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Dienone and Enone Photochemistry(1–3)

  • Dwaine O. Cowan
  • Ronald L. Drisko

Abstract

The photorearrangement of a dienone was noted(4) as early as 1830 in a study of the sesquiterpene α-santonin (1). However, the structure and stereochemistry of the various photoproducts were not conclusively established until 1965.(5) Upon irradiation in neutral media, α-santonin (1) undergoes rapid rearrangement to the cyclopropyl ketone, lumisantonin (2). However, if the irradiation is not terminated after a short period of time the lumisantonin itself rearranges into a linearly conjugated dienone (3). The dienone (3) can be isolated from the photolysis of either (1) or (2) in benzene or ether. In nucleophilic solvents (alcohol or water) the dienone (3) is also photo-chemically active and is further converted into an ester or an acid (photo-santonic acid) (4).

Keywords

Triplet State Bond Order Cyclohexyl Amine Spiro Compound Hydroxy Ketone 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Press, New York 1976

Authors and Affiliations

  • Dwaine O. Cowan
    • 1
  • Ronald L. Drisko
    • 2
  1. 1.The Johns Hopkins UniversityBaltimoreUSA
  2. 2.Essex Community CollegeBaltimoreUSA

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