Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Reaction of Potassium 9-sec-Amyl-9-boratabicylco[3.3.1]nonane with Selected Organic Compounds Containing Representative Functional Groups

  • 차진순 (영남대학교 이과대학 화학과) ;
  • 윤말숙 (영남대학교 이과대학 화학과) ;
  • 이광우 (영남대학교 이과대학 화학과) ;
  • 이재철 (영남대학교 이과대학 화학과)
  • Published : 19890200
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Abstract

The approximate rates and stoichiometry of the reaction of excess potassium 9-sec-amyl-9-boratabicylco[3.3.1]nonane (K 9-sec-Am-9-BBNH) with selected organic compounds containing representative functional goups under standardized conditions (tetrahydrofuran, $0^{\circ}C)$ were examined in order to explore the reducing characteristics of the reagent for selective reductions. The reagent readily reduces aldehydes, ketones, acid chlorides and epoxides to the corresponding alcohols. However, carboxylic acid, aliphatic nitriles, t-amides, and some sulfur compounds show very little reactivity or no reactivity to this reagent. The most interesting feature of the reagent is that aromatic nitriles are reduced moderately to the corresponding aldehyde stage, wheras aliphatic nitriles are inert. In addition, the reagent shows a high stereoselectivity toward cyclic ketones at $0^{\circ}C$ and - $25^{\circ}C.$ The selectivity exhibited at $0^{\circ}C$ is comparable to that by lithium trisiamylborohydride at that temperature.

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References

  1. J. Am. Chem. Soc. v.95 C. A. Brown
  2. J. Org. Chem. v.39 C. A. Brown
  3. J. Organomet. Chem. v.156 C. A. Brown;S. Krishnamurthy
  4. Aldrichimica Acta v.7 S. Krishnamurthy
  5. J. Am. Chem. Soc. v.98 S. Krishnamurthy;H. C. Brown
  6. J. Org. Chem. v.41 S. Krishnamurthy;H. C. Brown
  7. Synthesis H. C. Brown;S. C.Kim
  8. Inorg. Chem. v.16 H. C. Brown;A. Khuri;S. C. Kim
  9. J. Am. Chem. Soc. v.100 H. C. Brown;S. Krishnamurthy;J. L. Hubbard
  10. J. Chem. Soc. Chem. Commun. C. A. Brown;S. Krishnamurthy;S. C. Kim
  11. J. Org. Chem. v.49 H. C. Brown;J. S. Cha;B. Nazer;S. C. Kim;S. Krishnamurthy;C. A. Brown
  12. J. Org. Chem. v.49 H. C. Brown;J. S. Cha;B. Nazer
  13. J. Org. Chem. v.50 H. C. Brown;J. S. Cha;B. Nazer;C. A. Brown
  14. J. Org. Chem. v.51 H. C. Brown;W. S. Park;J. S. Cha;B. T. Cho;C. A. Brown
  15. Heterocycles v.27 J. S. Cha;M. S. Yoon;K. W. Lee;J. C. Lee
  16. Tetrahedron Lett. v.29 J. S. Cha;M. S. Yoon;Y. S. Kim;K. W. Lee
  17. Organic Syntheses via Boranes H. C. Brown;G. W. Kramer;M. M. Midland
  18. J. Org. Chem. v.41 H. C. Brown;S. Krishnamurthy;N. M. Yoon
  19. J. Am. Chem. Soc. v.94 H. C. Brown;S. Krishnamurthy

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