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  • Articles  (2)
  • Organic Chemistry  (2)
  • Iron complexes
  • Wiley-Blackwell  (2)
  • 1975-1979  (2)
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  • Articles  (2)
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  • Wiley-Blackwell  (2)
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  • 1
    Electronic Resource
    Electronic Resource
    Umlagerung von 2-Cycloalken-1-onen in 1-Cycloalkenyl(methyl)-ketone (1977)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1977 (1977), S. 614-623 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Rearrangement of 2-Cycloalken-1-ones to 1-Cycloalkenyl Methyl KetonesThe 2-Cycloalken-1-ones 1 and 2 rearrange in various solvents under basic and acidic conditions to form the 1-cycloalkenyl methyl ketones 7 and 8. The mechanism of this new rearrangement reaction is studied in detail using 2-cycloocten-1-one (2) as example. The rearrangement is initiated by a nucleophilic addition of the solvent (e. g. water) to the double bond of the ketone 2. The 3-hydroxycyclooctanone (10) which is formed reacts with retroaldol addition to form 7-oxooctanal (12), from which 1-cyclohexenyl methly ketone (8) is formed via an aldol condensation.
    Notes: Die 2-Cycloalken-1-one 1 und 2 lagern sich in verschiedenen Lösungsmitteln unter basischen und sauren Bedingungen in die 1-Cycloalkenyl(methyl)ketone 7 und 8 um. Der Mechanismus dieser neuen Umlagerungsreaktion wird am 2-Cycloocten-1-on (2) genauer untersucht. Die Isomerisierung wird durch eine nucleophile Addition des Lösungsmittels (z. B. Wasser) an die Doppelbindungs des Ketons 2 eingeleitet. Das dabei entstehende 3-Hydroxycyclooctanon (10) reagiert unter Retroaldolspaltung weiter zu 7-Oxooctanal (12), aus dem durch Aldolkondensation 1-Cyclohexenyl(methyl)keton (8) erhalten wird.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197719770412
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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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