Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
권호 표지

Selective Reduction of ${\alpha},\;[\beta}$-Epoxy Ketones with Zinc Borohydride

수소화붕소 아연에 의한 에폭시케톤의 선택환원

  • Nung Min Yoon (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) ;
  • 강재효 (서강대학교 이공대학 화학과)
  • Published : 1975.10.30
Download PDF
⟨ Previous Next ⟩

Abstract

Reduction of epoxy ketones with zinc borohydride proceeds selectively to the corresponding epoxy alcohols in good yields. Thus we obtained 3,4-epoxy-4-methyl-2-pentanol($79.8{\%}$), trans-isophorol oxide ($89.5{\%}$), trans-2-benzal-cyclohexanol oxide ($84.1{\%}$) and trans-chalcol oxide ($97.9{\%}$, crude) from the corresponding epoxy ketones.

에폭시케톤을 수소화붕소 아연으로 환원하면 카르보닐기만 선택적으로 확원되어 해당하는 에폭시알코올을 좋은 수득율로 얻을수 있음을 알 수 있었다.

Keywords

References

  1. M.S. Thesis, Sogang University H.K. Kim
  2. J. Chem. Soc. H.B. Henberst;R.A.L. Wilson
  3. J. Chem. Soc.(B) G.H. Wheatman(et al.)
  4. Z. Anorg. Allg. Chem. v.386 E. Wiberg(et al.)
  5. J. Org. Chem. v.23 G.B. Payne
  6. Organic Synthesis Coll v.IV H.O. House(et al.)
  7. J. Amer. Chem. Soc. v.78 H.O. House(et al.)
  8. J. Amer. Chem. Soc. v.77 H.H. Wasserman(et al.)
  9. J. Org. Chem. v.38 S. Thoren(et al.)
  10. C. R. Acad. Sci. Paris. Ser. C v.266 P Chautemps;J.L. Pierre;P. Arnold
  11. Chem. Abstr. v.69 P Chautemps;J.L. Pierre;P. Arnold
  12. Chem. Rev v.59 R.E. Parker;N.S. Isaacs
  13. J. Amer. Chem. Soc. v.79 H.O. House;D.J. Reif
  14. J. Amer. Chem. Soc. v.83 H.O. House;D.J. Reif
  15. J. Amer. Chem. Soc. v.71 S.W. Chaikin;W.G. Brown
  16. Tetrahedron Letters V. Hach(et al.)
  17. J. Chem. Soc. v.C A. Akisanya(et al.)
  18. J. Amer. Chem. Soc. v.82 W.J. Gensler;F.Johnson;A.D.B. Slown
  19. J. Amer. Chem. Soc. v.85 W.J. Gensler;F.Johnson;A.D.B. Slown
  20. N.M. Yoon;J. Kang
  21. Tetrahedron v.1 H.C. Brown;O.H. Wheeler;K. Ichigawa
  22. Boranes in Organic Chemistry H.C. Brown
  23. Tetrahedron Letters J.L. Pierre;P. Chautemps
  24. J. Org. Chem. v.29 K. Tori;T. Komeo;T. Nakagawa