Abstract
The existence of amine-imine tautomerism in 2-phenylaminothiazolin-4-ones was confirmed by comparison of the IR and UV spectra of these compounds with N-methyl model compounds with amine and imine structures. It is shown that the temperature changes in the PMR spectra are associated with syn-anti isomerization relative to the exocyclic CN bond. The kinetic parameters of this isomerization were calculated, and it was established that it is realized in the imine form via an inversion mechanism.
Similar content being viewed by others
Literature cited
S. M. Ramsh, K. A. V'yunov, I. Ginak, and E. G. Sochilin, Khim. Geterotsikl. Soedin., No. 6, 775 (1972).
H. Najer, R. Giudicelly, C. Morel, and J. Menim, Bull. Soc. Chim. France,5, 10022 (1963).5, 1022 (1963).
S. M. Ramsh, K. A. V'yunov, A. I. Ginak, and E. G. Sochilin, Zh. Org. Khim.,9, 412 (1973).
E. M. Peresleni, Yu. N. Sheinker, N. P. Zosimova, and Yu. I. Pomerantsev, Zh. Fiz. Khim.,37, 2713 (1963).
A. P. Engoyan, T. F. Vlasova, Yu. N. Sheinker, and I. I. Chizhevskaya, Dokl. Akad. Nauk, Ser. Khim.,20, 1099 (1973).
H. Kessler, P. F. Bley, and D. Liebfritz, Tetrahedron,27, 1687 (1971).
D. Kast, E. H. Carlson, and M. Raban, Chem. Commun., No. 13, 656 (1971).
F. C. Brown, Chem. Rev.,61, 466 (1961).
F. B. Dains and F. Eberly, J. Am. Chem. Soc.,55, 3859 (1933).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 190–195, February, 1978.
Rights and permissions
About this article
Cite this article
Engoyan, A.P., Peresleni, E.M., Vlasova, T.F. et al. Tautomerism and spatial isomerism in the 2-phenylaminothiazolin-4-one series. Chem Heterocycl Compd 14, 148–153 (1978). https://doi.org/10.1007/BF00945327
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00945327