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  • 2020-2022
  • 1965-1969  (11)
  • 1960-1964  (5)
  • 1890-1899
  • Alkenes
  • 1
    Digitale Medien
    Digitale Medien
    The Ene Reaction (1969)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 8 (1969), S. 556-577 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Ene reaction ; Addition ; Alkenes ; C-C coupling ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The ene reaction is defined as the indirect substituting addition of a compound with a double bond (enophile) to an olefin with an allylic hydrogen (ene). For a long time the reaction has been neglected and has remained overshadowed by the related Diels-Alder addition. It is shown that the ene reaction possesses wide scope and applicability ranging from industrial to biosynthetic processes. Preparative aspects are summarized and current views on the mechanism are discussed.
    Zusätzliches Material: 8 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196905561
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  • 2
    Digitale Medien
    Digitale Medien
    Reactions of Electron-Rich Olefins (1968)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 7 (1968), S. 754-765 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Electron-rich alkenes ; Tetraaminoethylen ; Alkenes ; Tetramethoxyethylene ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Olefins are normally preferentially attacked by electrophiles. This trend is strengthened in enol ethers and enamines, and is particularly pronounced in tetramethoxyethylene and in tetraaminoethylenes. These electron-rich olefins are accordingly also excellent reducing agents. In their reactivity, therefore, they behave as counterparts of tetracyanoethylene. This compound shares with the electron-rich olefins a strong tendency to undergo cycloadditions, the electron-rich olefins adding particularly readily to electrophiles.
    Zusätzliches Material: 3 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196807541
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  • 3
    Digitale Medien
    Digitale Medien
    Olefin Alkylation in Biosynthesis (1968)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 7 (1968), S. 903-911 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Alkylation ; Squalene epoxide ; Polyisoprenoid synthesis ; Biosynthesis ; Alkenes ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Stereochemical studies, made possible by asymmetric labeling with hydrogen isotopes, have led to the hypothesis that enzymic association of C5 units in polysoprenoid synthesis is not a concerted process but proceeds in two steps: a trans 1,2-addition to an olefin followed by a trans 1,2-elimination. It is shown that similar mechanisms can also explain the cyclization of squalene epoxide to tetracyclic and pentacyclic triterpenoids.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196809031
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  • 4
    Digitale Medien
    Digitale Medien
    Carbonylation of Olefins under Mild Temperature Conditions in the Presence of Palladium ComplexesDedicated to Professor A. Steinhofer on the occasion of his 60th birthday (1968)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 7 (1968), S. 329-335 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Carbonylation ; Alkenes ; Palladium ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: During a search for catalysts that allow carbonylation reactions on olefins to proceed below 100 °C, complex palladium(II) compounds having the formula LmPdXn were found to be catalytically active. L denotes a ligand such as a phosphine, nitrile, amine, or olefin, X is an acid residue, and m+n is 3 or 4. The catalysts permit the carbonylation of heat-sensitive compounds, as well as selective carbonylation of polyunsaturated olefins. The new process can also be carried out on the industrial scale, as is shown by the carbonylation of cyclododecatriene
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196803291
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  • 5
    Digitale Medien
    Digitale Medien
    The Reduction of Organic Compounds with Chromium(II) Salts (1968)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 7 (1968), S. 247-252 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Reduction ; Chromium ; Alkyl halides ; Alkenes ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Chromium(II) salts can be used for a variety of reductions in organic chemistry; for example, alkyl halides and suitably substituted olefins may both be reduced to alkanes, and alkynes may be converted into trans-olefins. Several epoxyketones are reduced to α,β-unsaturated ketones or β-hydroxyketones, and a nitro steroid was found to give a hydroxy(hydroxyimino) compound. The reduction of alkyl halides is reported to proceed by a free-radical mechanism; the halogen atom that is set free forms a bridge between two chromium atoms.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196802471
