Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
권호 표지

Studies on Tropolones (Ⅲ) Structures and Reaction Mechanisms of the Adducts of Dichloroketene and Cyclopentadienes

Tropolone 類에 關한 硏究 (III) Dichloroketene과 Cyclopentadiene 類의 添加物의 構造와 그 反應機構

  • Jae Hu Shim (Department of Chemistry, Hanyang University)
  • Published : 19690300
Download PDF
⟨ Previous Next ⟩

Abstract

The structural investigations on the adducts, formed from dichloroketene with cyclopentadiene, methyl and ethylcyclopentadiene, have been carried out by means of infrared and nuclear magnetic resonance spectroscopy and also by their chemical behaviors. It was confirmed by this study that the adducts were formed by 1, 2-cycloaddition reaction and had the fundamental structure of bicyclo [3. 2. 0]-7,7-dichloro-2-heptene-6-one. These results were well agreed with the hypothesis that a diradical intermediate was formed as the first step in 1, 2-cycloaddition. The reaction mechanism for the process in which tropolones were formed from these adducts was also discussed.

Keywords

References

  1. Organic Reactions v.4 H.L.Holmes
  2. J. Am. Chem. Soc. v.74 D.D. Coffmann;P.L. Barrick;R.D. Cramer;M.S. Raasch
  3. J. Am. Chem. Soc. v.63 B.T. Brooks;G. Wilbert
  4. J. Am. Chem. Soc. v.73 A.T. Blomquist;.J. Kwiatek
  5. J. Am. Chem. soc. v.80 J.J. Drysdale;W.W. Gilbert;H.K. Sinclair;W.H. Shartey
  6. J. Am. Chem. Soc. v.86 P.D. Bartlett;L.K. Montgomery;B. Seidel
  7. J. Org. Chem. v.30 N.J. Turro;P. D. Bartlett
  8. Ber. v.46 H. Staudinger;E. Anthes;H. Schneider
  9. The Systematic Identification of Organic Compounds R.I. Shriner;R.C. Fuson;D.Y. Curtin
  10. The Systematic Identification of Organic Compounds R.I. Shriner;R.C. Fuson;D.Y. Curtin
  11. J. Am. Chem. Soc. v.73 H.C. Brown;R.S. Fletcher;R.B. Johannesen
  12. J. Am. Chem. Soc. v.74 H.C. Brown;M. Borkowski
  13. The Infrared Spectra of Complex Molecules L. J. Bellamy
  14. The Infrared Spectra of Complex Molecules L.J. Bellamy
  15. J. Am. Chem. Soc. v.78 F.V. Brutcher, Jr.;T. Roberts;S.J. Barr;N. Pearson
  16. Anal. Chem. v.35 K. Nukada;O. Yamamoto;T. Suzuki;M. Takeuchi;M. Ohnishi
  17. Anal. Chem. v.36 M.W. Dietrich;R.E. Keller
  18. Chem. Pharm. Bull. v.II S. Yamaguchi;S. Okuda;N. Nakagawa
  19. J.Am. Chem. Soc. v.86 L.K. Montogomery;K. schueller;P. D. Bartlett
  20. J. Am. Chem. Soc. v.80 P.D. Bartlett;R.R. Hiatt
  21. Steric Effects in Organic Chemistry D.J. Cram;M.S. Newman
  22. Organic Chemistry D.J. Cram;G.S. Hammond