Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Selective Reduction of Carbonyl Compounds with Lithium Borohydride, Borane, and Borane-Lithium Chloride (1 : 0.1) in Tetrahydrofuran

수소화붕소리튬, 보란 및 보란-염화리튬 (1 : 0.1)에 의한 카르보닐화합물의 선택환원

  • Nung Min Yoon (Department of Chemistry, College of Science and Engineering, Sogang University) ;
  • Jin Soon Cha (Department of Chemistry, College of Science and Engineering, Sogang University)
  • 윤능민 (서강대학교 이공대학 화학과) ;
  • 차진순 (서강대학교 이공대학 화학과)
  • Published : 1978.08.30
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Abstract

In order to find out the selective reducing characteristics of lithium borohydride, borane, and borane-lithium chloride (1 : 0.1) in the reduction of carbonyl compounds, five representative equimolar mixtures of carbonyl compounds were chosen; benzaldehyde-acetophenone, benzaldehyde-2-heptanone, 2-heptanone-benzophenone, acetophenone-benzophenone, and 2-heptanone-acetophenone, and reacted with limited amount of lithium borohydride, borane or borane-lithium chloride (1 : 0.1) in tetrahydrofuran (THF) at $0^{\circ}$. Borane-lithium chloride (1 : 0.1) showed the excellent selectivity, however, lithium borohydride and borane also exhibited good selectivity except for the 2-heptanone-acetophenone.

수소화붕소리튬, 보란 그리고 보란-염화리튬(1:0.1)의 카르보닐화합물 환원에 있어서의 선택성을 5쌍의 대표적인 카르보닐화합물 쌍(벤즈알데히드-아세토페논, 벤즈알데히드-2-헵탄온, 2-헵탄온-벤조페논, 아세토페논-벤조페논, 2-헵탄온-아세토페논)에 대해서 이들 수소화물의 제한된 양을 반응시켜 알아보았다. 이들 수소화물중 보란-염화리튬(1:0.1)이 제일 선택성이 좋았고, 수소화붕소 리튬과 보란도 2-헵탄온-아세토페논 쌍을 제외하고는 좋은 선택성을 보였다.

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References

  1. 40th Annual Meeting of Korean Chemical Society
  2. J. Amer. Chem. Soc. v.95 R. O. Hutchins;D. Kandasamy
  3. J. Chem. Soc., Chem. Commun. G.W. Gribble;D.C. Ferguson
  4. Aust. J. Chem. v.28 C.S. Sell
  5. J. Org. Chem. v.41 H.C. Brown;S. Krishnamurthy;N.M. Yoon
  6. J. Amer. Chem. Soc. v.98 Y. Yamamoto;H. Toi;A. Sonoda;S.I. Murahashi
  7. J. Org. Chem. v.42 G.H. Posner;A.W. Runquist;M.J. Chapdelaine
  8. Tetrahedron Letters Y. Maki;K. Kikuchi;H. Sugiyama;S. Seto
  9. J. Org. Chem. v.42 H.C. Brown;S.U. Kulkarni
  10. J. Korean Chem. Soc. v.22 N.M. Yoon;J.S. Cha
  11. Tetrahedron v.1 H.C. Brown;O.H. Wheeler;K. Ichikawa
  12. J. Amer. Chem. Soc. v.84 H.C. Brown;K. Ichikawa
  13. J. Korean Chem. Soc. v.21 N.M. Yoon;J.S. Cha
  14. J. Amer. Chem. Soc. v.82 H.C. Brown;Subba Rao
  15. Hydroboration H.C. Brown
  16. Organoboranes in Organic Synthesis J. Klein;G.M.L. Cragg