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  • 6
    Digitale Medien
    Digitale Medien
    Additions to the Activated CC Triple Bond (1967)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 6 (1967), S. 423-434 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Addition ; Alkenes ; Alkynes ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The possibilities of additions to the activated CC triple bond are discussed with the aid of a number of examples. The additions of donors that contain no active hydrogen are generally initiated via a dipolar primary complex, which can undergo stabilization by rearrangement, cyclization, or addition reactions. Preparative aspects of these reactions are also discussed. They offer routes for the preparation of heterocycles, particularly pyrrole and thiophene derivatives.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196704231
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  • 7
    Digitale Medien
    Digitale Medien
    Allyl-Transition Metal SystemsDedicated to Prof. K. Freudenberg on the occasion of his 80th birthday (1966)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 5 (1966), S. 151-164 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Allyl transition metal systems ; Bis(allyl)nickel ; Nickel ; Polymerization ; Alkenes ; Allylic ligands ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: As a continuation of a report published in 1963, recent results in the field of allyl-transition metal complexes are describedThe term “allyl compounds” in the present paper refers not only to compounds containing the simple allyl group (CH2=CH—CH2—), but also to those that contain substituted allyl groups or allyl groups forming part of a ring system.. Syntheses and reactions of these compounds, as well as the bonding between metal and allyl group, are discussed. Allyl-transition metal complexes form the basis of extremely selective catalysts for homogeneous reactions of 1, 3-diolefins and of olefins; the metal atoms in these “matrix” catalysts are either “bare”The description “bare” is applied to complexed metal atoms from which the ligands can be quantitatively displaced by the substances taking part in catalytic reactions. or are bound to only a few ligands.
    Zusätzliches Material: 3 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196601511
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  • 8
    Digitale Medien
    Digitale Medien
    Eliminations from Olefins (1965)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 4 (1965), S. 49-68 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Elimination ; Alkenes ; Alkynes ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Eliminations from olefins are very often initiated by bases, and usually lead to formation of acetylene derivatives. In view of the numerous side-reactions and subsequent additions or rearrangments observed, the nature of the base used is of considerable significance. Organometallic bases are very versatile. In addition to dehydrohalogenation, dehalogenation by metals, and also thermolytic and photolytic eliminations. (e.g. the retrodiene reaction with exchange of substituents) are discussed. Elimination from low-membered cyclic olefins yields cycloalkynes having strained ring-systems, and the existence of these can be demonstrated by trapping them. The mechanisms known for β-elimination (E2, E1 and E1cB) occur also in the case of olefins; however - due to the sp2-hybridization of the carbon atoms taking part - they are realized with different rates of reaction relative to saturated compounds. α-Eliminations from olefines having aryl residues in the β-position lead to formation of arylacetylenes by rearrangement of the carbon skeleton. The mechanism of this reaction, which is known as the Fritsch-Buttenberg-Wiechell rearrangement, is discussed in considerable detail, and several variations of the reaction are considered. According to present-day knowledge carbenes are involved in α-eliminations only when both β-positions of the olefin are occupied by aliphatic substituents, or when they are occupied by aromatic residues where rearrangement to acetylenes is impossible for steric reasons (as for example with 9-chloromethylenefluorene). With organolithium compounds a number of dehydrohalogenations, which are formally β-eliminations, actually proceed via deprotonation on the halogenbearing carbon atom (α-metallation). α-Metallations are the rate-determining steps when ether is used as solvent, but proceed quickly in tetrahydrofuran even at low temperatures. Compounds of the type \documentclass{article}\usepackage{amssymb}\pagestyle{empty}\begin{document}$\raise1pt\hbox{$〉$}{\rm C}\raise1pt\hbox{=\kern-3.45pt=}{\rm C(Li)Cl}$\end{document} may be prepared by this method and are recognized as intermediates in α-eliminations.
