Monatshefte für Chemie / Chemical Monthly

, Volume 124, Issue 2, pp 209–215 | Cite as

Direct photolysis and electron transfer photooxygenation of enol acetates of 3-phenylpropiophenones

  • Felipe Algarra
  • María V. Baldoví
  • Hermenegildo García
  • Miguel A. Miranda
  • Jaime Primo
Organische Chemie Und Biochemie

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.

Keywords

Enol acetates of 3-phenylpropiophenones 1,3-Acyl migration Photoinduced electron transfer 2,4,6-Triphenylpyrylium tetrafluoroborate 

Direkte Photolyse und Flektron-Transfer-Photooxygenierung von Enolacetaten von 3-Phenylpropiophenonen

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.

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Copyright information

© Springer-Verlag 1993

Authors and Affiliations

  • Felipe Algarra
    • 1
  • María V. Baldoví
    • 1
  • Hermenegildo García
    • 1
  • Miguel A. Miranda
    • 1
  • Jaime Primo
    • 1
  1. 1.Instituto de Tecnología Química CSIC-UPV y Departamento de QuímicaUniversidad Politécnica de ValenciaValenciaSpain

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