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Korean Chemical Society (대한화학회)
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Lewis Acid-Catalyzed Reactions of Anthrone: Preference for Cycloaddition Reaction over Conjugate Addition Depending on the Functionality of α,β-Unsaturated Carbonyl Compounds

  • Baik, Woon-Phil (Department of Chemistry, Myoun Ji University) ;
  • Yoon, Cheol-Hoon (Department of Chemistry, Myoun Ji University) ;
  • Koo, Sang-Ho (Department of Chemistry, Myoun Ji University) ;
  • Kim, Ha-Kwon (Department of Chemistry and GNRL, Kyung Hee University) ;
  • Kim, Ji-Han (Department of Chemistry and GNRL, Kyung Hee University) ;
  • Kim, Jeong-Ryul (Department of Chemistry and GNRL, Kyung Hee University) ;
  • Hong, Soo-Dong (Department of Chemistry and GNRL, Kyung Hee University)
  • Published : 2004.04.20
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Abstract

The Lewis acid-catalyzed reactions of anthrone with a variety of ethylenic substrates under various conditions have been studied. It has been observed that depending on kinds of ethylenic substrates and catalysts, products were varied. In particular, the $ZnCl_2$-catalyzed reaction of anthrone with ${\alpha},{\beta}$ -unsaturated ester gave bridged compounds 3 (Diels-Alder adduct type) and mono-Michael adduct 4 exclusively, while the base-catalyzed reaction gave 10,10-bis-Michael adduct as a major product independent of the amount of ethylenic substrate and base. Bridged compounds 3 were easily converted to the corresponding mono-Michael adduct 4 by a catalytic amount of base. Further Michael reaction of mono-Michael adducts with different ethylenic substrates in the presence of a catalytic amount of alkoxide gave unsymmetrical 10,10-bis Michael adducts in good or moderate yields.

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References

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