Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Photochemistry of Conjugated Polyacetylenes. Photoreaction of 1,4-Diphenylbutadiyne with a Mixture of Olefins

  • Chang Beom Chung (Department of Chemistry, korea Advanced Institute of Science and Tehcnology) ;
  • Geon-Soo Kim (Department of Chemistry, korea Advanced Institute of Science and Tehcnology) ;
  • Jang Hyuk Kwon (Department of Chemistry, korea Advanced Institute of Science and Tehcnology) ;
  • Shim Sang Chul (Department of Chemistry, korea Advanced Institute of Science and Tehcnology)
  • Published : 1993.08.20
Download PDF
⟨ Previous Next ⟩

Abstract

Irradiation of 1,4-diphenylbutadiyne (DPB) with a mixture of electron-deficient and electron-rich olefins in deaerated tetrahydrofuran yields a 1 : 1 primary photoadduct between DPB and electron-deficient olefins. Irradiation of the primary photoadduct of DPB and dimethyl fumarate (DMFu) with various olefins such as DMFu, acrylonitrile (AN), and 2,3-dimethyl-2-butene (DMB) in deaerated tetrahydrofuran yields regiospecific 1 : 1 photoadducts. The electron-deficient olefins are more reactive than electron-rich olefins in the photoreaction which proceeds through excited triplet state.

Keywords

References

  1. Angew. Chem. Int. Ed. Engl. v.15 J. H. Lukas;F. Baardman;A. P. Kouwenhoven
  2. J. Org. Chem. v.33 H. M. Rosenberg;P. Serve
  3. J. Org. Chem. v.35 M. P. Serve;H. M. Rosenberg
  4. J. Chem. Soc., Chem. Commun. T. Kubota;K. Shima;H. Sakurai
  5. Tetrahedron Lett. S. Majeti;V. A. Majeti;C. S. Foote
  6. J. Am. Chem. Soc. v.93 D. C. Owsley;J. J. Bloomfield
  7. J. Org. Chem. v.38 T. Kubota;H. Sakurai
  8. Tetrahedron Lett. M. Takahashi
  9. Chem. Lett. S. C. Shim;S. J. Lee;J. H. Kwon
  10. J. Org. Chem. v.55 T. S. Lee;S. J. Lee;S. C. Shim
  11. Tetrahedron Lett. v.31 S. J. Lee;S. C. Shim
  12. Angew. Chem. Int. Ed. Engl. v.22 B. Giese

Cited by

  1. ChemInform Abstract: Photochemistry of Conjugated Polyacetylenes. Photoreaction of 1,4- Diphenylbutadiyne with a Mixture of Olefins. vol.25, pp.13, 1993, https://doi.org/10.1002/chin.199413133
  2. Photoaddition Reactions of Acetylene and Butadiyne Derivatives to Benzodithiophene,1 vol.68, pp.21, 1993, https://doi.org/10.1021/jo034742x