Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Reduction of Selected Carbonyl Compounds with 8-Oxyquinoline Dihydroboronite. Selective Reduction of Aldehydes in the Presence of Ketones

  • Kim, Sung-Gak (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Yang, Sung-Bong (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Kang, Ho-Jung (Department of Chemistry, Korea Advanced Institute of Science and Technology)
  • Published : 1984.12.20
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Abstract

8-Oxyquinoline dihydroboronite is prepared by mixing equimolar amounts of 8-hydroxyquinoline and borane-dimethyl sulfide complex in tetrahydrofuran at room temperature and its structure is determined by spectroscopic methods. The reagent is shown to be an extremely mild reducing agent and reduces aldehydes, cyclohexanones, and acid chlorides to some extent. The reagent in the presence of 0.1 equiv of boron trifluoride etherate in tetrahydrofuran at room temperature reduces selectively aldehydes in the presence of ketones, while the reagent in the presence of 1 equiv of boron trifluoride etherate rapidly reduces simple aldehydes and ketones but does not reduce carboxylic acids, esters, and amides.

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Cited by

  1. ChemInform Abstract: REDUCTION OF SELECTED CARBONYL COMPOUNDS WITH 8-OXYQUINOLINE DIHYDROBORONITE. SELECTIVE REDUCTION OF ALDEHYDES IN THE PRESENCE OF KETONES vol.16, pp.25, 1985, https://doi.org/10.1002/chin.198525116