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  • 1
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Trialkylsilyl Trifluoromethanesulfonates, II. - Synthesis of O-Alkyl-O-(trialkylsily1)ketene Acetals and 2-(Trialkylsilyl)carboxylatesAlkyl carboxylates 2 are silylated by trialkylsilyl triflates 1 in the presence of triethylamine (3) to yield ketene acetals 4. In reactions of the esters 6 mixtures of ketene acetals 7 and at the α-carbon silylated esters 8 are obtained. Ethanoic acid esters and lactones are doubly silylated to give the products 11, 12, and 15, respectively. Under suitable conditions silylation of the esters 10 gives rise to the 2-trimethylsilylethanoic acid esters 13. The thermodynamically more stable products are obtained. Product distributions depend on the structure of the esters and the silylating agents 1.
    Notes: Durch Silylierung mit Trialkylsilyltriflaten 1 in Gegenwart von Triethylamin (3) erhält man aus Carbonsäureestern 2 die Ketenacetale 4, die Ester 6 ergeben Gemische aus Ketenacetalen 7 und am α-Kohlenstoffatom silylierten Estern 8. Ethansäureester 10 und Lactone 14 werden durch 1/3 zweifach zu den Produkten 11, 12 bzw. 15 silyliert. Unter geeigneten Bedingungen können 2-(Trimethylsilyl)ethansäureester 13 aus den Estern 10 gewonnen werden. Es resultieren die thermodynamisch stabilen Produkte. Die Abhängigkeit der Produktverteilung von der Struktur der Reaktionspartner wird diskutiert.
    Additional Material: 10 Tab.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 1643-1657 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Trialkylsilyl Trifluoromethanesulfonates, I. - Synthesis of Trialkylsilyl Enol EthersThe reactions of the ketones 2, 2-bromoketones 6, α,β-unsaturated ketones 8, 1,2-diketones, and aliphatic aldehydes 20 with trialkylsilyl triflates 1 in the presence of triethylamine (4) at room temperature yield the silyl enol ethers 3, 7, 9, 11, and 21. The silylation of the unsymmetrical ketones 12 with 1a/4 runs regioselectively in the thermodynamical sense using 1a/12 in excess and yields the enol ethers 13t. The course of this reaction is discussed briefly.
    Notes: Die Ketone 2, 2-Bromketone 6, α,β-ungesättigte Ketone 8, 1,2-Diketone 10 und aliphatische Aldehyde 20 setzen sich mit Trialkyisilyl-triflaten 1 in Gegenwart von Triethylamin (4) bei Raum-temperatur zu den Silylenolethern 3, 7, 9, 11 und 21 um. Die Silylierung unsymmetrischer Ketone 12 mit 1a/4 verläuft mit überschüssigem 1a und 12 regioselektiv im thermodynamischen Sinn zu den Enolethern 13t. Der Reaktionsablauf wird kurz diskutiert.
    Additional Material: 9 Tab.
    Type of Medium: Electronic Resource
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