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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 12, 1982 - Issue 13
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Original Articles

A Facile and Efficient Preparation of Tropone from Di-7-Cycloheptatrienyl Ether Using Trifluoroacetic Acid as a Catalyst

Pages 1021-1026 | Published online: 06 Dec 2006

References

  • Pietra , F. 1973 . Chem. Rev. , 73 : 293 and references cited therein.
  • Radric , P. 1964 . J. Org. Chem. , 29 : 960 Jones, G., J. Chem. Soc., C, 1970, 1230.
  • Ikemi , T. , Nozoe , T. and Sugiyama , H. 1960 . Chem. Ind. (London) , : 923
  • Takase , K. 1977 . “Encyclopedia of Experimental Chemistry,” , Edited by: Tachibana , E. vol. XIV-2 , 904 Tokyo : Maruzen . in this synthetic method, trop-one cannot often be obtained at all since the reaction mixture is apt to polymerize in the flask on the occasion of its distillation. Moreover, we sometimes had the experience that tropone thus obtained changed to a jelly-like polymeric material during storage in a refrigerator.
  • Conrow , K. 1973 . Org. Synth. , Col. Vol. V, 1138; cf. Vol'pin, M. F., Akhrem, I. S., and Kursanov, D. N., Izv. Akad. Nauk SSSR, Ser. Khim., 1957, 760.
  • Nozoe , T. , Takase , K. and Matsumura , H. 1974 . “Comprehensive Organic Chemistry”, , 9th ed. , Edited by: Kotake , M. vol. XIII , 76 Tokyo : Asakura Shoten .
  • The trifluoroacetic acid was added slowly to prevent sudden boiling over, because the reaction is exothermic.
  • Volatile trifluoroacetic acid is removed at this stage, and the recovered 3 can be utilized for another reaction process.

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