Conclusions
-
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.
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.
Potassium hydroxide substantially suppresses the oxidation of the olefin by the peroxydisulfate and facilitates the homolytic alkylation of acids by the olefin.
Similar content being viewed by others
Literature cited
G. I. Nikishin, Yu. N. Ogibin, and A. D. Petrov, Izv. Akad. Nauk SSSR. Otd. Khim. Nauk, 1487 (1961); H. Vogel, Synthesis, 99 (1970).
D. A. House, Chem. Rev., 62, 185 (1962).
A. Ledwith, P. J. Russell, and L. H. Sutcliffe, Proc. Roy. Soc.,A332, 151 (1973); J. Chem. Soc., Perkin II, 630 (1973).
R. O. C. Norman, P. M. Storey, and P. R. West, J. Chem. Soc., B1087 (1970).
D. J. Edge, R. O. C. Norman, and P. M. Storey, J. Chem. Soc., B1096 (1970).
D. Betel and V. Fold, Carbonium Ions [Russian translation], Mir (1970), p. 199.
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).
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).
H. L. Johnson and R. A. Clark, Anal. Chem.,19, 869 (1947).
I. M Kolthoff, Volumetric Analysis [Russian translation], Vol. 3, Goskhimizdat (1961), p. 341.
F. Critchfield, Analysis of Basic Functional Groups inorganic Compounds [Russian translation], Mir (1965), p. 203.
S. R. Sandler and W. Karo, Organic Functional Group Preparations, Vol. 1, Academic Press, New York-London (1968), p. 252.
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1561–1566, June, 1974.
Rights and permissions
About this article
Cite this article
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
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00929657