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Regio- and endo-selective

Kokubo1, Nakajima, Iijima

  • 1Department of Applied Chemistry, Faculty of Engineering, Osaka University, Toyonaka, Osaka 560-0043, Japan.

The Journal of Organic Chemistry
|June 8, 2000
PubMed
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Photochemical [2 + 2] cycloaddition of homobenzoquinones with ethyl vinyl ether yields tricyclic diones. Substituent effects dictate regioselectivity and stereochemistry, with some adducts undergoing skeletal rearrangement.

Area of Science:

  • Organic Photochemistry
  • Synthetic Organic Chemistry
  • Cycloaddition Reactions

Background:

  • Homobenzoquinones are versatile substrates in photochemical reactions.
  • Ethyl vinyl ether is a common dienophile in cycloadditions.
  • Understanding substituent effects is crucial for predicting reaction outcomes.

Purpose of the Study:

  • To investigate the [2 + 2] photoaddition of substituted homobenzoquinones with ethyl vinyl ether.
  • To determine the regioselectivity and stereoselectivity of the cycloaddition.
  • To explore potential subsequent reactions of the photoadducts.

Main Methods:

  • Photochemical irradiation of homobenzoquinones and ethyl vinyl ether.
  • Analysis of reaction products using spectroscopic techniques.

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  • Investigation of substituent effects on reaction pathways.

    • Main Results:

    • Regio- and endo-selective formation of tricyclic diones via [2 + 2] photoadducts.
    • Predominant head-to-head addition observed for various substituents (CH(3), Cl, Br, CH(3)O).
    • Bromine-substituted adducts underwent skeletal rearrangement to form new derivatives.

    Conclusions:

    • The [2 + 2] photocycloaddition provides an efficient route to complex tricyclic diones.
    • Substituent identity significantly influences the stereochemical outcome and subsequent reactivity.
    • The observed skeletal rearrangement offers a pathway to novel dihydrobenzofuran and dihydro-o-benzoquinone derivatives.