Abstract
The conversion of 5-hydroxy-2(5H)-furanone into succinic acid in aqueous solution has been detected experimentally for the first time, indicating the possibility of forming and hydrolyzing its previously unknown tautomeric forms. The accelerating effect of increased pH values and temperature on the reaction has been established. A scheme is proposed to form succinic acid from 5-hydroxy-2(5H)-furanone.
Similar content being viewed by others
REFERENCES
V. V. Poskonin,L. A. Badovskaya,S. P. Gavrilova, and V. G. Kul'nevich, Zh. Org. Khim., 25, 1701 (1989).
V. V. Poskonin,L. A. Badovskaya, and A. V. Butin, Zh. Org. Khim., 33, 574 (1997).
W. S. Faber,J. Kok,B. de Lange, and B. L. Feringa, Tetrahedron, 50, 4775 (1994).
F. Faringa,M. R. Martin,M. V. Martin, and A. M. de Guerenu, Heterocycles, 38, 1307 (1994).
P. Oravec,L. Fisera,L. Pronayova, and R. Gazo, Chem. Pap., 46, 104 (1992).
R. E. Valter, Usp. Khim., 42, 1060 (1973).
V. M. Andreev,G. P. Kugatova-Shemyakina, and S. A. Kazaryan, Usp. Khim., 37, 559 (1968).
I. A. Kuzovnikova,L. A. Badovskaya,Ya. I. Tur'yan, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., 737 (1974).
V. V. Poskonin and L. A. Badovskaya, Russian Patent 1715806; Byull. Izobret., No. 4 (1992).
V. V. Poskonin and L. A. Badovskaya, Khim. Geterotsikl. Soedin., 1462 (1991).
V. G. Kul'nevich and L. A. Badovskaya, Khim. Geterotsikl. Soed., 1314 (1978).
F. Feigl, Spot Tests in Organic Analysis (trans. by R. E. Oesper), Elsevier, New York (1960), 675 pp.; [Russian translation], Goskhimizdat, Moscow (1962), p. 323.
Organicum, Vol. 2 [Russian translation], Mir, Moscow (1979), p. 79.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Poskonin, V.V., Badovskaya, L.A. Unusual Conversion of 5-Hydroxy-2(5H)furanone in Aqueous Solution. Chemistry of Heterocyclic Compounds 39, 594–597 (2003). https://doi.org/10.1023/A:1025137914137
Issue Date:
DOI: https://doi.org/10.1023/A:1025137914137