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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

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.

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