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Synthesis of 1, 1-dicyclofentylethane and 1, 2-dicyclopentylpropane from cyclopentadiene

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Summary

  1. 1.

    A study was made of the reaction between 3-chlorocyclopentene and ethyl acetate in presence of magnesium, and it was shown that the main reaction is the condensation of two 3-chlorocyclopentene molecules with formation of bi-2-cyclopenten-1-yl; the yield of 1,1-di (2-cyclopenten-1-yl)ethanol does not exceed 5%.

  2. 2.

    1,1-Dicyclopentylethane was prepared for the first time by two methods: A) hydrogénation of l-(2-cyclopenten-l-yl)-l-cyclopentylethane prepared by the Grignard-Wurtz reaction from (l-bromoethyl)cyclopentane and 3-chloropentene, and B) hydrogenation of 6-cyclopentyl-6-methylfulvene synthesized from cyclopentadiene and cyclopentyl methyl ketone.

  3. 3.

    Apart from those mentioned above, we prepared and characterized the following previously undescribed compound: 1,1-di (2-cyclopenten-l-yl)ethanol, α-methylcyclopentanemethanol, (1-bromoethyl)cyclopentane, l-(2-cyclopenten-1-yl)-1-cyclopentylethane, (2-bromopropyl)cyclopentane, and 2-(2-cyclopenten-1-yl)-1-cyclo-pentylpropane.

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Stanko, V.I., Plate, A.F. Synthesis of 1, 1-dicyclofentylethane and 1, 2-dicyclopentylpropane from cyclopentadiene. Russ Chem Bull 8, 103–107 (1959). https://doi.org/10.1007/BF00914224

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Keywords

  • Hydrogenation
  • Methyl
  • Acetate
  • Magnesium
  • Ethyl