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Reaction of phenylchlorocarbene with 2-alkenylfurans and some transformations of the formed adducts

Conclusions

  1. 1.

    2-Alkenylfurans react with phenylchlorocarbene to give furyl-gem-phenylchlorocyclopropanes.

  2. 2.

    Reduction of the furyl-gem-phenylchlorocyclopropanes with sodium in liquid ammonia leads to hydrogenolysus of the cyclopropane ring with the formation of 1-furyl-3-phenylalkanes.

  3. 3.

    The catalytic hydrogenation of the furyl-gem-phenylchlorocyclopropanes in a flow system over Pt/C at 260–265° leads to hydrogenolysis of both the furan and cyclopropane rings with the formation of phenyl-substituted ketones.

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Literature cited

  1. 1.

    V. M. Shostakovskii, M. Ya. Samoilova, M. I. Kravchenko, and O. M. Nefedov, in: New Advances in the Chemistry of Carbenes [in Russian], Nauka (1973), p. 200.

  2. 2.

    V. M. Shostakovskii, M. I. Kravchenko, and O. M. Nefedov, All-Union Symposium on Heterogeneous Catalysis in Synthesis and Transformations of Heterocyclic Compounds. Abstracts of Papers [in Russian], Zinatre, Riga (1972), p. 9.

  3. 3.

    M. L Kravchenko, Dissertation, Moscow (1973).

  4. 4.

    O. M. Nefedov, V. M. Shostakovskii, and M. I. Kravchenko, Izv. Akad. Nauk SSSR, Ser. Khim., 2767 (1974).

  5. 5.

    O. M. Nefedov, V. M. Shostakovskii, M. Ya. Samoilova, and M. I. Kravchenko, Izv. Akad. Nauk SSSR, Ser. Khim., 1590 (1971).

  6. 6.

    D. H. Williams, R. G. Cooks, J. Ronayne, and S. W. Tam, Tetrahedron Lett., 1777 (1968).

  7. 7.

    O. M. Nefedov, R. N. Shafran, and N. N. Novitskaya, Zh. Organ. Khim.,8, 2075 (1972).

  8. 8.

    V. M. Shostakovskii, M. I. Kravchenko, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., 2635 (1973).

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Additional information

The preliminary results are given in [1, 2]; also see [3].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 379–384, February, 1976.

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Nefedov, O.M., Shostakovskii, V.M. & Kravchenko, M.I. Reaction of phenylchlorocarbene with 2-alkenylfurans and some transformations of the formed adducts. Russ Chem Bull 25, 359–364 (1976). https://doi.org/10.1007/BF00922475

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Keywords

  • Hydrogenation
  • Sodium
  • Ammonia
  • Adduct
  • Ketone