Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Photo-enhanced Reduction of Conjugated Enones with NaBH$_4$

  • Shim, Sang-Chul (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Yeo, Ho-Seop (Department of Chemistry, Korea Advanced Institute of Science and Technology)
  • Published : 1987.06.20
Download PDF
⟨ Previous Next ⟩

Abstract

The reduction of some cyclic conjugated enones with electron-donating substituent on C-3 by sodium borohydride was accelerated on irradiation. The photo-enhanced reduction seems to undergo through zwitterionic species formed from the (n, ${\pi}^{\ast}$) triplet state of conjugated enones, followed by hydride attack to yield unsaturated or saturated alcohols.

Keywords

References

  1. J. Am. Chem. Soc. v.88 G. Balle;P. Cerutti;Witikop
  2. J. Am. Chem. Soc. v.88 P. Yonemitsu;P. cetutti;B. Witikop
  3. Tetrahedron Lett. v.27 J.H. Choi;D.W. Kim;S.C. Shim
  4. J. Am. Chem. Soc. v.90 J.A. Waters;B. Witkop
  5. Tetrahedron Lett. D.C. Wigfield;S. Feiner;F.W. Gowland
  6. J. Am. Chem. Soc. v.95 J.A. Barltrop;D. Bradbury
  7. Utah Dissertation Abstra. v.26 Ph.D. Dissertation Univ. Utah P.W. Jennings
  8. J. Am. Chem. Soc. v.91 P.J. Wagner;D.J. Buchek
  9. J. Am. Chem. Soc. v.89 E.Y. Lam;D. Valentine;G.S. Hammond
  10. J. Am. Chem. Soc. v.89 H.E. Zimmerman;R.W. Binkley;J.J. McCullough;G.A. Zimmerman
  11. J. Org. Chem. v.47 M. Azzaro;J.F. Gal;S. Geribaldi
  12. J. Am. Chem. Soc. v.83 H.C. Brown;K. Ichikawa
  13. Advances in Photochemistry v.5 W.A. Noyes;G.S. Hammond;Pitts
  14. J. Org. Chem. v.29 R.D. Clark;C.H. Heathcock
  15. J. Org. Chem. v.29 W.R. Benson;A.E. Pohland
  16. Syn. Comm. v.5 no.3 E. Piers;Isao Nagakura
  17. Photochemistry J.G. Calvert;J.N. Pitts