A strategy for the preparation of cyclic polyarenes based on single electron transfer-promoted photocyclization reactions |
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Authors: | Hea Jung Park Jung Hei Choi Byeol Na Park Ung Chan Yoon Dae Won Cho Patrick S Mariano |
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Institution: | 1. Department of Chemistry, and Chemistry Institute for Functional Materials, Pusan National University, Busan, 609-735, Korea 2. Department of Chemistry, Yeungnam University, Gyeongsan, Gyeongbuk, 712-749, Korea 3. Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, NM, 87131, USA
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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. |
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