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Peroxydisulfate-initiated reactions of 1-heptene with acetic and propionic acids

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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 sodium peroxydisulfate-initiated reaction of 1-heptene with acetic and propionic acids at 90–105°, as well as the effect of potassium hydroxide on this reaction.

  2. 2.

    We were the first to discover that an olefin can be oxidized by a peroxydisulfate. The composition and character of the oxidation products are in agreement with the mechanism of a one-electron oxidation of the olefin and the formation of the cation-radical\(R--CH--\mathop {CH_2 }\limits^ + \) as the primary reaction product.

  3. 3.

    Potassium hydroxide substantially suppresses the oxidation of the olefin by the peroxydisulfate and facilitates the homolytic alkylation of acids by the olefin.

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Literature cited

  1. G. I. Nikishin, Yu. N. Ogibin, and A. D. Petrov, Izv. Akad. Nauk SSSR. Otd. Khim. Nauk, 1487 (1961); H. Vogel, Synthesis, 99 (1970).

  2. D. A. House, Chem. Rev., 62, 185 (1962).

    Google Scholar 

  3. A. Ledwith, P. J. Russell, and L. H. Sutcliffe, Proc. Roy. Soc.,A332, 151 (1973); J. Chem. Soc., Perkin II, 630 (1973).

    Google Scholar 

  4. R. O. C. Norman, P. M. Storey, and P. R. West, J. Chem. Soc., B1087 (1970).

  5. D. J. Edge, R. O. C. Norman, and P. M. Storey, J. Chem. Soc., B1096 (1970).

  6. D. Betel and V. Fold, Carbonium Ions [Russian translation], Mir (1970), p. 199.

  7. M. Julia, Accounts Chem. Res.,4, 386 (1971); J. C. Chottard and M. Julia, Tetrahedron,28, 5615 (1972); L. M. Montgomery, J. W. Matt, and J. R. Webster, J. Am. Chem. Soc.,89, 923, 934, 6556 (1967); H. Labenheim and W. Bartok, J. Am. Chem. Soc.,89, 1786 (1967).

    Google Scholar 

  8. J. M. Surzer and P. Teissier, Bull. Soc. Chim. France, 3060 (1970); D. D. Tanner and F. C. P. Law, J. Am. Chem. Soc.,91, 7535 (1969); S. Julia, Compt. Rend.,273C, 174 (1971); A. L. J. Beckwithand C. B. Thomas, J. Chem. Soc., Perkin II, 861 (1973); A. L. J. Beckwith and P. K, Tindal, Australes. J. Chem.,24, 2099 (1971); C. L. Karl, E. J. Maas, and W. Reusch, J. Org. Chem.,37, 2834 (1972); S. N. Lewis, J. J. Miller, and S. Winstein, J. Org. Chem.,37, 1478 (1972); G. I. Nikishin, E. K. Starostin, and B. A. Golovin, Izv. Akad. Nauk SSSR, Ser. Khim., 825 (1973).

  9. H. L. Johnson and R. A. Clark, Anal. Chem.,19, 869 (1947).

    Google Scholar 

  10. I. M Kolthoff, Volumetric Analysis [Russian translation], Vol. 3, Goskhimizdat (1961), p. 341.

  11. F. Critchfield, Analysis of Basic Functional Groups inorganic Compounds [Russian translation], Mir (1965), p. 203.

  12. S. R. Sandler and W. Karo, Organic Functional Group Preparations, Vol. 1, Academic Press, New York-London (1968), p. 252.

    Google Scholar 

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1561–1566, June, 1974.

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Nikishin, G.I., Ogibin, Y.N. & Rakhmatullina, L.K. Peroxydisulfate-initiated reactions of 1-heptene with acetic and propionic acids. Russ Chem Bull 23, 1479–1483 (1974). https://doi.org/10.1007/BF00929657

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  • DOI: https://doi.org/10.1007/BF00929657

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