Abstract
The previously undescribed 3-(1-hydroxy-4-bromo-2-naphthyl)propenal was synthesized. This aldehyde exists primarily in the form of the cyclic 2H-chromene tautomer in the crystalline state, in solutions in nonpolar solvents, and in acetonitrile, ethanol, and acetone. Ring-chain tautomeric equilibrium between the 2H-chromene and quinoid structures is observed in dimethyl sulfoxide.
Similar content being viewed by others
Literature cited
I. M. Andreeva, O. M. Babeshko, E. A. Medyantseva, and V. I. Minkin, Zh. Org. Khim., 15, 1899 (1979).
I. M. Andreeva, E. M. Bondarenko, E. A. Medyantseva, R. G. Pudeyan, and V. I. Minkin, Khim. Geterotsikl. Soedin., No. 5, 610 (1982).
J. H. Billman and J. A. Tonnis, Pharm. Sci., 60, 1188 (1971).
H. Gross, A. Rieche, and B. Mattey, Chem. Ber., 96, 308 (1963).
E. A. Medyantseva, O. M. Babeshko, and V. I. Minkin, Zh. Org. Khim., 12, 837 (1976).
H. Weil and W. Heerdt, Chem. Ber., 55, 228 (1922).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 181–184, February, 1983.
Rights and permissions
About this article
Cite this article
Andreeva, I.M., Bondarenko, E.M., Medyantseva, E.A. et al. Structure and ring-chain tautomerism of 3-(1-hydroxy-4-bromo-2-naphthyl)propenal. Chem Heterocycl Compd 19, 146–149 (1983). https://doi.org/10.1007/BF00506421
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00506421