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  • Articles  (4)
  • Organic Chemistry  (4)
  • Iron complexes
  • Phthalocyaninato complexes
  • Wiley-Blackwell  (4)
  • 1970-1974  (4)
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  • Articles  (4)
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  • Wiley-Blackwell  (4)
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  • 1
    Electronic Resource
    Electronic Resource
    Darstellung von Cyclobutanon durch Umlagerung einer Homopropargyl-Verbindung (1971)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 746 (1971), S. 211-213 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Preparation of Cyclobutanone by Rearrangement of a Homopropargyl CompoundSolvolysis of [3-butyne-1-yl]-trifluoromethane sulfonate (1) in trifluoroacetic acid gives cyclobutanone (2; 76%) via a homopropargyl rearrangement.
    Notes: [Butin-(3)-yl-(1)]-trifluormethansulfonat (1) solvolysiert in Trifluoressigsäure unter Homopropargyl-Umlagerung zum Cyclobutanon (2; 76%).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.19717460122
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  • 2
    Electronic Resource
    Electronic Resource
    Umsetzungen von Diazonorcampher mit Säuren (1973)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1973 (1973), S. 1557-1570 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Diazonorcamphor with Acids.Diazonorcamphor (15) reacts with dilute acetic acid in ether partly with rearrangement to give the ketols 4, 5, 6, and 7. The ketols 5 and 7 with an endo OH-group are formed preferentially. In addition to the above compounds, 3-cyclohexene-1-carboxylic acid (1) is also formed, which is explained by fragmentation of the intermediate carbenium ions 19a or 21. Treatment of 15 with hydrogen chloride in ether gives, beside nortricyclanone (14), the isomeric chloronorcamphors 23, 24, and 25 and 2-exo-chlorobicyclo[2.2.1]heptan-7-one (26). Diazonorcamphor (15) also reacts with hydrogen chloride in other solvents, e. g. pentane or liquid sulfur dioxide. Diazonorcamphor (15) reacts with hydrogen fluoride in methylene chloride to give mainly 3-endo-fluoronorcamphor (27) and 2-exo-fluorobicyclo[2.2.1]heptan-7-one (28).
    Notes: Diazonorcampher (15) reagiert mit verdünnter Essigsäure in Äther teilweise unter Umlagerung zu den Ketolen 4, 5, 6 und 7, wobei die Ketole 5 und 7 mit endo-Lage der OH-Gruppe bevorzugt gebildet werden. Daneben entsteht 3-Cyclohexen-1-carbonsäure (1), deren Bildung durch Fragmentierung der intermediären Carbeniumionen 19a oder 21 erklärt wird. Bei der Umsetzung von 15 mit Chlorwasserstoff in Äther werden neben Nortricyclanon (14) die isomeren Chlornorcampher 23, 24 und 25 und das 2-exo-Chlorbicyclo[2.2.1]heptan-7-on (26) gefunden. Diazonorcampher (15) wird auch in anderen Lösungsmitteln, z. B. Pentan oder flüssigem Schwefeldioxid mit Chlorwasserstoff umgesetzt. Mit Fluorwasserstoff in Methylenchlorid reagiert Diazonorcampher (15) überwiegend zum 3-endo-Fluornorcampher (27) und zu 2-exo-Fluorbicyclo[2.2.1]heptan-7-on (28).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197319730917
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  • 3
    Electronic Resource
    Electronic Resource
    Untersuchungen an Cyclopropan-Verbindungen, XV. Solvolyse von cis- und trans-Bicyclo[4.1.0]hept-3-yl-tosylat (1972)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 760 (1972), S. 17-26 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Investigations of Cyclopropane Compounds, XV1). - Solvolysis of cis- and trans-Bicyclo[4,1,0]hept-3-yl-tosylatescis- and trans-Bicyclo[4,1,0]hept-3-yl-tosylate (8b and 9b) solvolyze in an acetone/water mixture without detectable participation by the cyclopropane ring to afford a mixture consisting of cis- and trans-bicyclo[4,1,0]heptan-3-ol (8a and 9a) as well as bicyclo[4,1,0]heptan-2-ol (10). Thus the solvolytic behavior of cis-bicyclo[4,1,0]hept-3-yl-tosylate (8b) contrasts sharply with that of cis-bicyclo[3,1,0]-hex-3-yl-tosylate (6), the first compound for which homocyclopropyl participation was observed.
    Notes: cis- und trans-Bicyclo[4.1.0]hept-3-yl-tosylat (8b bzw. 9b) solvolysieren in Aceton/Wasser-Mischungen ohne merkliche Beteiligung des Cyclopropanringes zu Gemischen aus cis- und trans-Bicyclo[4.1.0]heptan-3-ol (8a bzw. 9a) sowie Bicyclo[4.1.0]heptan-2-ol (10). cis-Bicyclo-[4.1.0]hept-3-yl-tosylat (8b) unterscheidet sich damit charakteristisch vom cis-Bicyclo[3.1.0]-hex-3-yl-tosylat (6), der ersten Verbindung, an der eine Homocyclopropyl-Beteiligung beobachtet wurde.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.19727600103
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  • 4
    Electronic Resource
    Electronic Resource
    Vinylkationen, VIII1) Solvolyse von (α-Brombenzyliden)cyclopropan und 1-Brom-2-phenyl-1-cyclobuten (1973)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1973 (1973), S. 419-431 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Vinyl Cations VIII1).  -  Solvolysis of (α-Bromobenzylidene)cyclopropane and 1-Bromo-2-phenyl-1-cyclobutene(α-Bromobenzylidene)cyclopropane (7) and 1-Bromo-2-phenyl-1-cyclobutene (8) were synthesized and their solvolysis reactions studied in different solvents. Under the conditions used compound 7 reacts preferentially to form cyclopropyl phenyl ketone (15). Compound 8 yields the same ketone 15 by rearrangement. From the solvolysis products and the relatively high reaction rates it is concluded that both bromides react via a vinyl-cation mechanism.
    Notes: (α-Brombenzyliden)cyclopropan (7) und 1-Brom-2-phenyl-1-cyclobuten (8) werden dargestellt und ihre Solvolysereaktionen in verschiedenen Lösungsmitteln untersucht. Verbindung 7 reagiert dabei bevorzugt unter Bildung von Cyclopropylphenylketon (15), aus 8 wird unter Umlagerung ebenfalls das Keton 15 erhalten. Aus den Solvolyseprodukten und den vergleichsweise hohen Solvolysegeschwindigkeiten wird geschlossen, daß beide Bromide über einen Vinylkationenmechanismus solvolysieren.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197319730308
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