Bulletin of the Korean Chemical Society

  • 제14권6호
  • /
  • Pages.743-749
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  • 1993
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Selective Reduction by Lithium Bis- or Tris(dialkylamino)aluminum Hydrides. Ⅶ. Reaction of Lithium Tris(dihexylamino)aluminum Hydride with Selected Organic Compounds Containing Representative Functional Groups$^1$

  • 발행 : 1993.12.20
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초록

The approximate rates and stoichiometry of the reaction of excess lithium tris(dihexylamino)aluminum hydride(LTDHA) with selected organic compounds containing representative functional groups under the standardized conditions (tetrahydrofuran, 0$^{\circ}$C) were studied in order to define the reducing characteristics of the reagent for selective reductions. The reducing ability of LTDHA was also compared with those of the parent lithium aluminum hydride(LAH), lithium tris(diethylamino)aluminum hydride(LTDEA), and lithium tris(dibutylamino)aluminum hydride(LTDBA). In general, the reactivity toward organic functionalities is in order of $LAH{\gg}LTDEA{\geq}LTDBA>LTDHA$. LTDHA shows a unique reducing characteristics. Thus, the reagent reduces aldehydes, ketones, esters, epoxides, and tertiary amides readily. Anthraquinone is cleanly reduced to 9,10-dihydro-9,10-anthracenediol without hydrogen evolution, whereas p-benzoquinone in inert to LTDHA. In addition to that, disulfides are also readily reduced to thiols without hydrogen evolution. However, carboxylic acids, anhydrides, nitriles, and primary amides are reduced slowly. Especially, this reagent reduces aromatic nitriles to the corresponding aldehydes in good yields.

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참고문헌

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피인용 문헌

  1. Reaction of Sodium Cyanoaluminum Hydride with Selected Organic Compounds Containing Representative Functional Groups vol.29, pp.12, 1993, https://doi.org/10.5012/bkcs.2008.29.12.2379
  2. Reaction of lithium tris(tert-butylthiolato)hydridoaluminate with selected organic compounds containing representative functional groups vol.65, pp.1, 2009, https://doi.org/10.1007/s10847-009-9628-4
  3. Thirty Six Years of Research on the Selective Reduction and Hydroboration vol.32, pp.6, 1993, https://doi.org/10.5012/bkcs.2011.32.6.1808