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  • Organic Chemistry  (2)
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  • 1
    Electronic Resource
    Electronic Resource
    2,3-Donor-Acceptor-Substituted 1,3-Butadienes. Synthesis by SO2-extrusion from 3-sulfolenes and diels-alder reactions (1994)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 336 (1994), S. 343-349 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The thermal extrusion of SO2 from disubstituted 3-sulfolenes 3 leads to 2,3-donor-acceptor-substituted 1,3-butadienes 4. These dienes react with acrylic acid ester and ethyl vinyl ether to the corresponding Diels-Alder adducts 5 and 6 and with themselves to the cyclic dimerization products 7 and 8. The regiochemistry of the cycloadducts has been determined by chemical- and NMR-methods.The pyrolysis of 3-sulfolene 11 afforded the thiolactone 13 whose structure has been verified by X-ray diffraction analysis. In addition, the influence of Lewis acid catalysts on the Diels-Alder reaction and an approach to transition state calculation by means of the semiempirical AM 1 method has also been investigated.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19943360413
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  • 2
    Electronic Resource
    Electronic Resource
    Cycloadditions, 53. New spirocyclic chiral dienes  -  synthesis and diastereoselective Diels-Alder reactions with N-phenylmaleimide (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1455-1461 
    Details
    ISSN: 0947-3440
    Keywords: Dienes, chiral ; 1,3-Dioxin-4-ones ; (-)-Menthone ; Diels-Alder reactions, diastereoselective ; Cycloadditions, high-pressure ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis and diastereoselective Diels-Alder reactions of new spirocyclic chiral dienes are reported. Starting with diketene and (-)-menthone (1), we prepared the diastereomeric diketene-menthone adducts 2 and 3. Further derivatization and olefination afforded four chiral dienes 12-15. Diastereoselective Diels-Alder reactions of these dienes with N-phenylmaleimide (NPM) under high-pressure conditions yielded the corresponding cycloadducts 16-19. Olefination of 6-diethylphosphonomethyl-2,2-dimethyl-1,3-dioxin-4-one 8 with formaldehyde led to unexpected compounds 9-11 resulting from the originally formed olefination product.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199508198
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