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  • 2020-2022
  • 2000-2004  (4)
  • 1960-1964  (5)
  • 1890-1899
  • Alkenes
  • 1
    Digitale Medien
    Digitale Medien
    Mechanism and Extensibility of the Reaction (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 99-104 
    Details
    ISSN: 1434-193X
    Schlagwort(e): Allyl alcohols ; Organocerium reagents ; Alkenes ; Addition reactions ; Cerium ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: ---Alkylcerium reagents add to the multiple bonds of allyl and propargyl alcohols in good yields and under mild conditions. The double bond can be reduced with lithium aluminum hydride in the presence of cerium trichloride. The regiochemistry of the attack depends on electronic factors.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
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  • 2
    Digitale Medien
    Digitale Medien
    Reactions of Pyridine Analogues of Aza-ortho-xylylenes Generated from 1,3-Dialkylpyridosultams (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1263-1270 
    Details
    ISSN: 1434-193X
    Schlagwort(e): Alkenes ; Nitrogen heterocycles ; Pericyclic reactions ; Rearrangements ; Spiro compounds ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -2,3-Dihydro-3-imino-2-methylenepyridines, generated by thermal extrusion of SO2 from 1,3-dialkyl-1,3-dihydroisothiazolo[4,3-b]pyridine 2,2-dioxides (1,3-dialkylpyridosultams), underwent [1,5] hydrogen shifts, which led to 3-alkylamino-2-vinylpyridine derivatives. Cycloalkanespiro-3-pyridosultams 12, which were easily obtained by alkylation of pyridosultams with α,ω-dihaloalkanes, gave, in a similar reaction, 3-alkylamino-2-cycloalkenylpyridine derivatives 14 in good yields. Cyclobutanespiro-3-pyridosultam 12b, after thermal extrusion of SO2, formed cyclobutenyl derivative 14b, which underwent a ring-opening reaction to form butadiene derivative 15. The latter can be trapped with dienophiles, for example, N-phenylmaleimide.
    Materialart: Digitale Medien
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  • 3
    Digitale Medien
    Digitale Medien
    Highly Efficient One-Pot Double-Wittig Approach to Unsymmetrical (1Z,4Z,7Z)-Homoconjugated Trienes (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1821-1826 
    Details
    ISSN: 1434-193X
    Schlagwort(e): Wittig reactions ; Homoconjugated trienes ; Alkenes ; Fatty acids ; Pheromones ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: ---We describe a novel one-pot double-Wittig approach towards unsymmetrically substituted skipped trienes using the symmetrical (Z)-hex-3-ene-1,6-bis(triphenylphosphonium iodide) (2) as key reagent. Double alkenylation of the corresponding bis(ylide) 3 with sequentially added aldehydes gives (Z)-1,4,7-homoconjugated trienes in good yields. Dissymmetrization of the bis(ylide) 3 is feasible, since it displays enhanced reactivity compared to the monoylide resulting from the first olefination. Symmetrical products from statistical coupling of the bis(ylide) 3 can be drastically suppressed by slow release of the first aldehyde component through in situ thermal decomposition of an intermediate aluminate complex, generated by reduction of a methyl ester with DIBAL-H. The novel strategy is successfully applied to the one-pot synthesis of functionalized and isotopically labelled polyunsaturated fatty acids as well as to the synthesis of the geometrid moth pheromone (3Z,6Z,9Z)-nonadeca-1,3,6,9-tetraene (6a). The dissymmetrization strategy was also found to be suitable for the synthesis of homoconjugated dienes from 1,3-propylbis(triphenylphosphonium bromide).
    Zusätzliches Material: 2 Tab.
    Materialart: Digitale Medien
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  • 4
    Digitale Medien
    Digitale Medien
    Hypervalent Iodine-Induced Multi-Component Reactions: Novel Thiocyano- and Isothiocyano-phenylselenenylating Reaction of Alkenes (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1865-1870 
    Details
    ISSN: 1434-193X
    Schlagwort(e): Alkenes ; Iodine ; Selenium ; Sulfur ; Isothiocyanates ; Thiocyanates ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: ---A simple and efficient thiocyano- or isothiocyano-phenylselenenylation of alkenes has been developed. The reactions occur when alkenes are treated with [bis(acetoxy)iodo]benzene, trimethylsilyl isothiocyanate or potassium thiocyanate and diphenyl diselenide. Mono- and disubstituted alkenes led to the formation of 1,2-phenylseleno-thiocyanates, whereas both more-substituted alkenes and styrenes gave exclusively 1,2-phenylseleno-isothiocyanates. The overall transformation represents the addition of PhSeSCN to the olefinic double bonds, in situ generated by the above reagents combination.
    Zusätzliches Material: 2 Tab.
    Materialart: Digitale Medien
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  • 5
    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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  • 6
    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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  • 7
    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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  • 8
    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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  • 9
    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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