Regiochemistry of the Intramolecular [2 + 2]-Photocycloaddition of Cyclohexenone to Vinyl Ethers

Authors

  • Dr. Evelyn Fischer,

    1. Organisch-Chemisches Institut der Universität, Im Neuenheimer Feld 270, D-6900 Heidelberg (FRG)
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  • Prof. Dr. Rolf Gleiter

    Corresponding author
    1. Organisch-Chemisches Institut der Universität, Im Neuenheimer Feld 270, D-6900 Heidelberg (FRG)
    • Organisch-Chemisches Institut der Universität, Im Neuenheimer Feld 270, D-6900 Heidelberg (FRG)
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  • This work was supported by the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie and BASF AG. E. F. thanks the Land Baden Württemberg for a postgraduate grant.

  • Dedicated to Professor Margot Becke-Goehring on the occasion of her 75th birthday

Abstract

original image

What influence have chain length and polarization of the vinyl ether double bond on the title reaction? This problem has been studied with the compounds 1–3. With chains of three and four methylene groups, the different polarization only influences the quantum yield; exclusively head-to-head products are formed. With two methylene groups, the polarization also influences the regiochemistry.

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