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Mechanism of the reaction of vinyl acetate 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.

    We have studied the reaction of vinyl acetate with PC15 in CCl4 and benzene with reactant ratios of 1∶1 and 1∶2. A 1∶2 adduct is formed only at low temperatures (∼0°C) in a solvent that does not solvate it. More forcing conditions or conditions under which phosphorus chlorides are solvated form a 1∶1 adduct; this spontaneously isomerizes to the cyclic product of addition of PCl5 to two donor sites of vinyl acetate, which is catalytically converted to [2-(α,α-dichloroethoxy)-2-chloroethyl]phosphonic dichloride.

Thermolysis of the unsolvated 1∶2 adduct is accompanied by elimination of HCl and formation of a mixture of [2-(α,α-dichloroethoxy)vinyl]phosphonic dichloride and [2-(α-chlorovmyloxy)-2-chloroethyl]phosphonic dichloride.

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Authors
  1. A. F. Kolomiets
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  2. A. V. Fokin
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  3. A. A. Krolevets
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  4. O. V. Bronnyi
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2552–2557, November, 1977.

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Kolomiets, A.F., Fokin, A.V., Krolevets, A.A. et al. Mechanism of the reaction of vinyl acetate with phosphorus pentachloride. Russ Chem Bull 26, 2364–2367 (1977). https://doi.org/10.1007/BF00958728

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  • DOI: https://doi.org/10.1007/BF00958728

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