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  • 1
    Electronic Resource
    Electronic Resource
    1- and 2-fluoroalkyl carboxylates (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 849-853 
    Details
    ISSN: 0947-3440
    Keywords: Organofluorine compounds ; 1-Fluoroalkyl esters ; 2-Fluoroalkyl esters ; Ene esters ; Diene esters ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 2-fluoroalkyl esters (1-4) of carboxylic acids are readily accessible by the base-catalyzed acylation of fluorohydrines. A two-step procedure is required to prepare the 1-fluoroalkyl esters (10-14, 16): conversion of alk-1-enyl carboxylates („ene esters“) into the 2-bromo-1-fluoroalkyl esters 5-9, 15, 17-19 by simultaneous treatment with N-bromosuccinimide and hydrogen fluoride followed by the reductive replacement of bromine by tributyltin hydride. Alka-1,3-dienyl carboxylates („diene esters“) undergo 1,4-addition of bromine and fluorine. The resulting 4-bromo-1-fluoroalk-2-enyl carboxylates 20-25 undergo a substitution reaction with sodium benzenesulfinate to afford the sulfones 26-28 or oxidation with dimethyl sulfoxide to yield the 4-oxo derivatives 29-30.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199505123
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  • 2
    Electronic Resource
    Electronic Resource
    Isopulegol as a Model Compound: Metalation and Substitution of an Allylic Position in the Presence of an Unprotected Hydroxy Function (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 459-462 
    Details
    ISSN: 1434-193X
    Keywords: Electrophilic substitution ; Metalations ; Monoterpene ; Protective groups ; Superbase ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -When treated with butyllithium and potassium tert-butoxide for 2 h at 0 °C in hexanes, the unsaturated monoterpenic alcohol isopulegol is simultaneously deprotonated at the hydroxy function and the allylic methyl group. The metaloxy allylmetal species thus generated can be silylated, alkylated, carboxylated and oxidized to afford the expected products in good to excellent yields. Thus, a specific protection of hydroxy groups is not required, alcohols being instantaneously converted by superbases into alcoholates.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Hydroxy- and Carboxy-Substituted Allylsilanes: A Simple and Stereoselective Method of Preparation (1997)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 130 (1997), S. 335-340 
    Details
    ISSN: 0009-2940
    Keywords: Allylsilanes ; Superbases ; Metalations ; Stereoselectivity ; Cyclizations ; Silicon ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: When treated with two equivalents of a butyllithium/potassium tert-butoxide mixture, terminal olefins carrying unprotected hydroxy or carboxy groups generate allylmetal intermediates which can be trapped with chlorotrimethylsilane to afford functionalized (Z)-2-alkenyltrimethylsilanes. One equivalent of the superbasic reagent suffices if the unsaturated alcohols are first protected as acetals before being subjected to the metalation/silylation/hydrolysis sequence.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19971300306
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