Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Studies of Silyl-Transfer Photochemical Reactions of N-[(Trimethylsilyl)alkyl]saccharins

  • Cho, Dae-Won (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Oh, Sun-Wha (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Kim, Dong-Uk (Department of Science Education, Daegu National University of Education) ;
  • Park, Hea-Jung (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Xue, Jin-Ying (College of Chemistry and Chemical Engineering, Harbin Normal University) ;
  • Yoon, Ung-Chan (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Mariano, Patrick S. (Department of Chemistry and Chemical Biology, University of New Mexico)
  • Received : 2010.06.14
  • Accepted : 2010.07.01
  • Published : 2010.09.20
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Abstract

Photochemical studies of N-[(trimethylsilyl)alkyl]saccharins were carried out to investigate their photochemical behavior. Depending on the nature of the substrate and the solvent system employed, reactions of these substances can take place by either SET-promoted silyl migration from carbon to either the amide carbonyl or sulfonyl oxygen or by a N-S homolysis route. The results of the current studies show that an azomethine ylide, arising from a SET-promoted silyl migration pathway, is generated in photoreactions of N-[(trimethylsilyl)methyl]saccharin and this intermediate reacts to give various photoproducts depending on the conditions employed. In addition, irradiation of N-[(trimethylsily)ethyl]saccharin produces an excited state that reacts through two pathways, the relative importance is governed by solvent polarity and protic nature. Finally, photoirradiation of N-[(trimethylsilyl)propyl]saccharin in a highly polar solvent system comprised of 35% aqueous MeOH gives rise to formation of a tricyclic pyrrolizidine and saccharin that generated via competitive SET-promoted silyl transfer and $\gamma$-hydrogen abstraction pathways.

Keywords

References

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