Conclusions
The tautomeric transformation of azinylmethanes in neutral solvents proceeds by an intermolecular, ionic dissociative mechanism. The kinetic isotope effect found indicates that the rate-limiting step is either the formation or breakage of a C-H bond in the aromatic tautomeric form.
Similar content being viewed by others
Literature cited
O. P. Petrenko, V. V. Lapachev, and V. P. Mamaev, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim.,3, 117 (1983).
N. S. Zefirov and S. S. Trach, Zh. Org. Khim.,12, 197 (1976).
O. Benaude, M. Chevrier, and J.-E. Dubois, J. Am. Chem. Soc.,101, 2423 (1979).
R. P. Bell, The Proton in Chemistry, Cornell Univ. Press (1973).
O. A. Reutov, I. P. Beletskaya, and K. P. Butin, CH-Acids [in Russian], Nauka, Moscow (1980).
V. V. Lapachev, O. A. Zagulyaeva, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 3, 395 (1977).
Author information
Authors and Affiliations
Additional information
For communication 8, see [1].
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1032–1037, May, 1983.
Rights and permissions
About this article
Cite this article
Petrenko, O.P., Storozhenko, V.G., Lapachev, V.V. et al. Tautomerism of azine derivatives 9. The mechanism of the 1, 3-prototropic transformation of azinylmethanes. Russ Chem Bull 32, 935–939 (1983). https://doi.org/10.1007/BF00956142
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00956142