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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 12, Number 6
BKCSDE 12(6)
June 20, 1991 
 
Title
 Selective Reduction by Lithium Bis-or Tris(dialkylamino)aluminum Hydrides. Ⅱ. Reaction of Lithium Tris(dibutylamino)aluminum Hydride with Selected Organic Compounds Containing Representative Functional Groups
Author
 Jin Soon Cha*, Sung Eun Lee, Heung Soo Lee
Keywords
Abstract
 The approximate rates and stoichiometry of the reaction of excess lithium tris(dibutylamino)aluminum hydride (LT-DBA) with selected organic compounds containing representative functional groups under standardized conditions (tetrahydrofuran, O℃) were studied in order to characterize the reducing characteristics of the reagent for selective reductions. The reducing ability of LTDBA was also compared with those of the parent lithium aluminum hydride and the alkoxy derivatives. The reagent appears to be much milder than the parent reagent, but stronger than lithium tri-t-butoxyaluminohydride in reducing strength. LTDBA shows a unique reducing characteristics. Thus, the reagent reduces aldehydes, ketones, esters, acid chlorides, epoxides, and amides readily. In addition to that, α,β-unsaturated aldehyde is reduced to α,β-unsaturated alcohol. Quinones are reduced to the corresponding diols without evolution of hydrogen. Tertiary amides and aromatic nitriles are converted to aldehydes with a limiting amount of LTDBA. Finally, disulfides and sulfoxides are readily reduced to thiols and sulfides, respectively, without hydrogen evolution.
Page
 644 - 649
Full Text
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