대한화학회지 (Journal of the Korean Chemical Society)

  • 제18권6호
  • /
  • Pages.437-442
  • /
  • 1974
  • /
  • 1017-2548(pISSN)
  • /
  • 2234-8530(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지

Pentacyclo ($5,3,0,0^{2,5},06{3,9},0^{4,8})-decane-6,10-dione의 합성

Studies on the Synthesis of Pentacyclo ($5,3,0,0^{2,5},06{3,9},0^{4,8})-decane-6,10-dione

  • 정의준 (서울대학교 문리과대학 화학과) ;
  • 장세희 (서울대학교 자연과학대학 화학과) ;
  • Ui Chun Chong (Department of Chemistry, College of Liberal Arts and Sciences, Seoul National University) ;
  • Sae Hee Chang (Department of Chemistry, College of Liberal Arts and Sciences, Seoul National University) ;
  • K.V. Scherer, Jr. (Department of Chemistry, University of Southern California)
  • 발행 : 1974.12.30
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초록

Cyclopentanone을 출발 물질로 하여 60%의 좋은 총 수득률로 pentacyclo ($5,3,0,0^{2,5},06{3,9},0^{4,8})-decane-6,10-dion을 합성하였다. Cyclopentanone 으로부터 그의 ethylene ketal(I)을 합성하여 pyridinium bromide perbromide로서 브롬화시키고 브롬화 ketal(II)을 다시 dehydrobromination 시켜 cyclopentadienone-ethylene ketal의 dimer를 합성하였다. Ethylene ketal의 dimer(III)를 다시 가수분해시켜 dicyclopentadiene-1,8-dione(IV)을 합성하고 이 diketone(IV)을 photochemical cyclization에 의하여 pentacyclo ($5,3,0,0^{2,5},06{3,9},0^{4,8})-decane-6,10-dione(V)을 합성하였다.

Pentacyclo ($5,3,0,0^{2,5},06{3,9},0^{4,8})-decane-6,10-dione was synthesized from the cyclopentanone in good overall yield(60%). Cyclopentanone ethylene ketal(Ⅰ) was brominated with pyridinium bromide perbromide, and the brominated ketal(Ⅱ) was converted to the dimer of cyclopentadienone ethylene ketal(Ⅲ). The ethylene ketal(Ⅲ) was again converted to the dicyclopentadiene-1,8-dione(Ⅳ). Finally, the pentacyclo ($5,3,0,0^{2,5},06{3,9},0^{4,8})-decane-6,10-dione(Ⅴ) was synthesized from the dicyclopentadilene-1,8-dione(Ⅳ) by photochemical cyclization.

키워드

참고문헌

  1. Chem. Ber. v.94 K. Hafner;K. Galiasch
  2. J. Amer. Chem. Soc. v.82 C.H. Depuy;C.E. Lyons
  3. Chem. Ber. v.88 H.W. Wanzlick(et al.)
  4. Chem. Ber. v.87 K. Alder;F.H. Flock
  5. Chem. Ber. v.71 E. Salmi
  6. J. Amer. Chem. Soc. v.87 P.E. Eatonand;R.A. Hudson
  7. J. Org. Chem. v.29 C.H. Depuy(et al.)
  8. Chem. Rev. v.40 Schoberg;Mustofa
  9. J. Amer. Chem. Soc. v.89 H.E. Zimmerman;J.S. Swenton
  10. Helv. Acta. v.53 L. Ulrich(et al.)
  11. J. Amer. Chem. Soc. v.80 Cristol;Snell
  12. J. Chem. Soc. R.C. Cookson(et al.)
  13. Tetrahedron Letter W. Reusch;D.W. Frey
  14. J. Chem. Soc. C. R. Bishop;N.K. Hamer
  15. J. Amer. Chem. Soc. v.93 W.L. Schreiber;W.C. Agosta
  16. J. Amer. Chem. Soc. v.94 A.M. Foster;W.C. Agosta
  17. J. Chem. Soc. Perkin Trans. v.2 N.K. Hamer;C.J. Samuel
  18. Experiment of Organic Chemistry by Fiesre D.C. Heath and Company
  19. Angew. Chem. v.74 E. Vogel;E.G. Wyes