Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Single Electron Transfer Induced Photoaddition Reactions of Silyl Enol Ether to N-Methylphthalimide

  • Oh, Sun-Wha (Basic Science Research Institute, Pukyong National University) ;
  • Kim, Jin-Young (Department of Chemistry, Pusan National University) ;
  • Cho, Dae-Won (Department of Chemistry, Pusan National University) ;
  • Choi, Jung-Hei (Department of Chemistry, Pusan National University) ;
  • Yoon, Ung-Chan (Department of Chemistry, Pusan National University)
  • Published : 2007.04.20
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Abstract

Photochemical reactions of N-methylphthalimide with silyl enol ethers have been explored. Irradiations of phthalimide (1) and cyclic silyl enol ethers (5a-b) are observed to promote formation of photoreduced phthalimides and photoaddition products by sequential SET-desilylation pathways. The photoreaction of phthalimide (1) and acyclic silyl enol ethers (5c-d) leads to produce oxetanes which arise by competitive single electron transfer (SET) and classical 2+2 photocycloaddition (Parteno-Buchi reaction) pathways.

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References

  1. Yoon, U. C.; Mariano, P. S. Bull. Korean Chem. Soc. 2006, 27, 1099 https://doi.org/10.5012/bkcs.2006.27.8.1099
  2. Ramamurthy, V.; Schanze, K. Organic Photochemistry and Photophysics; Chapter 5. Yoon, U. C.; Mariano, P. S. Mechanistic and Synthetic Aspects of SET-Promoted Photocyclization Reactions of Silicon Substituted Phthalimides; CRC Press: Taylor & Francis, Boca Raton, FL, USA, 2006
  3. Yoon, U. C.; Jin, X. Y.; Oh, S. W.; Park, C. H.; Park, J. H.; Campana, X.; Cai, X.; Duesler, E. N.; Mariano, P. S. J. Am. Chem. Soc. 2003, 125, 10664 https://doi.org/10.1021/ja030297b
  4. Yoon, U. C.; Kwon, H. C.; Hyung, T. G.; Choi, K. H.; Oh, S. W.; Yang, S.; Zhao, Z.; Mariano, P. S. J. Am. Chem. Soc. 2004, 126, 1110 https://doi.org/10.1021/ja0305712
  5. Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 2001, 34, 523 https://doi.org/10.1021/ar010004o
  6. Yoon, U. C.; Oh, S. W.; Lee, C. W. Heterocycles 1995, 41, 2665 https://doi.org/10.3987/COM-95-7029
  7. Mazzocchi, P. H.; Minamikawa, S.; Wilson, P. J. Org. Chem. 1985, 50, 2681 https://doi.org/10.1021/jo00215a017
  8. Mazzocchi, P. H.; Minamikawa, S.; Wilson, P.; Bowen, M.; Narian, N. J. Org. Chem. 1981, 46, 4846 https://doi.org/10.1021/jo00337a005
  9. Mazzocchi, P. H.; Klingler, L.; Minamikawa, S. J. Am. Chem. Soc. 1984, 106, 7567 https://doi.org/10.1021/ja00336a042
  10. Maruyama, K.; Kubo, Y.; Machida, M.; Oda, K.; Kanaoka, Y.; Fukuyama, K. J. Org. Chem. 1978, 43, 2303 https://doi.org/10.1021/jo00405a054
  11. Gassman, P. G.; Bottorff, K. J. J. Org. Chem. 1988, 53, 1097 https://doi.org/10.1021/jo00240a034
  12. Mattes, S. L.; Farid, S. J. Am. Chem. Soc. 1983, 105, 1386 https://doi.org/10.1021/ja00343a061
  13. Pandy, G.; Karthikeyan, M.; Murugen, A. J. Org. Chem. 1998, 63, 2867 https://doi.org/10.1021/jo9718612
  14. House, H. O.; Czuba, L. J.; Gall, M.; Olmstead, H. D. J. Org. Chem. 1969, 34(8), 2324 https://doi.org/10.1021/jo01260a018
  15. Abe, M.; Fujimoto, K.; Nojima, M. J. Am. Chem. Soc. 2000, 122(17), 4005 https://doi.org/10.1021/ja993997i
  16. Yoon, U. C.; Kim, M. J.; Moon, J. J.; Oh, S. W.; Kim, H. J.; Mariano, P. S. Bull. Korean Chem. Soc. 2002, 23(9), 1218 https://doi.org/10.5012/bkcs.2002.23.9.1218

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