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Mechanism of reaction of 1, 2, 3-triphenylcyclopropene with trifluoroacetic acid

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

Conclusions

  1. 1.

    The triphenylallyl cation, obtained directly in the acid cleavage of 1,2,3-triphenylcyclopropene, was fixed by its quantitative conversion to cis-1,2, 3-triphenyl-1-propene in the presence of a hydride-ion donor, which experimentally confirms the adopted mechanism of the rearrangements in the cyclopropene series under the influence of acids.

  2. 2.

    The opening of the three-membered ring in the studied reaction proceeds stereospecifically, with a disrotator rotation of the substituents on the outside in harmony with the Woodward-Hoffman rule.

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Authors and Affiliations

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

    G. A. Kudryavtseva & O. A. Nesmeyanova

Authors
  1. G. A. Kudryavtseva
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  2. O. A. Nesmeyanova
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2357–2359, October, 1974.

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Kudryavtseva, G.A., Nesmeyanova, O.A. Mechanism of reaction of 1, 2, 3-triphenylcyclopropene with trifluoroacetic acid. Russ Chem Bull 23, 2271–2273 (1974). https://doi.org/10.1007/BF00921303

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  • DOI: https://doi.org/10.1007/BF00921303

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