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

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...

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Bibliographic Details
Published inResearch on chemical intermediates Vol. 38; no. 3-5; pp. 847 - 862
Main Authors Park, Hea Jung, Choi, Jung Hei, Park, Byeol Na, Yoon, Ung Chan, Cho, Dae Won, Mariano, Patrick S.
Format Journal Article
LanguageEnglish
Published Dordrecht Springer Netherlands 01.03.2012
Subjects
Catalysis
Chemistry
Chemistry and Materials Science
Inorganic Chemistry
Physical Chemistry
Cyclic polyarenes
Benzylsilanes
Phthalimides
SET photochemistry
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Summary: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.
ISSN:0922-6168
1568-5675
DOI:10.1007/s11164-011-0422-8