Research on Chemical Intermediates

, Volume 38, Issue 3–5, pp 847–862 | Cite as

A strategy for the preparation of cyclic polyarenes based on single electron transfer-promoted photocyclization reactions

  • Hea Jung Park
  • Jung Hei Choi
  • Byeol Na Park
  • Ung Chan Yoon
  • Dae Won Cho
  • Patrick S. Mariano


Single electron transfer (SET)-promoted photocyclization reactions of substrates comprised of benzylsilane tethered to phthalimides were subjected to an exploratory study in order to probe a new approach for the preparation of cyclic polyarenes. The results show that UV irradiation of the substrates leads to efficient photochemical reactions that are initiated by SET from benzylsilane moieties to the excited phthalimide acceptor. Ensuing desilylation reactions of the benzylsilane cation radical moieties in the intermediate zwitterionic biradicals and proton transfer gives biradical precursors of the cyclic polyarene products. The observations made in this effort suggests that SET photochemical methods, which have been employed earlier to generate cyclic poly-ethers, -thioethers and -amides, serve as a useful method to access potentially interesting macrocyclic targets.


SET photochemistry Cyclic polyarenes Benzylsilanes Phthalimides 



This investigation was supported financially by the National Research Foundation of Korea Grant to U.C.Y. supported by the Korean Government (KRF-2008-521-C00156). In addition, we offer our congratulation to Professor Kazuhiko Mizuno on the excellent career he has had in the academic profession and for the important scientific contributions he has made to the fields of organic chemistry and organic photochemistry.


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Copyright information

© Springer Science+Business Media B.V. 2011

Authors and Affiliations

  • Hea Jung Park
    • 1
  • Jung Hei Choi
    • 1
  • Byeol Na Park
    • 1
  • Ung Chan Yoon
    • 1
  • Dae Won Cho
    • 2
  • Patrick S. Mariano
    • 3
  1. 1.Department of Chemistry, and Chemistry Institute for Functional MaterialsPusan National UniversityBusanKorea
  2. 2.Department of ChemistryYeungnam UniversityGyeongsan, GyeongbukKorea
  3. 3.Department of Chemistry and Chemical BiologyUniversity of New MexicoAlbuquerqueUSA

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