Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Studies on Tropolones (Ⅰ) The Synthesis of 4-Ethyltropolone from Cyclopentadiene and Its Spectroscopic Characteristics

Tropolone 類에 關한 硏究 (I) Cyclopentadiene으로부터 4-Ethyltropolone의 合成과 그 分光學的 特性

  • Jae Hu Shim (Department of Chemistry, Hanyang University)
  • Published : 19690300
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Abstract

4-Ethyltropolone has been prepared in three steps from cyclopentadiene by a dichloroketene process, and at the same time, a comparison has also been made with the case of tropolone synthesis. In the addition reaction of dichloroketene to cyclopentadiene as well as to ethylcyclopentadiene, and also in the separation of cycloadducts from reaction mixture, the best results were given by prevention of the reactants from dimerization. Under these condition, the yields of cycloadducts were around 70% for both. Tropolone and 4-ethyltropolone were obtained in the yield of 51% and 32%, respectively, by hydrolysis of cycloadducts with potassium acetate in aqueous acetic acid. These results revealed that the steric effect of ethylgroup was more sensitive to the hydrolysis than to the cycloaddition reaction. A comparison of UV, IR and NMR spectroscopic results of 4-ethyltropolone with those of tropolone was also made together with a brief discussion of the tropolone ring system and ethylgroup effect.

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References

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