Ruthenium Catalyzed Synthesis of N-Substituted Perhydroazepine Derivatives

루테늄 촉매를 이용한 N-치환 과수소아제핀 유도체의 합성

  • 심상철 (경북대학교 공과대학 공업화학과) ;
  • 도칠훈 (경북대학교) ;
  • 이승엽 (경북대학교 공과대학 산업화학과) ;
  • 조완호 (경북대학교 공과대학 산업화학과) ;
  • 허근태 (경성대학교)
  • Published : 19901100

Abstract

Primary amines react with 1,6-hexanediol at 180$^{\circ}C$ for 5 h under argon atmosphere in the presence of both $RuCl_3{\cdot}3H_2$O and $PR_3$ to give N-substituted perhydroazepine derivatives in good yields. For aromatic amines such as anilines, $RuCl_3{\cdot}3H_2$O combined with $PPh_3$ showed the highest catalytic activity. On the other hand, in the reaction of aliphatic amines, $RuCl_3{\cdot}3H_2$O combined with $PBu_3$ showed the highest catalytic activity. These differences may be attributed to the difference in the basicity of these amines. Less basic aromatic amines may require less basic phosphines, while more basic aliphatic amines may require more basic phosphines as the ligands.

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References

  1. J. Synth. Org. Jpn. v.36 T. Kamiyama;M. Inoue;S. Enomoto
  2. J. Kor. Chem. Soc. v.33 S. C. Shim;J. S. Lee;C. H. Doh;Y. K. Kwon;Y. K. Yeo
  3. J. Heterocyclic Chem. v.25 S. C. Shim;K. D. Kim;C. H. Doh;T. J. Kim;H. K. Lee
  4. Bull. Chem. Soc. Jpn. v.60 Y. Tsuji;Y. Yokoyama;K. T. Huh;Y. Watanabe
  5. J. Org. Chem. v.50 Y. Tsuji;K. T. Huh;Y. Ohsugi;Y. Watanabe
  6. J. Mol. Cat. v.62 S. C. Shim;C. H. Doh;B. W. Woo;K. T. Huh;W. H. Park;H. S. Lee
  7. Inorg. Synth. v.12 P. S. Hallman;T. A. Stephenson;G. Wilkinson
  8. J. Chem. Soc., Chem. Commun. Y. Sasson;J. Blum
  9. J. Organomet. Chem. v.212 M. F. Lappertand;S. J. Miles
  10. J. Am. Chem. Soc. v.76 F. F. Blicke;N. J. Doorendos
  11. Comprehensive Organic Chemistry v.2 I. O. Sutherland;D. Barton(ed.);W. D. Ollis(ed.)
  12. Comprehensive Organic Chemistry v.4 P. G. Sammes;D. Barton(ed.);W. D. Ollis(ed.)
  13. Chem. Abstract v.76 R. Dupre;L. Calo;Y. Martino
  14. Chem. Abstract v.72 S. Farhat;L. Kelly
  15. Chem. Abstract v.74 J. R. Bottu
  16. Transition Metal Organometallics in Organic Synthesis v.2 H. Alper
  17. J. Am. Chem. Soc. v.76 F. F. Blicke;E. P. Tsao