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Solvent effect on the reaction 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.

    The solvent effect on the conditions and course of reactions of PCl5 with alkenes was studied. The temperature at the onset of these reactions decreased with increasing polarity of the medium and donor properties of the solvents.

  2. 2.

    The reaction pathways for PCl5 with alkenes are determined not only by the alkene structure, as had been assumed previously, but also by the temperature conditions for the condensation and decomposition of the adducts and also by the solvent properties. Depending on these factors, the final reaction products may be chloroalkenes, dichloroalkanes, phosphorylated alkenes, or 2-chloroalkanes.

  3. 3.

    Proposals were offered for the nature of the transition states in the reactions of PCl5 with alkenes.

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Literature cited

  1. M. J. S. Dewar, Chem. Soc. Jpn.,18, 279 (1951).

    Google Scholar 

  2. J. Chatt and L. A. Dunkanson, J. Chem. Soc., 2939 (1953).

  3. K. Stallik and J. A. Ibers, J. Am. Chem. Soc.,93, 3779 (1971).

    Google Scholar 

  4. N. M. Rohmen and B. Ross, J. Am. Chem. Soc.,97, 2025 (1975).

    Google Scholar 

  5. G. L. Delker, Yu. Wang, G. D. Stucky, R. L. Lambert, C. K. Haas, and D. Seyferth, J. Am. Chem. Soc.,98, 1779 (1976).

    Google Scholar 

  6. Okamoto Yoshiki and Sakurai Hiroshi, Bull. Chem. Soc. Jpn.,43, 2613 (1970).

    Google Scholar 

  7. Okamoto Yoshiki and Sakurai Hiroshi, J. Jpn. Oil Chem. Soc.,18, 882 (1972).

    Google Scholar 

  8. V. V. Rybkina, V. G. Rozinov, and E. F. Grechkin, Zh. Obshch. Khim.,43, 62 (1973).

    Google Scholar 

  9. A. F. Kolomiets, A. V. Fokin, A. A. Krolevets, and O. V. Bronnyi, Izv. Akad. Nauk SSSR, Ser. Khim., 2552 (1977).

  10. V. G. Rozinov, G. A. Pensionerova, V. I. Glukhikh, and E. F. Grechkin, Zh. Obshch. Khim.,46, 1903 (1976).

    Google Scholar 

  11. F. Freeman, Chem. Rev.,75, 439 (1975).

    Google Scholar 

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2108–2114, September, 1979.

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Kolomiets, A.F., Fokin, A.V., Krolevets, A.A. et al. Solvent effect on the reaction of alkenes with phosphorus pentachloride. Russ Chem Bull 28, 1941–1945 (1979). https://doi.org/10.1007/BF00952484

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  • DOI: https://doi.org/10.1007/BF00952484

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