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Transformations of 2-(2-methylcyclopropyl) furan and 2-(2-cyclopropylcyclopropyl) furan under catalytic hydrogenation conditions

  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    The hydrogenation of 2-(2-methylcyclopropyl)- and 2-(2-cyclopropylcyclopropyl)-furans at 150° in a flow system in presence of a 13− palladized charcoal catalyst goes with the formation of 2-butyl- and 2-hexyl-tetrahydro furans, respectively.

  2. 2.

    Under these conditoins the hydrogenation of the furan nucleus in the bi- and tri-cyclic systems that we have investigated goes just as smoothly as in the case of simple alkylfurans, but it is accompanied by opening of the cyclopropane ring with simultaneous addition of hydrogen at the place of rupture.

  3. 3.

    In the 2-(2-methylcyclopropyl)- and 2-(2-cyclopropylcyclopropyl)-furan molecules the opening of the cyclopropane ring occurs at the bond between the least hydrogenated carbon atoms.

  4. 4.

    A method is proposed for the preparation of pure 2-(2-methylcyclopropyl) furan.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences, USSR

    N. I. Shuikin, A. D. Petrov, V. G. Glukhovtsev & R. A. Karakhanov

Authors
  1. N. I. Shuikin
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  2. A. D. Petrov
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  3. V. G. Glukhovtsev
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  4. R. A. Karakhanov
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Shuikin, N.I., Petrov, A.D., Glukhovtsev, V.G. et al. Transformations of 2-(2-methylcyclopropyl) furan and 2-(2-cyclopropylcyclopropyl) furan under catalytic hydrogenation conditions. Russ Chem Bull 12, 467–469 (1963). https://doi.org/10.1007/BF00844404

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  • DOI: https://doi.org/10.1007/BF00844404

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