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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
    Prescriptions and Ingredients for Controlled CC Bond Formation with Organometallic Reagents. New synthetic methods (5) (1974)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 13 (1974), S. 701-706 
    Details
    ISSN: 0570-0833
    Keywords: Organometallic compounds ; C-C coupling ; Copper ; Potassium ; Synthetic methods ; Sodium ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Merits and drawbacks of known carbon-carbon linking procedures are outlined. Two novel methods are discussed in some detail: the copper-catalyzed alkylation of Grignard reagents and reactions with allylpotassium compounds. Both methods provide a very efficient access to saturated, unsaturated, as well as functionally substituted hydrocarbons and moreover permit an astonishing degree of regio- and stereoselective control of olefin synthesis.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.197407011
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