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Reactivity of adducts of alkenes with phosphorus pentachloride

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

Conclusions

  1. 1.

    A study was made of the effect of the nature of the solvent and the temperature conditions on the direction of the reactions of the alkene · 2PCl5 adducts with nucleophilic reagents.

  2. 2.

    Depending on the solvent, temperature, and the structure of the alkene, nucleophilic agents cause either dephosphorylation of the adducts with the liberation of PCl3, or they lead to either the vinyl substitution products or the products of addition to the C=C bond of the alkene.

  3. 3.

    The dephosphorylation of the adducts under the influence of nucleophilic agents is suppressed by nonpolar solvents with weak electrophilic properties or at low temperatures.

  4. 4.

    The obtained additional experimental data are in agreement with the epiphosphoranium structure of the adducts.

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Literature cited

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Authors
  1. A. A. Krolevets
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  2. A. F. Kolomiets
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  3. A. V. Fokin
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  4. P. V. Petrovskii
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 897–904, April, 1980.

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Krolevets, A.A., Kolomiets, A.F., Fokin, A.V. et al. Reactivity of adducts of alkenes with phosphorus pentachloride. Russ Chem Bull 29, 644–651 (1980). https://doi.org/10.1007/BF00961622

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  • DOI: https://doi.org/10.1007/BF00961622

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