Conclusions
-
1.
Using nitrosodurene as a spin trap, the addition of CCl3 and PhS radicals to substituted alkenylcyclopropanes was studied by EPR. The formation of spin adducts of cyclopropylcarbinyl and allylcarbinyl radicals with nitrosodurene was established.
-
2.
The rate constant of the isomerization of cyclopropylcarbinyl to allylcarbinyl radicals was determined and it was shown that this rearrangement is quite rapid (isomerization constant 106–107 sec−1).
Similar content being viewed by others
Literature cited
E. S. Huyser and J. D. Taliaferro, J. Org. Chem.,28, 3443 (1963).
P. K. Freeman, M. F. Grostic, and F. A. Paymond, J. Org. Chem.,36, 905 (1971).
S. J. Cristol and R. J. Kellman, J. Org. Chem.,36, 1866 (1971).
I. S. Lishanskii, A. G. Zak, N. D. Vinogradova, A. M. Guliev, O. S. Fomina, and A. S. Khachaturov, Vysokomol. Soedin.,A10, 1866 (1968).
I. S. Lishanskii, N. D. Vinogradova, A. G. Zak, A. B. Zvyagina, A. M. Guliev, O. S. Fomina, and A. S. Khachaturov, Zh. Org. Khim.,10, 493 (1974).
A. M. Guliev, A. N. Lemeshev, S. P. Kasimova, and I. S. Lishanskii, Zh. Org. Khim.,19, 346 (1983).
S. S. Huyser and Z. R. Munson, J. Org. Chem.,30, 1436 (1965).
M. Ratier and M. Pereyre, Tetrahedron Lett., 2275 (1976).
S. Terabe, K. Kuruma, and R. Konaka, J. Chem. Soc. Perkin Trans. 2, 1252 (1973).
R. G. Gasanov, A. B. Terent'eva, and R. Kh. Freidlina, Izv. Akad, Nauk SSSR, Ser. Khim., 2628 (1977).
R. G. Gasanov, G. T. Vasil'eva, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim., 817 (1978).
R. G. Gasanov, L. V. Ivanova, and R. Kh. Freidlina, Dokl. Akad. Nauk SSSR,255, 1156 (1980).
P. Schmid and K. U. Ingold, J. Am. Chem. Soc.,100, 2493 (1978).
R. G. Gasanov, Izv. Akad. Nauk, Ser. Khim., 2264 (1980).
J. Macoda and K. U. Ingold, J. Am. Chem. Soc.,101, 4975 (1979).
T. Doba, T. Ichikawa, and H. Yoshida, Bull. Chem. Soc. Jpn.,50, 3158 (1977).
R. G. Gasanov, L. V. Ivanova, N. A. Grigor'ev, A. L. Tumanskaya, and R. Kh. Freidlina, Dokl. Akad. Nauk SSSR,273, 1410 (1983).
B. A. Énglin, N. A. Grigor'ev, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim., 1568 (1972).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1341–1346, June, 1985.
Rights and permissions
About this article
Cite this article
Guliev, A.M., Leraeshev, A.N., Gasanov, R.G. et al. EPR spectroscopic study of free-radical addition of mercaptans and polyhalomethanes to substituted alkenylcyclopropanes by spin trapping. Russ Chem Bull 34, 1227–1231 (1985). https://doi.org/10.1007/BF00956089
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00956089