Conclusions
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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.
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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.
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3.
Proposals were offered for the nature of the transition states in the reactions of PCl5 with alkenes.
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Literature cited
M. J. S. Dewar, Chem. Soc. Jpn.,18, 279 (1951).
J. Chatt and L. A. Dunkanson, J. Chem. Soc., 2939 (1953).
K. Stallik and J. A. Ibers, J. Am. Chem. Soc.,93, 3779 (1971).
N. M. Rohmen and B. Ross, J. Am. Chem. Soc.,97, 2025 (1975).
G. L. Delker, Yu. Wang, G. D. Stucky, R. L. Lambert, C. K. Haas, and D. Seyferth, J. Am. Chem. Soc.,98, 1779 (1976).
Okamoto Yoshiki and Sakurai Hiroshi, Bull. Chem. Soc. Jpn.,43, 2613 (1970).
Okamoto Yoshiki and Sakurai Hiroshi, J. Jpn. Oil Chem. Soc.,18, 882 (1972).
V. V. Rybkina, V. G. Rozinov, and E. F. Grechkin, Zh. Obshch. Khim.,43, 62 (1973).
A. F. Kolomiets, A. V. Fokin, A. A. Krolevets, and O. V. Bronnyi, Izv. Akad. Nauk SSSR, Ser. Khim., 2552 (1977).
V. G. Rozinov, G. A. Pensionerova, V. I. Glukhikh, and E. F. Grechkin, Zh. Obshch. Khim.,46, 1903 (1976).
F. Freeman, Chem. Rev.,75, 439 (1975).
Additional information
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