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  • Electron transfer reactions  (1)
  • Enol acetates of 3-phenylpropiophenones  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Direct photolysis and electron transfer photooxygenation of enol acetates of 3-phenylpropiophenones (1993)
    Springer
    Monatshefte für Chemie 124 (1993), S. 209-215 
    Details
    ISSN: 1434-4475
    Keywords: Enol acetates of 3-phenylpropiophenones ; 1,3-Acyl migration ; Photoinduced electron transfer ; 2,4,6-Triphenylpyrylium tetrafluoroborate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Die direkte Photolyse von Enolacetaten der 3-Phenylpropiophenone1a–c ergab die zugrundeliegenden Propiophenone2a–c und die 1,3-acyl-verschobenen Produkte3a–c. Im Gegensatz dazu ergab die 2,4,6-Triphenylpyrylium-tetrafluorborat-sensitivierte Photolyse der Substrate1a–c die α-Acetyloxypropiophenone7a–c als generelle Produkte. Diese Ergebnisse sind mit der Erzeugung von Radikalpaaren bei der direkten Photolyse und der Bildung von Radikalkationen beim photoinduzierten Elektronen-Transfer-Prozess zu erklären.
    Notes: Summary Direct photolysis of enol acetates of 3-phenylpropiophenones1a–c gives rise to the parent propiophenones2a–c and the 1,3-acyl shift products3a–c. By contrast, 2,4,6-triphenylpyrylium tetrafluoroborate sensitized photolysis of substrates1a–c affords the α-acetyloxypropiophenones7a–c as the most general products. These results have been rationalized according to the generation of radical pairs in the direct photolysis and radical cations in the photoinduced electron transfer processes.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00808680
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  • 2
    Electronic Resource
    Electronic Resource
    Carbon-Carbon Bond Cleavage of the [2.2]Paracyclophane Radical Cation Generated by Electron Transfer Oxidation with Cerium(IV) Ammonium Nitrate (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 875-879 
    Details
    ISSN: 0009-2940
    Keywords: [2.2]Paracyclophanes ; Electron transfer reactions ; Radicals ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Single electron transfer (SET) oxidation of [2.2]paracyclophane (1) with cerium ammonium nitrate (CAN) produces the corresponding radical cation (1+.), which undergoes cleavage of the carbon-carbon bond of the ethano bridge to generate the double-benzylic radical cation 2+. Trapping of this intermediate by oxygen and nucleophiles gives rise to aldehydes 3, while a second oxidation and subsequent nucleophilic trapping affords nitrates 4. This facile cleavage of the carbon-carbon bond is explained by alignment of the latter with the π systems in the rigid structure of [2.2]paracyclophane, which enables charge delocalization across both benzene rings. When the reaction is carried out in methanol, aromatic substitution takes also place as a minor reaction pathway, which is responsible for the formation of the polyfunctionalized cyclophane 5d.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270514
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    Paper (German National Licenses)
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