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

A strategy for the preparation of cyclic polyarenes based on single electron transfer-promoted... 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

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

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Publisher
Springer Netherlands
Copyright
Copyright © 2011 by Springer Science+Business Media B.V.
Subject
Chemistry; Catalysis; Inorganic Chemistry; Physical Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-011-0422-8
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Oct 29, 2011

References

  • On the theory of oxidation-reduction reactions involving electron transfer I
    Marcus, RA
  • Kinetics of fluorescence quenching by electron transfer and H-atom transfer
    Rehm, D; Weller, A
  • Five decades of mechanistic and exploratory organic photochemistry
    Zimmerman, HE
  • Applications of phthalimide photochemistry to macrocyclic polyether, polythioether and polyamide synthesis
    Yoon, UC; Oh, SW; Lee, JH; Park, JH; Kang, KT; Mariano, PS
  • Studies aimed at elucidating factors involved in the control of chemoselectivity in single electron transfer promoted photoreactions of branched-polydonor substituted phthalimides
    Cho, DW; Quan, C; Park, HJ; Choi, JH; Kim, SR; Hyung, TG; Yoon, UC; Kim, SH; Jin, YX; Mariano, PS

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