordingly contains a planar Fe(TPP)skeleton with H2O and CCl2 as axial ligands. The structural unit (2) is almost linear.

  3. Abstracts

    1. Top of page
    2. Reviews
    3. Communications
    4. Abstracts
    5. Book Reviews
    1. ABSTRACTS (pages 782–783)

      Version of Record online: 22 DEC 2003 | DOI: 10.1002/anie.197807821

  4. Book Reviews

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

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