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  • 1
    Electronic Resource
    Electronic Resource
    Vinylkationen, 36. Solvolyse von Cycloalkylidenmethyl- und 1-Cyclopenten-1-yl-triflaten (1982)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 115 (1982), S. 772-782 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Vinyl Cations, 36. Solvolysis of Cycloalkylidenemethyl and 1-Cyclopenten-1-yl TriflatesCyclohexlidenemethyl triflate (2), cyclobutylidenemethyl triflate (5), 1-cyclopenten-1-yl triflate (7), bicyclo [3.1.0]hex-2-en-2-yl triflate (9), 1-cyclobutylideneethyl triflate (19), and 2-methyl-1-cyclopenten-1-yl triflate (29) were solvolyzed in solvents of various ionizing power and nucleophilicity and the solvolysis products were identified. The cyclobutylidenealkyl triflates solvolyze via a vinyl cation mechanism involving ion pairs with rearrangement to cyclopentene and cyclopentanone compounds. The 1-cyclopenten-1-yl triflates do not produce vinyl cation intermediates but give only the corresponding ketones via an O—S bond cleavage of the triflate group.
    Notes: Cyclohexylidenmethyl-triflat (2), Cyclobutylidenmethyl-triflat (5), 1-Cyclopenten-1-yl-triflat (7), Bicyclo[3.1.0]hex-2-en-2-yl-triflat (9), 1-Cyclobutylidenethyl-triflat (19) und 2-Methyl-1-cyclopenten-1-yl-triflat (29) wurden in Lösungsmitteln verschiedener Ionisierungsstärke und Nucleophilie solvolysiert und die Solvolyseprodukte aufgeklärt. Die Cyclobutylidenalkyl-triflate solvolysieren über Ionenpaarmechanismen (Vinylkationen) unter Umlagerung zu Cyclopenten- und Cyclopentanon-Derivaten. Die 1-Cyclopenten-1-yl-triflate reagieren nicht über Vinylkationen als Zwischenstufe, sondern unter O—S-Spaltung zu den entsprechenden Ketonen.
    Additional Material: 6 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19821150238
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  • 2
    Electronic Resource
    Electronic Resource
    Solvolyse gespannter cyclischer Vinyltrifluormethansulfonate (1978)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1978 (1978), S. 1894-1904 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Solvolysis of Strained Cyclic Vinyl Trifluoromethanesulfonates1-Cyclopentenyl triflate (1-cyclopentenyl trifluoromethanesulfonate, 6), 6,6-dimethylbicyclo[3.1.1]-hept-2-en-2-yl triflate (6,6-dimethyl-2-norpinen-2-yl triflate, 7a) and 1,3-cyclohexadien-2-yl triflate (12) were solvolysed in solvents of various ionizing strength and nucleophilicity. Cyclic vinyl cations were not formed as intermediates in the solvolyse of 6, 7 and 12; product formation occurred via an O-S bond cleavage of the triflate group in nucleophilic solvents.
    Notes: 1-Cyclopentenyltriflat (1-Cyclopentenyltrifluormethansulfonat, 6), 6,6-Dimethylbicyclo[3.1.1]-hept-2-en-2-yltriflat (6,6-Dimethyl-2-norpinen-2-yltriflat, 7a) und 1,3-Cyclohexadien-2-yltriflat (12) wurden in Lösungsmitteln verschiedener Ionisierungsstärke und Nucleophilie solvolysiert. In keinem Fall entsteht dabei ein cyclisches Vinylkation als Zwischenstufe; die Produktbildung erfolgt in nucleophilen Lösungsmitteln durch Spaltung der O-S-Bindung der Triflatgruppe.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197819781203
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