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  • 1
    Electronic Resource
    Electronic Resource
    Mechanism and Extensibility of the Reaction (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 99-104 
    Details
    ISSN: 1434-193X
    Keywords: Allyl alcohols ; Organocerium reagents ; Alkenes ; Addition reactions ; Cerium ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---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.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 2
    Electronic Resource
    Electronic Resource
    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
    Keywords: Alkenes ; Nitrogen heterocycles ; Pericyclic reactions ; Rearrangements ; Spiro compounds ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -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.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 3
    Electronic Resource
    Electronic Resource
    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
    Keywords: Wittig reactions ; Homoconjugated trienes ; Alkenes ; Fatty acids ; Pheromones ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---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).
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 4
    Electronic Resource
    Electronic Resource
    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
    Keywords: Alkenes ; Iodine ; Selenium ; Sulfur ; Isothiocyanates ; Thiocyanates ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---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.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
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