Amination of Organic Azides using Tetracarbonylhydridoferrate(O) as a Reducing Agent(I)

환원시약인 테트라카르보닐철산염(O)을 이용한 유기아지드화물의 아미노화 (제1보)

  • Sang Chul Shim (Department of Industrial Chemistry, Kyungpook National University) ;
  • Kui Nam Choi (Department of Industrial Chemistry, Kyungpook National University)
  • 심상철 (경북대학교 공과대학 공업화학과) ;
  • 최귀남 (경북대학교 공과대학 공업화학과)
  • Published : 1985.08.20

Abstract

Organic azides were reduced to organic amines in the presence of tetracarbonylhydridoferrate(O) as a highly selective reducing agent at room temperature under carbon monoxide atmosphere. Particularly, benzoylazide gave ethylphenylcarbamate at room temperature but gave benzamide quantitatively at -40$^{\circ}$ in the presence of tetracarbonylhydridoferrate under carbon monoxide atmosphere.

유기아지드화물은 일산화탄소대기압하, 실온에서 높은 선택적 환원시약인 테트라카르 보닐철산염의 존재하에서 높은 수득율의 아민으로 환원되었다. 특히 벤조일아지드는 동일시약내 일산화탄소 대기압 실온에서는 에틸페닐카바메이트를 주나, -40$^{\circ}$에서는 정량적으로 벤즈아미드가 얻어졌다.

Keywords

References

  1. The chemistry of theazido group T. Sheradsky;S. Patai
  2. Synthesis E.J. Corey;K.C. Nicolaou;R.D. Balanson;Y. Machida
  3. J. Amer. Chem. Soc. v.73 J.H. Boyer
  4. Bciohem. v.18 B. Stanovic;M. Tisler;S. Polac;Grcner
  5. Synthesis T. Adaki;Y. Yamada;I. Inoue
  6. Synthesis S. Polanc;B. Stanovic;M. Tisler
  7. Tetrahedron Lett. M. Hedayatullah;A. Guy
  8. Tetrahedron Lett. H. Bayley;D.N. Standring;J.R. Knowles
  9. J. Org. Chem. v.23 P.A. Smith
  10. J. Org. Chem. v.47 F. Rolla
  11. Tetrahedron Lett. M. Vaultier;N. Knouzi;R. Carrie
  12. J. Amer. Chem. Soc. v.79 H.W. Stenberg;R. Markby;I. Wender
  13. Bull. Chem. Soc. Jpn. v.41 Y. Takegami;Y. Watanabe;I. Kanaya;T. Mitsudo;H. Masada
  14. J. Org. Chem. v.37 R. Noyori;I. Umeda;T. Ishigami
  15. J. Org. Chem. v.41 no.806 H. Alper
  16. Tetrahedron Lett. G. CaineIli;M. Panunzio;A. Umani-Ronchi
  17. Chem. Lett. Y. Watanabe;S.C. Shim;T. Mitsudo;M. Yamashita;Y. Takegami
  18. Bull. Chem. Soc. Jpn. v.49 Y. Watanabe;S.C. Shim;T. Mitsudo;M. Yamashita;Y. Takegami
  19. Tetrahedron v.35 Y. Watanabe;S.C. Shim;H. Uchida;T. Mitsudo;Y. Takegami
  20. Bull. Kor. Chem. Soc. v.3 S.C. Shim;Y. Watanabe
  21. Organic Functional Group Preparation v.2 S.R. Sandler;W. Karo
  22. Ber. v.55 T. Curtius;G. Ehrhart
  23. J. Amer. Chem. Soc. v.73 P.A. Smith;H.C. Brown
  24. Org. Synth. v.4 P.A. Smith;J.H. Boyer
  25. J. Amer. Chem. Soc. v.74 J.H. Boyer;D. Straw
  26. Ber. v.26 E. Neolting;O. Michel
  27. J. Amer. Chem. Soc. v.77 O.C. Derber;M.T. Edmison
  28. J. Amer. Chem. Soc. v.81 P. Krumholtz;H.A.M. Stettiner
  29. Bull. Chem. Soc. Jpn. v.49 Y. Watanabe;S.C. Shim;T. Mitsudo;M. Yamashita;Y. Takegami
  30. v.48 Y. Watanabe;T. Mitsudo;M. Yamashita;Y. Takegami
  31. Reagent for organic synthesis v.1 M. Fieser;L. Fieser
  32. J. Organometallic Chem. v.216 G.L. Monica;S. Cenini
  33. Inorg. Chem. v.18 D.J. Darenberg;M.Y. Darenberg;N. Walker;J.A. Froelich;H.L.C. Barros
  34. J. Amer. Chem. Soc. v.99 R.M. Laine;G.C. Rinker;P.C. Ford