Photoaddition Reactions of 1 , 4 Diphenylbut -1-EN-3-YNE to Quinones

  • Kim, Sung-Sik (Department of Chemistry, Chonbuk National University) ;
  • Kim, Ae-Rhan (Department of Chemistry, Chonbuk National University) ;
  • Chang, Ji-Ae (Department of Chemistry, Chonbuk National University) ;
  • Mah, Yoon-Jung (Department of Chemistry, Chonbuk National University) ;
  • Lim, Jin-Sun (Department of Chemistry, Chonbuk National University) ;
  • Yoo, Dong-Jin (Department of Chemistry, Seonam University) ;
  • Jeon, Il-Cheol (Department of Chemistry, Chonbuk National University)
  • Published : 1999.05.01

Abstract

Irradiation of 1 , 4-diphenylbut-1-en-3-yne 1 and some p-quinones in dichloromethane with 300nm UV light yield tow types of adducts, i.e., p-quinomethanes and cyclobutanes, in which the former were produced via the rearrangement of the intially formed spiro-oxetene intermediates. On the other hadn 1 added to o-quinones to give three types of adducts, i.e., 1, 3-dienes, 1, 4-dioxenes, or spiro-oxetanes, in which the former were found to be applied to synthesize phenanthrene derivatives. A methoxy derivative of enyne 39 was synthesized to investigate the type of thephotoaddition to o-quinones, in which 1, 4-dioxenes were obatained.

Keywords

References

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