가스크로마토그라피 분석을 통한 $\alpha$-브로모-$\omega$ -플루오로알칸의 효율적 합성

Effective Synthesis of $\alpha$--Bromo-$\omega$ -fluoroalkane with Analysis of Gas-chromatography

  • 발행 : 19950500

초록

디브로모알칸, AgF 및 tetrabutylammoniumbromide(TBABr)를 acetonitrile 용매하에서 $82^{\circ}C$에서 20분간 반응시켜 19~55%의 수율로 $\alpha$-브로모-$\omega$-플르오르알칸을 합성하였다. 반응 조건은 가스 크로마토그라피를 이용하여 조절하였으며, 반응 생성물인 $\alpha$-브로모-$\omega$-플르오르알칸, 디플르오로알칸, 플르오로알켄 및 브로모알켄을 1^H$ NMR 및 $19^F$ NMR로 확인하였다.

$\alpha$-Bromo-$\omega$-fluoroalkanes are synthesized in 19∼55% yields from the reactions of dibromoalkanes with AgF and TBABr in acetonitrile at $82^{\circ}C$ for 20 minutes. The reaction is monitored with gas-chromatography. 1^H$ NMR and $19^F$ NMR-Spectrometer are used for identification of $\alpha$-Bromo-$\omega$-fluoroalkanes, difluoroalkane, fluoroalken and bromoalkene.

키워드

참고문헌

  1. Organic Reaction v.21 Sharts, C. M.;Sheppard, W. A.
  2. Organic Reaction v.35 Hudlicky, M.
  3. Organic Reaction v.34 Wang, J. C. L.
  4. Angew. Chem. v.93 Gerstenberger, M. R. C.;Haas, A.
  5. J. Fluorine Chem. v.15 Franz, F. R.
  6. J. Org. Chem. v.44 Kollonitisch, J.;Marburg. S.;Perkins, L. M.
  7. Tetrahedron Lett. v.26 Clark, J. H.;Smith, D. K.
  8. J. Org. Chem. v.40 Middleton, W. J.
  9. Chemi. Commun. Landini, D.;Montanari, F.;Rolla, F.
  10. Ber. Dtsch. Chem. Ges. v.69 Ruff, D.
  11. J. Am. Chem. Soc. v.58 Henne, A. L.;T. Midgley, T.
  12. J. Org. Chem. v.49 Cox, D. P.;Terpinski, J.;Lawrynowicz, W.
  13. J. Amer. Chem. Soc. v.95 Starks, C. M.;Owens, R. M.
  14. Synthesis Docks, J.
  15. Angew. Chem. v.84 Pedersen, J. C.;Frensdorff, H. K.
  16. Trtrahedron Lett. Dietrich, B.;Lehn, J. M.;Sauvage, J. P.
  17. J. Org. Chem. USSR v.13 Yagupol'skii, L. M.;Kondratenko, N. V.;Popov, V. I.
  18. Bull. Chem. Soc. Jpn. v.56 Yamawaki, J.;Kawate, T.;Ando, T.;Hanafusa, T.
  19. J. Chem. Soc., Chem. Commun. Zupan, M.;Pollak, A.
  20. J. Org. Chem. v.59 Wright, S. W.;Hageman, D. L.;McClure, L. D.
  21. J. Org. Chem. v.15 Hoffmann, F. W.
  22. J. Org. Chem. v.21 Pattison, F. L. M.;Howell, W. C.;McNamara, A. J.;Schneider, J. C.;Walker, J. F.
  23. Anal. Chem. v.55 Larson, 6. J. R.;Pfeiffer, C. D.
  24. J. Ameri. Chem. Soc. v.96 Liotta, C. L.;Harris, H. P.
  25. J. Chem. Rev. v.69 Parker, A.