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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 2
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Original Articles

Synthesis of Hexacyclo [6.5.1.02,7.03,11.04,9.010,14] Tetradeca-5, 12-diene

Pages 279-284 | Received 21 Sep 1989, Published online: 24 Oct 2006

References

  • LeGoff , E. and Oka , S. 1969 . J. Am. Chem. Soc. , 91 : 5665
  • Sedelmeier , G. , Fessner , W‐D. , Pinkos , R. , Grund , C. , Murthy , B. A.R.C. , Hunkler , D. , Rihs , G. , Fritz , H. , Kruger , C. and Prinzbach , H. 1986 . Chem. Ber. , 119 : 3442
  • Chou , T. C. , Chuang , K. S. and Lin , C. T. 1988 . J. Org. Chem. , 53 : 5168
  • Srikrishna , A. and Sunderbabu , G. 1987 . J. Org. Chem. , 52 : 5037
  • Similar strategy was used earlier1b employing ‐pyrone as the diene, which is about 4000 times expensive than HCCP (1988–89, Aldrich catalogue)
  • Reppe , W. , Schlichting , O. , Klager , K. and Toepel , T. 1948 . Liebigs Ann. Chem. , 560 : 1
  • Newcomer , J. S. and McBee , E. T. 1949 . J. Am. Chem. Soc. , 71 : 946 McBee, E.T., Crain, D.L., Crain, R.D., Belohlav, L.R. and Braendlin, H.P., J. Am. Chem. Soc., 1962, 84, 3557
  • Lay , W. P. , Mackenzie , K. , Miller , A. S. and William‐Smith , D. L. 1980 . Tetrahedron , 36 : 3021 Akhtar, I.A., Atkins, R.J., Fray, G.I., Geen, G.R. and King, T.J., Tetrahedron, 1980, 36, 3033
  • At temperatures above 160°C considerably lower yields were realised probably due to the decomposition of the intermediate diene 7

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