Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
권호 표지

Selective Reduction with Zinc Borohydride. Reaction of Zinc Borohydride with Selected Organic Compounds Containing Representative Functional Groups

수소화붕소아연에 의한 선택환원. 수소화붕소아연의 대표적 유기화합물과의 반응

  • Yoon Nung Min (Department of Chemistry, College of Science and Engineering, Sogang University) ;
  • Ho Jun Lee (Department of Chemistry, College of Science and Engineering, Sogang University) ;
  • Hye Kyu Kim (Department of Chemistry, College of Science and Engineering, Sogang University) ;
  • Jahyo Kang (Department of Chemistry, College of Science and Engineering, Sogang University)
  • 윤능민 (서강대학교 이공대학 화학과) ;
  • 이호준 (서강대학교 이공대학 화학과) ;
  • 김혜규 (서강대학교 이공대학 화학과) ;
  • 강재효 (서강대학교 이공대학 화학과)
  • Published : 1976.02.29
Download PDF
⟨ Previous Next ⟩

Abstract

The addition of one mole of zinc chloride to 2.33 moles of sodium borohydride in tetrahydrofuran at room temperature gave a clear chloride-free supernatant solution of zinc borohydride after stirring three days and standing at room temperature.The approximate rates and stoichiometry of the reaction of zinc borohydride with 54 selected organic compounds were determined in order to test the utility of the reagent as a selective reducing agent. Aldehydes and ketones were reduced rapidly, aromatic ketones being somewhat slowly, and the double bond of cinnamaldehyde was not attacked. Acyl halides were reduced rapidly within one hour, but acid anhydrides were reduced at a moderate rate. Carboxylic acids, both aliphatic and aromatic, were slowly reduced to alcoholic stage. Esters were inert to this reagent but a cyclic ester, γ-butyrolactone, was slowly attacked. Primary amides were reduced slowly with partial evolution of hydrogen, whereas tertiary amides underwent neither reduction nor hydrogen evolution. Epoxides and nitriles were all inert, as well as nitro, azo, and azoxy compounds. Cyclohexanone oxime and phenyl isocyanate were reduced slowly but pyridine was inert. Disulfide, sulfoxide, sulfone and sulfonic acids were stable to this reagent.

수소화붕소아연의 선택환원성을 조사하기 위하여 대표적 유기화합물 54종을 택하여 수소화붕소 아연과 일정한 조건 (THF 용액, 실온, 수소화이온의 농도 : 0.5M, 유기화합물의 농도 : 0.125M)하에서 반응시켜 대략의 반응속도와 정량관계를 알아보았다.

Keywords

References

  1. Reduction with Complex Metal Hydride N. G. Gaylord
  2. Boranes in Organic Chemistry H. C. Brown
  3. Reduction R. L. Augustine
  4. J. Amer. Chem. Soc. v.92 H. C. Brown;P. Heim;N.M. Yoon
  5. J. Amer. Chem. Soc. v.92 H. C. Brown;D. B. Bigley;S. K. Arora;N. M. Yoon
  6. J. Org. Chem. v.37 H. C. Brown;P. Heim;N. M. Yoon
  7. J. Amer. Chem. Soc. v.88 H. C. Brown;N. M. Yoon
  8. J. Amer. Chem. Soc. v.73 H. I. Schlesinger (et al.)
  9. Z. Naturforsch. v.76 E. Wtberg;W. Henle
  10. Z. Anorg. Allg. Chem. v.370 H. Noth;E. Wiberg;L. P. Winter
  11. J. Amer. Chem. Soc. v.82 W. J. Gensler;F. Johnson;D. B. Sloan
  12. J. Amer. Chem. Soc. v.85 W. J. Gensler;F. Johnson;D. B. Sloan
  13. J. Amer. Chem. Soc. v.93 E. J. Corey(et al.)
  14. Tetrahedron Letters P. Crabbe;A. Guzman
  15. Z. Anorg. Allg. Chem. v.386 H. Noth;E. Wiberg;L. P.Winter
  16. Advanced Organic Chemistry J. March
  17. Proc. Chem. Soc. G. R. Pettit(et al.)
  18. Tetrahedron Letters N.T. Anh(et al.)
  19. J. Korean. Chem. Soc. v.17 N. M. Yoon;H. J. Lee;J. S. Chung
  20. J. Org. Chem. v.38 N. M. Yoon(et al.)
  21. J. Amer. Chem. Soc. v.72 R. S. Brokaw;E. J. Badin;R. N. Pease
  22. J. Amer. Chem. Soc. v.82 T. L. Jacobs;R. B. Brownfied
  23. J. Chem. Soc. E. B. Leed;J. R. Siegel
  24. J. Korean Chem. Soc. v.19 N. M. Yoon;H. J. Lee;J. S. Chung;J. Kang
  25. J. Korean. Chem. Soc. v.19 N. M. Yoon;J. Kang
  26. J. Korean. Chem. Soc. v.19 N. M. Yoon;J. Kang
  27. M. S. Thesis, Sogang University D. H. Kim
  28. J. Amer. Chem. Soc. v.72 S. W. Chaikin;W. G. Brown
  29. Chem. Commun. H. C. Brown;N. M. Yoon
  30. Israel J. Chem. v.1 H. C. Brown;P. M. Weissman
  31. M. S. Thesis, Sogang University C. S. Kim