E-Z-izomerization of 2-methylenethiazolidin-4-ones / Morzherin Yu.Yu., Kosterina M.F., Berseneva V.S., Dehaen W., Bakulev V.A. // Russian Chemical Bulletin. - 2002. - V. 51, l. 7. - P. 1292-1297.

ISSN:

10665285

Type:

Article

Abstract:

The equilibrium concentrations of E- and Z-isomers of thiazolidin-4-ones containing exocyclic double bonds in positions 2 and 5 of the cycle were determined in DMSO-d6. The influence of the nature of the substituents on the equilibrium position was found. Electron-releasing substituents stabilize the E,Z-configuration and electron-withdrawing substituents stabilize the Z,Z-configuration. The association constants of E- and Z-2-ethoxycarbonylmethylenethiazolidin-4-ones with the sodium cation were determined by 1H NMR spectroscopy.

Author keywords:

Complex formation; E-Z-izomerization; Exocyclic double bond; Nitrogen-containing heterocycles; Sulfur-containing heterocycles

Index keywords:

cation; dimethyl sulfoxide; exocyclic double bond; methyl [2 [2 (1,3 dioxo 1,3 dihydroisoindol 2 yl)ethylidene] 4 oxothiazol 5 ylidene]acetate; methyl [2 [2 (1,3 dioxo 1,3 dihydroisoindol 2 yl)ethylid

DOI:

10.1023/A:1020912932335

Смотреть в Scopus:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0036421157&doi=10.1023%2fA%3a1020912932335&partnerID=40&md5=eb4eedda4737c8b24c48b7f62c829c80

Соавторы в МНС:

Другие поля

Поле	Значение
Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-0036421157&doi=10.1023%2fA%3a1020912932335&partnerID=40&md5=eb4eedda4737c8b24c48b7f62c829c80
Affiliations	Urals State Technical University, 19 ul. Mira, 620002 Ekaterinburg, Russian Federation; Department of Chemistry, University of Leuven, Celestijnenlaan 200F, 3001 Heverlee (Leuven), Belgium
Author Keywords	Complex formation; E-Z-izomerization; Exocyclic double bond; Nitrogen-containing heterocycles; Sulfur-containing heterocycles
Chemicals/CAS	dimethyl sulfoxide, 67-68-5; sodium, 7440-23-5
References	Berseneva, V.S., Tkachev, A.V., Morzherin, Yu.Yu., Dehaen, W., Luyten, I., Toppet, S., Bakulev, V.A., (1998) J. Chem. Soc., Perkin Trans. 1, p. 2133; Guard, J.A.M., Steel, P.J., (1994) Heterocycles, 37, p. 1711; Markovic, R., Baranac, M., (1998) J. Serb. Chem. Soc., 63 (3), p. 165; D'hooge, B., Dehaen, W., (1997) Bull. Soc. Chim. Belg., 106, p. 729; Morzherin, Yu.Yu., Kosterina, M.F., Bezborodov, A.S., Berseneva, V.S., Luyten, I., Dehaen, W., Bakulev, V.A., (2000) Khim. Geterotsikl. Soed., p. 119; (2000) Khim. Geterocycl. Soed., , Engl. Transl; De Boer, J.A.A., Reinhoudt, D.N., Harkema, S., Van Hummel, G.J., De Jong, F., (1982) J. Am. Chem. Soc., 104, p. 4073; Bakulev, V.A., Lebedev, A.T., Dankova, E.F., Mokrushin, V.S., Petrosyan, V.S., (1989) Tetrahedron, 45, p. 7329
Correspondence Address	Morzherin, Yu.Yu.; Urals State Technical University, 19 ul. Mira, 620002 Ekaterinburg, Russian Federation; email: morjerine@htf.ustu.ru
Language of Original Document	English
Abbreviated Source Title	Russ. Chem. Bull.
Source	Scopus