Abstract
2-Phenylimino derivatives of 1,3-thiazine (I), 1,3-oxazine (I), pyrrolidine (II), piperidine (III), and hexahydroazepine (IV), as well as N-methylisatinα-anils (V), were studied. It is shown on the basis of the PMR spectra that I–IV exist in the anti form. In contrast to them, N-methylisatinα-anils exist in the form of two spatial isomers. The rates and energy barriers of syn-anti isomerization in the molecules of these compounds were determined. On the basis of the data obtained it was established that isomerization at the C=N bond is realized via an inversion mechanism.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
A. P. Engoyan, Yu. N. Sheinker, T. F. Vlasova, L. A. Ignatova, and A. E. Gekhman, Khim. Geterotsikl. Soedin., No. 7, 921 (1975).
E. M. Peresleni, A. P. Engoyan, Yu. N. Sheinker, T. D. Zotova, L. A. Ignatova, and B. V. Unkovskii, Khim. Geterotsikl. Soedin., No. 3, 346 (1977).
H. Kessler, P. F. Bley, and D. Leibfritz, Tetrahedron,27, 1687 (1971).
H. Shanan-Atidi and K. H. Bar-Eli, J. Phys. Chem.,74, 961 (1970).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 225–227, February, 1978.
Rights and permissions
About this article
Cite this article
Engoyan, A.P., Sheinker, Y.N., Vlasova, T.F. et al. Spatial isomerism in the N-methylisatin α-anil series. Chem Heterocycl Compd 14, 181–183 (1978). https://doi.org/10.1007/BF00945331
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00945331