Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Lithium Aluminum Hydride Reduction Studies of Rigid $\alpha$-Oximino Ketones

  • Kim, Jack C. (Department of Chemistry, College of Natural Sciences and The Institute for Solid State Physics Busan National University) ;
  • Lee, Young-Tae (Department of Chemistry, College of Natural Sciences and The Institute for Solid State Physics Busan National University) ;
  • Kim, Min-Sook (Department of Chemistry, College of Natural Sciences and The Institute for Solid State Physics Busan National University) ;
  • Woo, Young-Min (Department of Chemistry, College of Natural Sciences and The Institute for Solid State Physics Busan National University) ;
  • Shin, Hong-Dae (Department of Chemistry, College of Natural Sciences and The Institute for Solid State Physics Busan National University) ;
  • Cho, In-Seop (Department of Chemistry, College of Natural Sciences and The Institute for Solid State Physics Busan National University)
  • Published : 1982.09.30
Download PDF
⟨ Previous Next ⟩

Abstract

Rigid ${\alpha}$-oximino ketones containing two functional groups such as 2-oximino-1-acenaphthenone and 2-oximino-1-indanone were synthesized and the simultaneous reduction of the two functional groups of ${\alpha}$-oximino ketones by $LiAlH_4$ gave the corresponding amino alcohols, 2-amino-1-acenaphthenol and 2-amino-1-indanol. The yields of the reduction products of the ${\alpha}$ -oximino ketones remarkably increased, as the increase of molar ratio of hydride used to the reactant. The use of 24 moles of $LiAlH_4$ was found to afford the best result in the reduction of the rigid ${\alpha}$-oximino ketones to the corresponding amino alcohols. The yields was not affected by the variation of solvents such as ether, THF and diglyme.

Keywords

References

  1. Modern Synthetic Reactions H. O. House
  2. J. Amer. Chem. Soc. v.70 R. F. Nystron;W. C. Brown
  3. J. Amer. Chem. Soc. v.74 A. Burger;E. D. Hornbaker
  4. J. Amer. Chem. Soc. v.73 J. H. Blyer
  5. J. Org. Chem. v.16 K. Kayes;G. Gever
  6. J. Chem. Soc. G. L. Gergory;T. Malkin
  7. J. Amer. Chem. Soc. v.80 M. P. Cava;R. L. Little;D. B. Napier
  8. J. Org. Chem. v.17 D. R. Smith;M. Maienthal;J. Tipton
  9. Modern Synthetic Reactions H. O. House
  10. J. Amer. Chem. Soc. v.90 N. M. Yoon;H. C. Brown
  11. J. Amer. Chem. Soc. v.88 H. C. Brown;P. M. Weissman;N. M. Yoon
  12. Tetrahedron Lett. M. H. A. Kada
  13. J. Amer. Chem. Soc. v.87 H. C. Brown;C. J. Shoaf
  14. J. Amer. Chem. Soc. v.87 P. T. Lansbury;R. E. Mcleay
  15. Tetrahedron Lett. P. S. Portoghese;D. A. williams