    Zusätzliches Material: 2 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196500491
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  • 9
    Digitale Medien
    Digitale Medien
    New Reactions of Alkylidenephosphoranes and their Preparative Uses. Part II. Alkylidenephosphoranes and Halogen CompoundsFor Part I see Angew. Chem. 77,609 (1965), Angew. Chem. internat. Edit. 4, 583 (1965). Part III will appear shortly in this journal. (1965)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 4 (1965), S. 645-660 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Alkylidenephosphoranes ; Phosphonium salts ; Synthetic methods ; Phosphoranes ; Ylides ; Alkenes ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The reaction of alkylidenephosphoranes with compounds containing halogens can be used to prepare ylides, which can be converted in to useful products, e.g. by hydrolysis, by thermal decomposition, or by other reactions. Examples of such products are ketones including cyclic, unsaturated, and branched-chain ketones (including cyclic, unsaturated, and branched-chain ketones), carboxlic esters (including those of unsaturated, branched- chain, polyenecarboxylic, acetylenecarboxylic, and allenecarboxylic acids), and aldehydes.
    Zusätzliches Material: 10 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196506451
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  • 10
    Digitale Medien
    Digitale Medien
    New Reactions of Alkylidenephosphoranes and their Preparative Uses. Part I: The Acid-Base Character of Phosphonium Salts and AlkylidenephosphoranesParts II and III will appear shortly in this journal. (1965)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 4 (1965), S. 583-587 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Alkylidenephosphoranes ; Phosphonium salts ; Synthetic methods ; Phosphoranes ; Ylides ; Alkenes ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Phosphonium salts may be regarded as Bronsted acids, and alkylidenephosphoranes as the conjugate bases. Compounds of the two classes exist in equilibrium with each other. Phosphonium salts and alkylidenephosphoranes can be obtained by this “transylidation”. Other methods are also given for the preparation of members of both classes.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196505831
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  • 11
    Digitale Medien
    Digitale Medien
    New Reactions of Alkylidenephosphoranes and their Preparative Uses IIIFor Part I, see Angew. Chem. 77, 609 (1965) Angew. Chem. internat. Edit. 4, 583 (1965); for Part II, see Angew. Chem. 77, 651 (1965); Angew. Chem. internat. Edit. 4, 645 (1965).. Alkylidenephosphoranes and Reagents Containing Multiple Bonds (1965)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 4 (1965), S. 830-838 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Alkylidenephosphoranes ; Phosphonium salts ; Synthetic methods ; Phosphoranes ; Ylides ; Alkenes ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: A few examples of preparatively useful syntheses using alkylidenephosphoranes and substances containing a C—N or C—C double bond are the preparations of olefins, allenes, pyran derivatives, and cyclopropane derivatives. Olefins, ketones, and monocyclic compounds can be obtained by autoxidation of alkylidenephosphoranes; α, β-dioxo compounds (including cyclicones) can be prepared by oxidation with peroxy-acids. Alkylidenephosphoranes can also be used for the synthesis of azines and Schiff bases. Of the many possibilities offered by the Wittig reaction, only the preparation of tritiated aldehydes and olefins will be considered.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196508301
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  • 12
    Digitale Medien
    Digitale Medien
    Polar Addition of Hydrogen Halides onto OlefinsThis work was supported by a grant from the National Science Foundation. (1964)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 3 (1964), S. 245-249 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Addition ; Alkenes ; Electrophilic reactions ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Various structures have been proposed for the intermediates of electrophilic additions onto olefins; these include halonium ions, classical carbonium ions, π-complexes (i.e. nonclassical carbonium ions), and π-complexes with back-coordination. It is shown here that it is impossible to use any one of these entities alone to explain all such electrophilic additions; the electrophile itself determines the nature of the transition state formed. Polar addition of hydrogen halides onto olefins appears to proceed via a classical carbonium ion which does not occur as the free ion but as an undissociated ion pair. Various other mechanisms have been excluded by studies reported here of the stereochemical course of such additions.
