Journal of Photoscience

Korean Society of Photoscience (한국광과학회)
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Photocyclization Reactions of ($\omega$-Phthalimidoalkoxy)acetic Acids via Sequential Single Electron Transfer-Decarboxylation Pathways

  • Yoon, Ung-Chan (Department of Chemistry and the Chemistry Institute for Functional Materials, Pusan National University) ;
  • Lee, Chan-Woo (Department of Chemistry and the Chemistry Institute for Functional Materials, Pusan National University) ;
  • Oh, Sun-Wha (Department of Chemistry and the Chemistry Institute for Functional Materials, Pusan National University) ;
  • Oh, Sun-Wha (Department of Chemistry and the Chemistry Institute for Functional Materials, Pusan National University) ;
  • Hyun Jin kim (Department of Chemistry and the Chemistry Institute for Functional Materials, Pusan National University) ;
  • Lee, Sang-Jin (Department of Chemistry and the Chemistry Institute for Functional Materials, Pusan National University)
  • Published : 2000.12.01
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Abstract

Studies have been conducted to explore single electron transfer(SET) promoted photocyclization of ($\omega$-phthalimidoalkoxy)acetic acids(alkoxy=ethoxy, n-propoxy and n-butyloxy). Photocyclizations occur in methanol or acetone in high yields to produce cyclized products in which phthalimide carbonyl carbon is bonded to the carbon of side chain in place of the carboxylic group. These photocyclizations are thought to proceed through pathways involving intramolecular SET from oxygen in the $\alpha$-carboxymethoxy groups to the singlet excited state phthalimide moieties followed by decarboxylation of the intermediate $\alpha$-carboxymethoxy cation fadicals and cyclizations by radical coupling. The photocyclizations occur ca. three times faster in both methanol or acetone with one equivalent of sodium hydroxide added to the reactions and occur slower in acetone than in methanol. The efficient and regiselective cyclization reactions observed for photolyses in methanol represent synthetically useful processes for construction of heterocyclic compounds.

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References

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