Tautomerism in malonic ester derivatives of s‐triazine

Authors

C. Fredric Reynolds, Duke University
Arthur F. Saari, Michigan Technological University

Document Type

Article

Publication Date

1-1-1975

Department

Department of Chemistry; Department of Chemical Engineering

Abstract

Pmr and uv spectra of tris‐, bis‐ and monomalonic ester derivatives of s‐triazine were studied in chloroform, dioxane, methanol, water, acetonitrile, dimethylsulfoxide, dimethylformamide, and cyclohexylamine. The results indicate that the enaminic structures (I, II and III) predominate in chloroform, dioxane, methanol and water. A small amount of enolate is present in acetonitrile and a larger amount of enolate is present in dimethylsulfoxide, dimethylformamide and cyclohexylamine in the case of the tris‐ and bismalonic ester derivatives of s‐triazine. The conclusion is reached that for these latter compounds in basic solvent, a tautomeric equilibrium exists between the enaminic form and resonance‐stabilized enolate ions.

Publisher's Statement

Copyright © 1975 Journal of Heterocyclic Chemistry. Publisher’s version of record: https://doi.org/10.1002/jhet.5570120216

Publication Title

Journal of Heterocyclic Chemistry

Recommended Citation

Reynolds, C., & Saari, A. (1975). Tautomerism in malonic ester derivatives of s‐triazine. Journal of Heterocyclic Chemistry, 12(2), 295-299. http://doi.org/10.1002/jhet.5570120216
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/3734