    Zusätzliches Material: 2 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196402451
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  • 13
    Digitale Medien
    Digitale Medien
    Reactions of Olefins with the Titanium-Carbon BondDedicated to Prof. Dr. Karl Ziegler on the occasion of his 65th birthday (1963)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 2 (1963), S. 704-714 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Titanium ; Alkenes ; Polymerization ; Titanium ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: At low temperatures, ethylene and α-olefins (Δ1-olefins or 1-alkenes) are rapidly converted into oligomrs by the two-component organometallic catalyst CH3TiCl3·CH3AlCl2. To achieve smooth oligomerizations, aromatic or chlorinated hydrocarbons must be used as solvents. Although the activity of the titanium-carbon bond is enhanced by the aluminum component of the catalyst, the aluminum and its methyl group do not participate in the reaction proper; the latter proceeds exclusively at the titanium-carbon bond. The reaction will olefins can be used as an analytical method for the quantitative determination of the titanium-carbon bond in admixture with the organoaluminum component. It is thus possible to follow the reaction leading to formation of the catalyst from titanium tertrachloride, as well as the processes occurring at the titanium-carbon bond during the oligomerization of olefins. All the observations indicate that the catalyst possesses an ionic structure which is determined by the solvent. It is shown that the initial reaction step probably involves formation of a complex between the olefin and the alkyltitanium cation. The reaction scheme proposed is based on organometallic reactions which are characterized by carbanion and hydride transfers within the olefin-cation complex. This mechanism, which is unusual for Ziegler catalysts, is due to the predominance of hydride transfers.
    Zusätzliches Material: 2 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196307041
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  • 14
    Digitale Medien
    Digitale Medien
    Emulsion Polymerization of Vinyl Monomers under the Influence of Ionizing Radiation (1963)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 2 (1963), S. 295-308 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Emulsion polymerization ; Polymerization ; Polymerization ; Alkenes ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Ionizing radiation induces the polymerization of some vinyl monomers in aqueous emulsion with high radiation yields. With identical emulsion compositions, the kinetics of this reaction and the kinetics of emulsion polymerization induced by water-soluble initiators are very similar. The rate of reaction in emulsion polymerization is about one hundred times greater than in bulk polymerization. The initiation of emulsion polymerization by means of ionizing radiation permits uniform “illumination” of the reacting volume, as well as almost any desired variation in the frequency of initiation during the reaction. The sharp decrease in the overall rate of reaction when initiation is interrupted during emulsion polymerization of styrene induced by γ-rays contradicts the earlier concept of sharply separated reaction zones.
    Zusätzliches Material: 11 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196302951
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  • 15
    Digitale Medien
    Digitale Medien
    Type and Extent of Isomerization of Straight-Chain Mono-olefins during the Koch Carboxylic Acid SynthesisReported in part at the meeting of the Gesellschaft Deutscher Chemiker, Aachen 1961; Angew. Chem. 73, 767 (1961). (1963)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 2 (1963), S. 719-722 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Koch carboxylic acid synthesis ; Carboxylic acids ; Alkenes ; Isomerization ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: When straight-chain mono-olefins, from pentene to decene, are subjected to the Koch carboxylic acid synthesis by the addition of CO and H2O or CH3OH in the presence of strongly acidic catalysts, not only the expected secondary acids, but also mixtures of a specific type of tertiary acids or their methyl esters are formed. When the catalysts contain boron trifluoride, the secondary acids are formed in ratios of isomers which are, within the scope of this investigation, independent of the experimental conditions and which agree well with the values calculated from the isomer equilibria of the corresponding n-olefins. Using concentrated sulfuric acid as catalyst, a larger proportion of tertiary acids is obtained than with BF3-catalysis, and amongst the secondary acids, those isomers predominate in which the COOH group is situated near the centre of the molecule.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196307191
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  • 16
    Digitale Medien
    Digitale Medien
    The Oxidation of Olefins with Palladium Chloride Catalysts (1962)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 1 (1962), S. 80-88 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Oxidation ; Palladium ; Catalysis ; Alkenes ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The oxidation of olefins to carbonyl compounds with palladium compounds, especially the oxidation of ethylene to acetaldehyde, is at present carried out on a technical scale. The reaction takes place via a palladium-olefin complex, the formation of which is inhibited by halide ions. Hydrolysis to the carbonyl compound is inhibited by hydrogen ions. The knowledge gained by studying the reaction of olefins with pure solutions of palladium salts allows important conclusions to be drawn concerning the action of technical catalyst solutions containing copper and palladium chloride.
    Zusätzliches Material: 9 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.196200801
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