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Formation of β-cyclopropyl-substituted vinylcyclopropanes in the catalytic cyclopropene-vinylcarbene isomerization of 3-methyl-3-cyclopropyl-and 3,3-dicyclopropylcyclopropenes in the presence of unsubstituted hydrocarbons

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

Conclusions

  1. 1.

    The reaction of 3,3-dialkyl(cycloalkyl)cyclopropenes with unsaturated hydrocarbons in the presence of CuCl or (PhO)3P·CuCl leads to the cyclopropanation of the hydrocarbon double bond by vinylcarbenes which arise as a result of a cyclopropene-carbene isomerization. In addition to vinylcyclopropanes, the products of the recombination of the vinylcarbenes, namely, the corresponding trienes, are formed.

  2. 2.

    The cyclopropanation of cyclic dienes by vinylcarbenes obtained from cyclopropenes in the presence of CuCl or (PhO)3P·CuCl proceeds with higher yields than in the case of normal alkenes.

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Authors and Affiliations

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

    Yu. V. Tomilov, V. G. Bordakov, N. M. Tsvetkova, A. Ya. Shteinshneider, I. E. Dolgli & O. M. Nefedrov

Authors
  1. Yu. V. Tomilov
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  2. V. G. Bordakov
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  3. N. M. Tsvetkova
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  4. A. Ya. Shteinshneider
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  5. I. E. Dolgli
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  6. O. M. Nefedrov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,. No. 2, pp. 336–343, February, 1983.

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Tomilov, Y.V., Bordakov, V.G., Tsvetkova, N.M. et al. Formation of β-cyclopropyl-substituted vinylcyclopropanes in the catalytic cyclopropene-vinylcarbene isomerization of 3-methyl-3-cyclopropyl-and 3,3-dicyclopropylcyclopropenes in the presence of unsubstituted hydrocarbons. Russ Chem Bull 32, 300–306 (1983). https://doi.org/10.1007/BF00957936

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  • DOI: https://doi.org/10.1007/BF00957936

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